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1. Functionalization of 9-thioxanthone at the 1-position: From arylamino derivatives to [1]benzo(thio)pyrano[4,3,2-de]benzothieno[2,3-b]quinolines of biological interest

Author: Laurent Picot, Blandine Baratte, Mohamed Souab, Raphaël E. Duval, Rémy Le Guével, Stéphane Bach, Florence Mongin, Pascale Moreau, Vincent Dorcet, Valérie Thiéry, Thierry Roisnel, Olivier Mongin, Nahida Mokhtari Brikci-Nigassa, Sandrine Ruchaud, William Erb, Ghenia Bentabed-Ababsa, Lionel Nauton, PICOT, Laurent, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Institut de Chimie de Clermont-Ferrand (ICCF), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Clermont Auvergne (UCA)-Institut national polytechnique Clermont Auvergne (INP Clermont Auvergne), Université Clermont Auvergne (UCA)-Université Clermont Auvergne (UCA), SIGMA Clermont (SIGMA Clermont), Laboratoire Lorrain de Chimie Moléculaire (L2CM), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés (LIENSs), La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS), Plate-forme de criblage d'inhibiteurs de protéines kinases=Kinase Inhibitor Specialized Screening facility (KISSf), Fédération de recherche de Roscoff (FR2424), Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biologie Intégrative des Modèles Marins (LBI2M), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Plate-forme ImPACcell (ImPACcell), Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Biosit : biologie, santé, innovation technologique (SFR UMS CNRS 3480 - INSERM 018), Université de Rennes (UR)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique ), Cancéropôle Grand Ouest, Centre National de la Recherche Scientifique, European Regional Development Fund, Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), SIGMA Clermont (SIGMA Clermont)-Institut de Chimie du CNRS (INC)-Université Clermont Auvergne [2017-2020] (UCA [2017-2020])-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), Phophorylation de protéines et Pathologies Humaines (P3H), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, Institut de Chimie des Substances Naturelles (ICSN), Institut de Chimie du CNRS (INC)-Université Paris-Saclay-Centre National de la Recherche Scientifique (CNRS), Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés - UMR 7266 (LIENSs), Institut national des sciences de l'Univers (INSU - CNRS)-La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS), and Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Centre National de la Recherche Scientifique (CNRS)-Structure Fédérative de Recherche en Biologie et Santé de Rennes ( Biosit : Biologie - Santé - Innovation Technologique )
Subjects: [SDV.SP.MED] Life Sciences [q-bio]/Pharmaceutical sciences/Medication, Molecular model, Xanthones, [SDV]Life Sciences [q-bio], [CHIM.THER] Chemical Sciences/Medicinal Chemistry, Thio, Sequence (biology), [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 01 natural sciences, Biochemistry, Fluorescence, chemistry.chemical_compound, Aniline, Thioxanthone, [SDV.SP.MED]Life Sciences [q-bio]/Pharmaceutical sciences/Medication, Drug Discovery, [CHIM]Chemical Sciences, Amines, Melanoma cells, [SDV.BBM.BC]Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], Kinase inhibition, Molecular Biology, [SDV.BBM.BC] Life Sciences [q-bio]/Biochemistry, Molecular Biology/Biochemistry [q-bio.BM], ComputingMilieux_MISCELLANEOUS, Molecular Structure, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, N-arylation, Organic Chemistry, Bond formation, [CHIM.ORGA] Chemical Sciences/Organic chemistry, Combinatorial chemistry, [SDV.MP.BAC]Life Sciences [q-bio]/Microbiology and Parasitology/Bacteriology, 0104 chemical sciences, 010404 medicinal & biomolecular chemistry, chemistry, Thioxanthenes, Quinolines, Surface modification, Copper
Abstract: International audience; Original 1-amino substituted thioxanthone derivatives were easily prepared from the bare heterocycle by a deprotometalation-iodolysis-copper-catalyzed CeN bond formation sequence. This last reaction delivered mono-or/and diarylated products depending on the aniline involved. 1-Amino-9-thioxanthone was also prepared and reacted with 2-iodoheterocycles. Interestingly, while 1-(arylamino)-9-thioxanthones could be isolated, their subsequent cyclization was found to deliver original hexacyclic derivatives of helicoidal nature. Evaluation of their photophysical properties revealed high fluorescence in polar media, indicating potential applications for biological imaging. These compounds being able to inhibit PIM1 kinase, their putative binding mode was examined through molecular modeling experiments. Altogether, these results tend to suggest the discovery of a new family of fluorescent PIM inhibitors and pave the way for their future rational optimization.
Published: 2020
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2. Surface engineering of polystyrene–cerium oxide nanocomposite thin films for refractive index enhancement

Author: Guillaume Vignaud, Yves Grohens, Aparna Beena Unni, Nandakumar Kalarikkal, Soney Varghese, Jean-Paul Chapel, Khadidja Taleb, Jemy James, Institut de Recherche Dupuy de Lôme (IRDL), Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Centre National de la Recherche Scientifique (CNRS), International and Inter University Centre for Nanoscience and Nanotechnology, Mahatma Gandhi University, Université Oran 1 Ahmed Ben Bella, Laboratoire de Synthèse Organique Appliquée (LSOA), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Centre de Recherche Paul Pascal (CRPP), Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), School of Pure and Applied Physics, Mahatma Gandhi University, School of Nano Science and Technology, and CNRS, Republic of France and DST-Govt. of India for funding through Nanomission, FIST and PURSE programs, UGC-Govt. of India and the funding from BRNS- DAE (39/29/2015-BRNS/39009), Govt. of India.
Subjects: Cerium oxide, Fabrication, Materials science, Polymer nanocomposite, Surface engineering, Refractive index, Nanoparticle, Nanotechnology, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, General Materials Science, Thin film, Physical and Theoretical Chemistry, Polystyrene, Polymer nanocomposites, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, chemistry, 0210 nano-technology
Abstract: Polymer nanocomposites have gained much importance in the field of optoelectronics due to their unique optical properties. Refractive index engineering using nanoparticles is an effective strategy that could be applied for the fabrication of optical devices. Herein, we report three different strategies which are employed to enhance the refractive index of polymer thin films. These include incorporating cerium oxide nanoparticles onto the polystyrene matrix, secondly adding cerium oxide nanoparticles onto the cross-linkable polystyrene and thirdly by embedding functionalized cerium oxide nanoparticles onto the cross-linkable polystyrene. Refractive index of the polystyrene thin films was enhanced by dispersing neat CeO 2 nanoparticles and functionalized CeO 2 nanoparticles into the polystyrene matrix. 1.38% enhancement in the refractive index of the polymer nanocomposite thin films could be achieved using our technique. The blending of polystyrene with cerium oxide nanoparticle presents a prospective way to engineer the refractive index of polymer thin films. We firmly believe that the study will be an effective guide towards future research in the area of surface engineering of polymer thin films for refractive index enhancement.
Published: 2019
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3. Benzene ring containing cationic gemini surfactants: Synthesis, surface properties and antibacterial activity

Author: Nadjia Benhamed, Mustapha Mohamed-Benkada, Yves Grohens, Khadidja Taleb, Salima Saidi-Besbes, Aicha Derdour, Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université des sciences et de la Technologie d'Oran Mohamed Boudiaf [Oran] (USTO MB), Institut de Recherche Dupuy de Lôme (IRDL), Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Centre National de la Recherche Scientifique (CNRS), and Laboratoire de Synthèse Organique Appliquée (LSOA)
Subjects: Aggregates, 02 engineering and technology, Antimicrobial activity, 010402 general chemistry, 01 natural sciences, Micelle, Surface tension, chemistry.chemical_compound, [SPI]Engineering Sciences [physics], Dynamic light scattering, Surface-active properties, Polymer chemistry, Materials Chemistry, Organic chemistry, Molecule, Physical and Theoretical Chemistry, Benzene, Gemini surfactant, Spectroscopy, Alkyl, chemistry.chemical_classification, Chemistry, Cationic polymerization, 021001 nanoscience & nanotechnology, Condensed Matter Physics, Atomic and Molecular Physics, and Optics, 0104 chemical sciences, Electronic, Optical and Magnetic Materials, Quaternary ammonium salt, 0210 nano-technology, Antibacterial activity
Abstract: International audience; New quaternary ammonium gemini surfactants of the general formula CnH2n+1-Ph-NHCOCH2N+(CH3)(2)-(CH2)(s)- N+(CH3)(2)CH2CONH-Ph-CnH2n+1 (with n = 8, 10,12, 14,16 and s = 2,4, 6) have been synthesized by an efficient synthetic pathway based on the quaternization of N,N,N',N'-tetramethylalkylenediamine with 2-bromo-N-(4-(alkyloxy) phenyl) acetamides. Their surface properties were investigated by surface tension, electrical conductivity and dynamic light scattering (DLS) measurements. The study shows that the incorporation of a benzene ring in the hydrophobic tail prompts micelle formation which leads to a smaller cmc values in the range of 0.21-0.009 mM compared to analogous geminis bearing alkyl hydrophobic chains. The length of the spacer and the hydrophobic chain has a pronounced effect on the aggregation behavior of surfactants molecules. This was confirmed by the average surfaces occupied by these molecules at the water-air interface calculated from the Gibbs equation. The size of the aggregates was measured by employing dynamic light scattering technique. The antimicrobial activity of investigated surfactants was evaluated against three microorganisms: Staphylococcus aureus, Escherichia coli and Candida albicans. (C) 2017 Elsevier B.V. All rights reserved.
Published: 2017
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4. Synthesis of N-pyridyl azoles using a deprotometalation-iodolysis-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

Author: Hedidi, Madani, Maillard, Julien, Erb, William, Lassagne, Frédéric, Halauko, Yury, Ivashkevich, Oleg, Matulis, Vadim, Roisnel, Thierry, Dorcet, Vincent, Hamzé, Monzer, Fajloun, Ziad, Baratte, Blandine, Ruchaud, Sandrine, Bach, Stéphane, Bentabed-Ababsa, Ghenia, Mongin, Florence, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université Libanaise, Biochimie - Ingénierie des protéines, Université de la Méditerranée - Aix-Marseille 2-Centre National de la Recherche Scientifique (CNRS), Phophorylation de protéines et Pathologies Humaines (P3H), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Fédération de recherche de Roscoff (FR2424), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Biologie Intégrative des Modèles Marins (LBI2M), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Plate-forme de criblage d'inhibiteurs de protéines kinases=Kinase Inhibitor Specialized Screening facility (KISSf), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS)-Station biologique de Roscoff (SBR), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Laboratoire de Synthèse Organique Appliquée, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), We acknowledge FEDER founds (D8 VENTURE Bruker AXS diffractometer) and Thermo Fisher (generous gift of 2,2,6,6-tetramethylpiperidine). L.P. and V.T. thank the French Cancer League (Comité 17) for financial support and the Cancéropôle Grand Ouest (axis: natural sea products in cancer treatment) for scientific support. S.B. and S.R. also thank the Cancéropôle Grand Ouest (axis: natural sea products in cancer treatment), IBiSA (French Infrastructures en sciences du vivant: biologie, santé et agronomie) and Biogenouest (Western France life science and environment core facility network) for supporting KISSf screening facility. This research has been partly performed as part of the CNRS PICS project ‘Bimetallic synergy for the functionalization of heteroaromatics’., LIttoral ENvironnement et Sociétés (LIENSs), and La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Stereochemistry, Pyridine, [SDV]Life Sciences [q-bio], chemistry.chemical_element, Antiproliferative activity, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, Iodine, 01 natural sciences, Biochemistry, Medicinal chemistry, Catalysis, Partial charge, chemistry.chemical_compound, Drug Discovery, ComputingMilieux_MISCELLANEOUS, Pyrrole, chemistry.chemical_classification, 010405 organic chemistry, Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Copper, 0104 chemical sciences, Pyridine Azole N-Arylation Copper Antiproliferative activity, N-Arylation, Proton NMR, Azole
Abstract: International audience; N-Arylation of pyrrole with 3-iodo-4-methoxypyridine was investigated by copper catalysis under different conditions. The best conditions, that proved to be protocol A (CuI, DMEDA or TMEDA, K 3 PO 4 , DMF at 110 C) and above all protocol B (Cu 2 O, Cs 2 CO 3 , DMSO at 110 C), were applied to the synthesis of various N-(methoxypyridyl) pyrroles, indoles and benzimidazoles. The behavior of the different iodinated methoxypyridines was rationalized by evaluating the partial positive charge on the carbon bearing iodine from the 1 H NMR chemical shift of the corresponding deiodinated substrates. The reaction was next connected with the deprotometalation-iodolysis step generating iodinated methoxypyridines: straight involvement of the crude iodo intermediates in pyrrole N-arylation afforded the expected N-(methoxypyridyl) pyrroles in good yields. Several synthesized N-(methoxypyridyl) azoles exerted low to moderate antiproliferative activity in A2058 melanoma cells.
Published: 2016
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5. Functionalization of pyridyl ketones using deprotolithiation-in situ zincation

Author: Thierry Roisnel, Yury S. Halauko, William Erb, Ghenia Bentabed-Ababsa, Vadim E. Matulis, Oleg A. Ivashkevich, Florence Mongin, Madani Hedidi, Frédéric Lassagne, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], and Belarusian State University
Subjects: In situ, General Chemical Engineering, chemistry.chemical_element, polysubstituted aromatics, coupling reactions, 010402 general chemistry, Iodine, center-dot-licl, 01 natural sciences, Coupling reaction, chemistry.chemical_compound, deprotonative metalation, Organic chemistry, [CHIM]Chemical Sciences, carbon bond formation, directed lithiation, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Aryl, Regioselectivity, heteroarenes, [CHIM.CATA]Chemical Sciences/Catalysis, General Chemistry, 0104 chemical sciences, chemistry, regioselectivity, pyridines, Surface modification, ch acidity relationships
Abstract: International audience; The metallation of aryl ketones was achieved by using LiTMP in the presence of ZnCl2 center dot TMEDA, as evidenced by subsequent interception with iodine or by a palladium-catalysed cross-coupling reaction. One of the synthesized iodo ketones has been further elaborated to reach derivatives of biological interest.
Published: 2016
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6. Iodothiophenes and Related Compounds as Coupling Partners in Copper-Mediated N-Arylation of Anilines

Author: Thierry Roisnel, Ghenia Bentabed-Ababsa, Valérie Thiéry, Vincent Dorcet, Salima Bouarfa, Laurent Picot, Florence Mongin, William Erb, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), European Regional Development Fund (Fonds Europeen de Developpement Regional, FEDER) European Union (EU), La Ligue contre le Cancer (French Cancer League), La Ligue contre le Cancer (Comite 17), La Ligue contre le Cancer (Comite 86), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés (LIENSs), and La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)
Subjects: antiproliferative activity, thiophene, chemistry.chemical_element, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, 010402 general chemistry, Iodine, 01 natural sciences, Medicinal chemistry, Catalysis, Potassium carbonate, chemistry.chemical_compound, Electrophilic substitution, Aniline, Thiophene, [CHIM]Chemical Sciences, Reactivity (chemistry), aniline, 010405 organic chemistry, iodine, [CHIM.ORGA]Chemical Sciences/Organic chemistry, N-arylation, Organic Chemistry, Copper, 0104 chemical sciences, Dibutyl ether, chemistry, copper, melanoma cells
Abstract: N-Arylation of various 2-acylated anilines with different electron-rich heteroaryl iodides (2- and 3-iodothiophenes, 2- and 3-iodobenzothiophenes, 2-iodobenzofuran) was achieved by using activated copper and potassium carbonate in dibutyl ether at reflux. The reactivity of the different heteroaryl iodides and anilines employed was discussed and rationalized on the basis of their electronic features. Subsequent cyclization by aromatic electrophilic substitution easily took place in the case of C2-free (benzo)thienyl or C3-free (benzo)furyl derivatives, affording original tri- and tetracycles. The antiproliferative activity of most of them was evaluated in A2058 melanoma cells and revealed four chlorinated tetracycles as effective growth inhibitors.
Published: 2021
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7. Enantioselective deprotometalation of alkyl ferrocenecarboxylates using bimetallic bases

Author: Floris Chevallier, Philippe C. Gros, Marielle Blot, Vincent Dorcet, William Erb, Ghenia Bentabed-Ababsa, Florence Mongin, Madani Hedidi, Dayaker Gandrath, Göran Hilmersson, Thierry Roisnel, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Laboratoire Lorrain de Chimie Moléculaire (L2CM), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry and Molecular Biology [Gothenburg], University of Gothenburg (GU), Agence Nationale de la Recherche (ACTIVATE program) French National Research Agency (ANR), ANR-08-BLAN-0051,ACTIVATE,ACTIVATEd 'ate compounds(2008), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: chemistry.chemical_element, Zinc, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, chemistry.chemical_compound, Materials Chemistry, [CHIM]Chemical Sciences, Tetrahydrofuran, Alkyl, deprotometalation, chemistry.chemical_classification, chiral base, 010405 organic chemistry, zinc, Enantioselective synthesis, ferrocene, General Chemistry, Lithium diisopropylamide, 0104 chemical sciences, chemistry, lithium, Yield (chemistry), Lithium, ester, Enantiomer
Abstract: International audience; The enantioselective deprotometalation of alkyl ferrocenecarboxylates (FcCO(2)R) using mixed lithium-zinc or lithium-cadmium bases is described. By using FcCO(2)Me as the substrate, chiral lithium alkyl-amidozincates prepared from exo-(alpha R)- or endo-(alpha S)-N-(alpha-phenylethyl)bornylamine (H-exo-born-R or H-endo-born-S) were tested; the best results (27% yield and 62% ee in favor of the R-P enantiomer) were obtained by using Bu-2(endo-born-S)ZnLi in tetrahydrofuran (THF) at -30 degrees C before iodolysis. Due to the low compatibility of FcCO(2)Me with alkyl-containing lithium zincates, 1 : 1 mixtures of lithium and zinc amides were tested. Chiral (H-exo-born-R or H-endo-born-S) or/and achiral (lithium 2,2,6,6-tetramethylpiperidide or lithium diisopropylamide) secondary amines gave good results, the best (81% yield and 44% ee in favor of the R-P enantiomer) being obtained by using (endo-born-S)(3)ZnLi in THF at room temperature. Among other secondary amines also prepared and/or tested, commercial (S,S)-bis(alpha-phenylethyl)amine (H-PEA-S) proved promising. After optimization of the reaction conditions, the best enantioselectivity (26% yield and 80% ee in favor of the RP enantiomer) was observed by treating a THF solution of FcCO(2)Me and Zn(PEA-S)(2) with Li-PEA-S at -80 degrees C before iodolysis. That no reaction took place with cadmium instead of zinc suggests the formation of 'ate complexes upon treatment of Cd(PEA-S)(2) by Li-PEA-S while Zn(PEA-S)(2) and Li-PEA-S would rather work in tandem (Li-PEA-S as the base and Zn(PEA-S)(2) as the in situ trap for the formed ferrocenyllithium). While FcCO(2)Me, FcCO(2)tBu and FcCO(2)iPr could be converted into their racemic 2-iodinated derivatives with a yield of 84 to 87% by employing LiTMP (2 equiv.) in the presence of ZnCl2.TMEDA (1 equiv.) as an in situ trap, their enantioselective deprotometalation rather required Li-PEA-S together with Zn(PEA-S)(2) to produce the enantio-enriched derivatives with yields of 45-82% and 71% ee.
Published: 2021
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8. A combined experimental and theoretical study of the thermal [3+2] cycloaddition of carbonyl ylides with activated alkenes

Author: Sandrine Ruchaud, Luis R. Domingo, Stéphane Fontanay, Raphaël E. Duval, Mar Ríos-Gutiérrez, Florence Mongin, Stéphane Bach, Thierry Roisnel, Stéphanie Philippot, Samira Hamza-Reguig, Ghenia Bentabed-Ababsa, Laboratoire de Synthèse Organique Appliquée, Universitat de València (UV), Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Laboratoire Lorrain de Chimie Moléculaire (L2CM), Phophorylation de protéines et Pathologies Humaines (P3H), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), CNRS, Centre National de la Recherche Scientifique, IUF, Institut Universitaire de France, 2016-78669, MINECO, Ministerio de Economía y Competitividad, Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Epoxide, 010402 general chemistry, enones, 01 natural sciences, Medicinal chemistry, Analytical Chemistry, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, [SDV.SP.MED]Life Sciences [q-bio]/Pharmaceutical sciences/Medication, Cascade reaction, [3+2] cycloaddition, Enamines, [CHIM]Chemical Sciences, Tetrahydrofurans, Spectroscopy, theoretical calculations, chemistry.chemical_classification, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Organic Chemistry, Regioselectivity, Cycloaddition, 0104 chemical sciences, carbonyl ylides, chemistry, Ylide, [SDV.MP.VIR]Life Sciences [q-bio]/Microbiology and Parasitology/Virology, Stereoselectivity, Cis–trans isomerism
Abstract: International audience; 4-Benzoyl-3,5-diaryltetrahydrofuran-2,2-dicarbonitriles were first synthesized from 2,2-dicyano-3-aryloxiranes and chalcones at toluene reflux; the 4,5-cis products proved to be predominantly formed and were isolated. Whereas shortened reaction times were observed by using microwave irradiation or catalytic cuprous chloride, no significant stereoselectivity change was in general noticed. Reacting 2,2-dicyano-3-aryloxiranes with 2-cyclopentenone next afforded 3-aryl-4-oxohexahydro-1H-cyclopenta[c]furan-1,1-dicarbonitriles, and the endo stereoisomers were isolated. That no stereoselectivity change was noticed in the presence of cuprous chloride rather suggests an impact of the salt on the epoxide ring opening. Finally, treatment of 2,2-dicyano-3-aryloxiranes by 2-morpholinoacrylonitrile yielded 3-cyano-3-morpholino-5-phenyltetrahydrofuran-2,2-dicarbonitriles from which the preponderant trans isomers were isolated. Importantly, the molecular mechanism of the domino reaction between 2,2-dicyano-3-phenyloxirane and 2-cyclopentenone was studied. The rate-determining thermal ring opening of the oxirane is followed by a non-concerted pseudoradical-type reaction of the carbonyl ylide with 2-cyclopentenone. Using the bond evolution theory also allowed the regioselectivity of this non-polar reaction to be explained.
Published: 2018
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9. In Situ ‘Trans-Metal Trapping’: An Efficient Way to Extend the Scope of Aromatic Deprotometalation

Author: Florence Mongin, Nahida Mokhtari Brikci-Nigassa, Ghenia Bentabed-Ababsa, William Erb, Laboratoire de Synthèse Organique Appliquée (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), PICS SYNAROM, Centre National de la Recherche Scientifique, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: In situ, Silicon, chemistry.chemical_element, in situ trap, Trapping, Zinc, 010402 general chemistry, Photochemistry, 01 natural sciences, Catalysis, Metal, Transmetalation, Gallium, deprotometalation, lithium amides, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, aromatic compounds, zinc, Organic Chemistry, silicon, 0104 chemical sciences, chemistry, transmetalation, visual_art, visual_art.visual_art_medium, Lithium, boron
Abstract: Deprotometalation is an efficient method to functionalize regioselectively aromatic compounds including heterocycles. This short review shows how it is possible to intercept aryllithiums (and other polar arylmetals) as soon as they are formed by in situ ‘trans-metal trapping’. The approach avoids long contact between aryllithiums and sensitive substrates. In addition, it allows less activated substrates to be deprotonated by non-nucleophilic lithium amides. While using chlorosilanes and borates still arouses the interest of chemists, more recently, methods based on zinc, aluminum and gallium have appeared, enabling this chemistry to grow dramatically.1 Introduction2 Silicon-Based In Situ Traps3 Boron-Based In Situ Traps4 Zinc-Based In Situ Traps5 Aluminum- and Gallium-Based In Situ Traps6 Other In Situ Traps7 Continuous-Flow In Situ ‘Trans-Metal Trapping’8 Conclusion
Published: 2018
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10. Crystal and molecular structure of (2Z,5Z)-3-(2-methoxyphenyl)-2-[(2-methoxyphenyl)imino]-5-(4-nitrobenzylidene)thiazolidin-4-one

Author: Ahmed Djafri, Abdelkader Chouaih, Jean-Claude Daran, Ayada Djafri, Fodil Hamzaoui, Laboratory of Technology and Properties of Solids, Abdelhamid Ibn Badis University, University Abd elhamid Ibn Badis of Mostaganem, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA)
Subjects: crystal structure, Stereochemistry, Imine, π–π interactions, Crystal structure, Dihedral angle, DFT calculations, 010402 general chemistry, 010403 inorganic & nuclear chemistry, Ring (chemistry), 01 natural sciences, Research Communications, Crystal, chemistry.chemical_compound, [pi]-[pi] interactions, Perpendicular, [CHIM.COOR]Chemical Sciences/Coordination chemistry, General Materials Science, thiazolidin-4-one, Crystallography, Chemistry, Hydrogen bond, thiazolidin-4-one, General Chemistry, hydrogen bonding, Condensed Matter Physics, 3. Good health, 0104 chemical sciences, QD901-999, π–π interactions, Nitro
Abstract: In the title molecule, both methoxyphenyl groups are nearly perpendicular to the thiazole ring and are nearly perpendicular to each other. In the crystal, a series of C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds, augmented by several C—H⋯π(ring) interactions, produce a three-dimensional architecture of molecules stacked along the b-axis direction., In the title compound, C24H19N3O5S, the thiazole ring (r.m.s. deviation = 0.012 Å) displays a planar geometry and is surrounded by three fragments, two methoxyphenyl and one nitrophenyl. The thiazole ring is almost in the same plane as the nitrophenyl ring, making a dihedral angle of 20.92 (6)°. The two methoxyphenyl groups are perpendicular to the thiazole ring [dihedral angles of 79.29 (6) and 71.31 (7)° and make a dihedral angle of 68.59 (7)°. The molecule exists in an Z,Z conformation with respect to the C=N imine bond. In the crystal, a series of C—H⋯N, C—H⋯O and C—H⋯S hydrogen bonds, augmented by several π–π(ring) interactions, produce a three-dimensional architecture of molecules stacked along the b-axis direction. The experimentally derived structure is compered with that calculated theoretically using DFT(B3YLP) methods.
Published: 2017
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11. Deprotometalation of substituted pyridines and regioselectivity-computed CH acidity relationships

Author: Florence Mongin, Floris Chevallier, Vincent Dorcet, Ghenia Bentabed-Ababsa, Aicha Derdour, Vadim E. Matulis, Thierry Roisnel, Yury S. Halauko, Madani Hedidi, Oleg A. Ivashkevich, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], UNESCO Chair of Belarusian State University, Minsk, Belarusian State University, This work was supported by the Ministère de l'Enseignement supérieur et de la Recherche scientifique Algérien (M.H.). F.M. thanks the Institut Universitaire de France and also Thermo Fisher for the generous gift of 2,2,6,6-tetramethylpiperidine. T.R. and V.D. thank FEDER founds (D8 VENTURE Bruker AXS diffractometer)., Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: pyridine, CH acidity, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Organic Chemistry, chemistry.chemical_element, Regioselectivity, 010402 general chemistry, Iodine, 01 natural sciences, Biochemistry, Medicinal chemistry, 3. Good health, 0104 chemical sciences, Gas phase, chemistry.chemical_compound, Drug Discovery, Pyridine, mixed lithium-zinc base, Organic chemistry, Surface modification, substituent effect, Tetrahydrofuran
Abstract: International audience; A series of methoxy- and fluoro-pyridines have been deprotometalated in tetrahydrofuran at room temperature by using a mixed lithium-zinc combination obtained from ZnCl2·TMEDA (TMEDA = N,N,N’,N’-tetramethylethylenediamine) and LiTMP (TMP = 2,2,6,6-tetramethylpiperidino) in a 1:3 ratio, and the metalated species intercepted by iodine. Efficient functionalization at the 3 position was observed from 4-methoxy, 2-methoxy, 2,6-dimethoxy, 2-fluoro and 2,6-difluoropyridine, and at the 4 position from 3-methoxy and 2,3-dimethoxypyridine. Interestingly, clean dideprotonation was noted from 3-fluoropyridine (at C2 and C4) and 2,6-difluoropyridine (at C3 and C5). The obtained regioselectivities have been discussed in light of the CH acidities of the substrates, determined both in the gas phase (DFT B3LYP and G3MP2B3 levels) and in THF solution. In the case of methoxypyridines, the pKa values have also been calculated for complexes with LiCl and LiTMP
Published: 2016
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12. Magnetic monolithic polymers prepared from high internal phase emulsions and Fe3O4 triazole-functionalized nanoparticles for Pb2+, Cu2+ and Zn2+ removal

Author: Noureddine Lebaz, Abdelhamid Elaissari, Zakaria Mokadem, Salima Saidi-Besbes, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Laboratoire d'automatique, de génie des procédés et de génie pharmaceutique (LAGEPP), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, Polymers and Plastics, General Chemical Engineering, Nanoparticle, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Biochemistry, [SPI.MAT]Engineering Sciences [physics]/Materials, Adsorption, Materials Chemistry, Environmental Chemistry, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, ComputingMilieux_MISCELLANEOUS, chemistry.chemical_classification, General Chemistry, Polymer, 021001 nanoscience & nanotechnology, Microstructure, 0104 chemical sciences, Template, Polymerization, Chemical engineering, chemistry, Emulsion, 0210 nano-technology, Porous medium
Abstract: A series of magnetic interconnected microcellular poly(styrene-DVB) polymeric monoliths were prepared by the polymerization of high internal phase emulsion (HIPE) templates then used as adsorbents to remove Pb2+, Cu2+ and Zn2+ ions from wastewaters. Magnetic Fe3O4 nanoparticles functionalized with 1,2,3-triazole cycle (MNP-Trz) were used to stabilize the emulsions and to impart magnetic properties and additional chelating sites to the porous materials. Important variations in microstructure were achieved by adjusting the concentration of MNP-Trz nanoparticles. The effects of external adsorption conditions including pH, initial concentration and contact time on the adsorption properties were systematically investigated. It was demonstrated that the adsorption equilibrium can be rapidly reached within 25 min for Cu2+ and Zn2+ and 40 min for Pb2+ with high maximal adsorption capacities of 303.3, 149.2 and 135.9 mg.g−1 for Pb2+, Cu2+ and Zn2+ respectively at pH = 5.5 and T = 25 °C. The easy and versatile preparation and excellent performance make these magnetic porous polymers excellent candidates for metal remediation.
Published: 2020
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13. Enantioselective deprotometalation of N,N-dialkyl ferrocenecarboxamides using metal amides

Author: Florence Mongin, Floris Chevallier, Masanobu Uchiyama, Madani Hedidi, Mutsumi Kimura, Tatsuya Yoshii, Philippe C. Gros, Yu Kitazawa, William Erb, Gandrath Dayaker, Ghenia Bentabed-Ababsa, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Shinshu University [Nagano], The University of Tokyo (UTokyo), RIKEN - Institute of Physical and Chemical Research [Japon] (RIKEN), Laboratoire Lorrain de Chimie Moléculaire (L2CM), Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique, Université de Rennes 1, Institut Universitaire de France, Agence Nationale de la Recherche, Ministère de l'Enseignement Supérieur et de la Recherche Scientifique, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Metal amides, chiral bases, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, DFT, Catalysis, chemistry.chemical_compound, Deprotonation, Amide, Materials Chemistry, Butyllithium, [CHIM.COOR]Chemical Sciences/Coordination chemistry, deprotometalation, Lithium amide, [CHIM.ORGA]Chemical Sciences/Organic chemistry, zinc, Enantioselective synthesis, General Chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Enantiopure drug, chemistry, lithium, ferrocene carboxamide, Enantiomer, 0210 nano-technology
Abstract: International audience; N,N-Diisopropylferrocenecarboxamide can be enantioselectively deprotometalated by combining butyllithium with (‒)-sparteine in diethyl ether at low temperature. It is of interest to identify conditions that could allow substrates bearing more reactive functional groups (such as esters and ketones) to be similarly converted. We here report our efforts to use different chiral lithium-zinc bases, made from a simple chiral lithium amide, (R,R)- or (S,S)-lithium bis(1-phenylethyl)amide (PEALi), for the enantioselective deprotonation of N,N-diisopropylferrocenecarboxamide. First, different zinc-based in situ traps were employed to intercept the formed ferrocenyllithium; optimization using enantiopure lithium bis[1-(S)-phenylethyl]amide ((S)-PEALi) led to the 2-iodo derivative in 96% yield and 69% ee in favor of the RP enantiomer. The method was extended to N,N-dimethylferrocenecarboxamide, morpholinoferrocenecarboxamide and N,N-diethylferrocenecarboxamide; for the latter, similar yield and enantioselectivity were recorded. DFT calculations on a model reaction showed very small differences between the activation energies leading to (RP)- and (SP)-2-lithioferrocenecarboxamides.Next, the behavior of various mixed amino-alkyl lithium zincates of the types R2[(S)-PEA]ZnLi and R2[(S)-PEA]2ZnLi2 (R = alkyl) was studied, notably by varying the reaction temperature and time, and the amount of base. The best results were obtained with Me2[(S)-PEA]2ZnLi2, affording the 2-iodo derivative in 97% yield and 86% ee in favor of the SP enantiomer.
Published: 2019
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14. Preparation and Characterization of Poly(methyl methacrylate) Particles by Combined Dispersion and Emulsion Polymerization

Author: Ibrahim H. A. Badr, Salima Saidi-Besbes, Chariya Kaewsaneha, Abdelhamid Elaissari, Hadjira Lahmar, Department of Chemistry, Mahidol University (Department of Chemistry, Mahidol University), Mahidol University [Bangkok], Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, Polymers and Plastics, General Chemical Engineering, Emulsion polymerization, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Materials Chemistry, medicine, [CHIM]Chemical Sciences, Methyl methacrylate, ComputingMilieux_MISCELLANEOUS, Dispersion polymerization, Polyvinylpyrrolidone, Organic Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 021001 nanoscience & nanotechnology, Poly(methyl methacrylate), 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, Chemical engineering, Polymerization, chemistry, visual_art, visual_art.visual_art_medium, Particle size, 0210 nano-technology, Dispersion (chemistry), medicine.drug
Abstract: Monodispersed poly(methyl methacrylate) (PMMA) nanoparticles were synthesized by combined dispersion and emulsion polymerization, using aqueous alcohol (methanol/water) as the dispersion medium. The influence of the dispersion medium ratio, stabilizer concentration, and initiator type and concentration on the colloidal stability, particle size, size distribution, and %conversion, was investigated. Submicron PMMA particles with a size of approximately 760 nm with a narrow size distribution, high conversion (91%) and good stability throughout the polymerization were obtained using a 50/50 methanol/water ratio, 1 wt% 2,2’-azobisisobutyronitrile (based on monomer), and 1 wt% polyvinylpyrrolidone (based on medium). With increasing the polarity of the dispersion medium (30/70 methanol/water ratio), the size and conversion of PMMA particles decreased to 345 nm and 72%, respectively.
Published: 2018
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15. Extending motifs in lithiocuprate chemistry: unexpected structural diversity in thiocyanate complexes

Author: Ghenia Bentabed-Ababsa, Thierry Roisnel, Andrew J. Peel, Florence Mongin, Madani Hedidi, Andrew E. H. Wheatley, University of Cambridge [UK] (CAM), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], EP/J500380/1, Engineering and Physical Sciences Research Council, Peel, Andrew [0000-0003-4690-5019], Wheatley, Andrew [0000-0002-2624-6063], Apollo - University of Cambridge Repository, Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: 0306 Physical Chemistry (incl. Structural), Thiocyanate, 010405 organic chemistry, Chemistry, Ligand, Nuclear magnetic resonance spectroscopy, Tetrahydropyran, 010402 general chemistry, Alkali metal, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, Inorganic Chemistry, chemistry.chemical_compound, Crystallography, Amide, 0302 Inorganic Chemistry, [CHIM]Chemical Sciences, Lewis acids and bases, Conformational isomerism
Abstract: The new area of lithio(thiocyanato)cuprates has been developed. Using inexpensive, stable and safe CuSCN for their preparation, these complexes revealed Lipshutz-type dimeric motifs with solvent-dependent point group identities; planar, boat-shaped and chair shaped conformers are seen in the solid state. In solution, both Lipshutz-type and Gilman structures are clearly seen. Since the advent in 2007 of directed ortho cupration, effort has gone into understanding the structure-reactivity effects of amide ligand variation in and alkali metal salt abstraction from Lipshutz-type cuprates such as (TMP)2Cu(CN)Li2(THF) 1 (TMP = 2,2,6,6-tetramethylpiperidide). The replacement of CN(-) with SCN(-) is investigated presently as a means of improving the safety of lithium cuprates. The synthesis and solid state structural characterization of reference cuprate (TMP)2Cu(CN)Li2(THP) 8 (THP = tetrahydropyran) precedes that of the thiocyanate series (TMP)2Cu(SCN)Li2(L) (L = OEt29, THF 10, THP 11). For each of 9-11, preformed TMPLi was combined with CuSCN (2 : 1) in the presence of sub-stoichiometric Lewis base (0.5 eq. wrt Li). The avoidance of Lewis basic solvents incurs formation of the unsolvated Gilman cuprate (TMP)2CuLi 12, whilst multidimensional NMR spectroscopy has evidenced the abstraction of LiSCN from 9-11 in hydrocarbon solution and the in situ formation of Gilman reagents. The synthetic utility of 10 is established in the selective deprotometalation of chloropyridine substrates, including effecting transition metal-free homocoupling in 51-69% yield.
Published: 2016
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16. Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

Author: Mohamed Yacine Ameur Ameur Messaoud, Ghenia Bentabed-Ababsa, Floris Chevallier, Aicha Derdour, Laurent Picot, Florence Mongin, Vincent Dorcet, Yury S. Halauko, Vadim E. Matulis, Thierry Roisnel, Oleg A. Ivashkevich, Valérie Thiéry, Madani Hedidi, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], UNESCO Chair of Belarusian State University, Minsk, Research Institute for Physico-Chemical Problems, Belarusian State University, LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés (LIENSs), and La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Base (chemistry), Heteroatom, Substituent, chemistry.chemical_element, Zinc, Medicinal chemistry, Full Research Paper, lcsh:QD241-441, chemistry.chemical_compound, lcsh:Organic chemistry, pyrroles, [CHIM]Chemical Sciences, Organic chemistry, lcsh:Science, iodolysis, Indole test, chemistry.chemical_classification, CH acidity, Organic Chemistry, Regioselectivity, mixed lithium–zinc bases, indoles, Hexane, Chemistry, chemistry, lcsh:Q, Lithium
Abstract: The synthesis of N-arylated pyrroles and indoles is documented, as well as their functionalization by deprotonative metallation using the base in situ prepared from LiTMP and ZnCl2·TMEDA (1/3 equiv). With N-phenylpyrrole and -indole, the reactions were carried out in hexane containing TMEDA which regioselectively afforded the 2-iodo derivatives after subsequent iodolysis. With pyrroles and indoles bearing N-substituents such as 2-thienyl, 3-pyridyl, 4-methoxyphenyl and 4-bromophenyl, the reactions all took place on the substituent, at the position either adjacent to the heteroatom (S, N) or ortho to the heteroatom-containing substituent (OMe, Br). The CH acidities of the substrates were determined in THF solution using the DFT B3LYP method in order to rationalize the experimental results.
Published: 2015
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17. Gemini surfactant modified clays Effect of surfactant loading and spacer length

Author: Isabelle Pillin, Yves Grohens, Salima Saidi-Besbes, Khadidja Taleb, Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Institut de Recherche Dupuy de Lôme (IRDL), Université de Bretagne Sud (UBS)-Université de Brest (UBO)-École Nationale Supérieure de Techniques Avancées Bretagne (ENSTA Bretagne)-Centre National de la Recherche Scientifique (CNRS), and Ministry of Higher Education and Scientific Research of Algeria [571/PNE/Doctorant/France/2016-2017]
Subjects: Thermogravimetric analysis, Ammonium bromide, Materials science, Scanning electron microscope, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Pulmonary surfactant, Geochemistry and Petrology, [CHIM]Chemical Sciences, Thermal stability, Fourier transform infrared spectroscopy, Ion exchange, Geology, [CHIM.MATE]Chemical Sciences/Material chemistry, 021001 nanoscience & nanotechnology, 0104 chemical sciences, Gemini surfactants, chemistry, Chemical engineering, Transmission electron microscopy, Organo modification, Arrangement, 0210 nano-technology
Abstract: Aromatic-containing gemini ammonium bromide surfactants with different spacer length and variable amounts were used to modify Na+-montmorillonite via ion exchange reaction. The resulting organoclays (OMt) were characterized in terms of composition and morphology using Fourier transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and X-ray diffraction (XRD). The thermal stability of OMt was determined by thermogravimetric analysis (TGA). The results indicated that gemini surfactants exhibit a good efficiency to modify clay mineral. Surfactant concentration and the length of the spacer connecting the ammonium heads were found to be key parameters governing the thermal stability and the structure of the corresponding OMt. Increasing surfactant concentration and lengthening of the spacer act favorably for the achievement of higher expended interlayer clay structures with better thermal stability. Different configurations of surfactant molecules within Mt interlayers were proposed based on d(001) basal spacing.
Published: 2018
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18. [1,2,3]-triazole derivatives: Mesomorphic property dependence on the molecular shape

Author: Eric Grelet, Ahmed Bentaleb, Salima Saidi-Besbes, Souria Benallou, Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Centre de recherches Paul Pascal (CRPP), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 1,2,3-Triazole, Materials science, 02 engineering and technology, 01 natural sciences, Thermotropic crystal, chemistry.chemical_compound, 3-dipolar cycloaddition, smectic mesophases, 3-triazole, General Materials Science, [PHYS]Physics [physics], 010405 organic chemistry, Liquid crystalline, Mesogen, General Chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, X-ray diffraction, Crystallography, Molecular geometry, chemistry, X-ray crystallography, catalyzed 1, 0210 nano-technology
Abstract: International audience; Nowadays, heterocyclic units have been extensively studied for the preparation of thermotropic liquid crystals due to their ability to impartlateral and/or longitudinal dipoles and induce changes in molecular shape. Key parameters to accede to stable mesophases are the positionof the heterocycle and the nature of terminal and linking functions. We present in this paper, an overview of several series of 1,2,3-triazole liquidcrystalline derivatives thatwe designed and characterized.We highlight the effect of different connecting functions and the geometry of mesogeniccore on the mesomorphic behavior of these derivatives.
Published: 2017
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19. Characterization of l-Theanine Excitatory Actions on Hippocampal Neurons: Toward the Generation of Novel N-Methyl-d-aspartate Receptor Modulators Based on Its Backbone

Author: Michel Vignes, Adrien Tassou, Fatiha Sebih, Mohammed Abouazza, Valérie Rolland, Janique Guiramand, Pierre Charnet, Thierry Cens, Gérard Barbanel, Céline Meusnier, Salima Bellahouel, Matthieu Rousset, Marc Rolland, Marie Celeste de Jesus Ferreira, Catherine Cohen-Solal, Maud Gratuze, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Centre de recherche en Biologie Cellulaire (CRBM), Université Montpellier 2 - Sciences et Techniques (UM2)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), and Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 0301 basic medicine, Physiology, [SDV.NEU.NB]Life Sciences [q-bio]/Neurons and Cognition [q-bio.NC]/Neurobiology, Xenopus, [CHIM.THER]Chemical Sciences/Medicinal Chemistry, Hippocampal formation, Biochemistry, Hippocampus, Membrane Potentials, Rats, Sprague-Dawley, Mice, 0302 clinical medicine, Glutamates, Excitatory Amino Acid Agonists, Receptor, Long-term depression, Cells, Cultured, gamma-Aminobutyric Acid, chemistry.chemical_classification, Neurons, Glutamate receptor, General Medicine, Amino acid, Excitatory postsynaptic potential, NMDA receptor, Agonist, medicine.drug_class, Cognitive Neuroscience, hippocampal neurons, Glutamic Acid, L-γ-N-propyl-glutamine, Biology, intracellular Ca 2+ homeostasis, NMDA receptors, Receptors, N-Methyl-D-Aspartate, microwave-assisted organic synthesis (MAOS), 03 medical and health sciences, L-Theanine, expression, medicine, Animals, Xenopus oocytes, Cell Biology, GluN2B, GluN2A, 030104 developmental biology, chemistry, Oocytes, Calcium, 030217 neurology & neurosurgery
Abstract: International audience; L-Theanine (or L-γ-N-ethyl-glutamine) is the major amino acid found in Camellia sinensis. It has received much attention because of its pleiotropic physiological and pharmacological activities leading to health benefits in humans, especially. We describe here a new, easy, efficient, and environmentally friendly chemical synthesis of L-theanine and L-γ-N-propyl-Gln and their corresponding D-isomers. L-Theanine, and its derivatives obtained so far, exhibited partial coagonistic action at N-methyl-D-aspartate (NMDA) receptors, with no detectable agonist effect at other glutamate receptors, on cultured hippocampal neurons. This activity was retained on NMDA receptors expressed in Xenopus oocytes. In addition, both GluN2A and GluN2B containing NMDA receptors were equally modulated by L-theanine. The stereochemical change from L-theanine to D-theanine along with the substitution of the ethyl for a propyl moiety in the γ-N position of Land D-theanine significantly enhanced the biological efficacy, as measured on cultured hippocampal neurons. L-Theanine structure thus represents an interesting backbone to develop novel NMDA receptor modulators.
Published: 2017
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20. Diastereospecific synthesis of new 4-substituted l-theanine derivatives

Author: Fatiha Sebih, Jean Martinez, Valérie Rolland, Salima Bellahouel, Aicha Derdour, Marc Rolland, Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Laboratoire de Synthèse Organique Appliquée (LSOA), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Erasmus Mundus Averroes program fellowship, and international convention between CNRS and Algerian'DGRFP
Subjects: Agonist, synthesis, Stereochemistry, medicine.drug_class, Alkylation, 010402 general chemistry, NMDA receptors, 01 natural sciences, Catalysis, Inorganic Chemistry, chemistry.chemical_compound, Stereospecificity, synapse, pure 4-substituted, medicine, Physical and Theoretical Chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Chemistry, Diastereospecific, Organic Chemistry, Enantioselective synthesis, L-theanine, Biological activity, Theanine, 3. Good health, 0104 chemical sciences, derivatives, NMDA receptor, Glutamatergic synapse, glutamatergic, protected (S)-pyroglutamate
Abstract: International audience; Considering the biological activity of L-theanine as a potent agonist of NMDA receptors, impacting on glutamatergic synapse activity, we have developed an asymmetric synthesis of new enantiomerically pure 4-substituted L-theanine derivatives. The key step is a stereospecific alkylation on a previously synthesized and correctly protected (S)-pyroglutamate.
Published: 2014
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21. Synthesis and mesomorphic properties of novel [1,2,3]-triazole mesogenic based compounds

Author: Chahinez Benbayer, Abdel Mounaim Safer, Aicha Derdour, Eric Grelet, Salima Saidi-Besbes, Frédéric Guittard, Narimane Kheddam, Elisabeth Taffin de Givenchy, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Centre de recherches Paul Pascal (CRPP), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Polarized light microscopy, 1,2,3-Triazole, 010405 organic chemistry, Liquid crystalline, Chemistry, Mesogen, Organic Chemistry, Substituent, Mesogens, 010402 general chemistry, 3-Triazole, 01 natural sciences, DSC, 0104 chemical sciences, Analytical Chemistry, Inorganic Chemistry, 3-Dipolar cycloaddition, chemistry.chemical_compound, Smectic mesophases, Differential scanning calorimetry, Polymer chemistry, 1,3-Dipolar cycloaddition, Moiety, Spectroscopy
Abstract: 7 pages; International audience; A series of five-membered heterocyclic 1,2,3-triazole derivatives with different substituents in N1 position was synthesized. The heterocyclic moiety was connected through an ester function to a p-decyloxyphenyl or p-decyloxybiphenyl tails Polarized microscopy studies, X-ray scattering and differential scanning calorimetry (DSC) analysis revealed that the target compounds exhibit enantiotropic liquid crystalline properties. Their mesomorphic behavior is closely related to the nature of the substituent X present in N1 position of the heterocycle.
Published: 2013
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22. Fused Systems Based on 2-Aminopyrimidines: Synthesis Combining Deprotolithiation-in situ Zincation with N -Arylation Reactions and Biological Properties

Author: Hedidi, Madani, Maillard, Julien, Erb, William, Lassagne, Frédéric, Halauko, Yury, Ivashkevich, Oleg, Matulis, Vadim, Roisnel, Thierry, Dorcet, Vincent, Hamze, Monzer, Fajloun, Ziad, Baratte, Blandine, Ruchaud, Sandrine, Bach, Stéphane, Bentabed-Ababsa, Ghenia, Mongin, Florence, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Belarusian State University, Centre AZM pour la Recherche en Biotechnologie et ses Applications, Université Libanaise, Phophorylation de protéines et Pathologies Humaines (P3H), Station biologique de Roscoff [Roscoff] (SBR), Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Université Pierre et Marie Curie - Paris 6 (UPMC)-Centre National de la Recherche Scientifique (CNRS)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Centre National de la Recherche Scientifique, Institut Universitaire de France, Ministère de l'Enseignement Supérieur et de la recherche algérien, Rennes Métropole, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Station biologique de Roscoff (SBR), Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.THER]Chemical Sciences/Medicinal Chemistry
Abstract: International audience; Various aromatic ketones were first functionalized next to the carbonyl function by deprotolithiation in the presence of a zinc salt followed by iodolysis. The outcome of the reactions was analyzed, and in particular their regioselectivity in the light of the calculated pKa values. The various halogenated ketones were next involved in copper-catalyzed twofold C-N bond formation in order to obtain fused systems based on 2-aminopyrimidines. Besides potential antibacterial effect, reached 2-aminobenzothiopyrano[4,3,2-de]quinazoline proved to inhibit PIM1 (IC50: 0.61 μM) and CDK2/cyclin A (IC50: 2.0 μM) kinases.
Published: 2017
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23. Triazole containing magnetic core-silica shell nanoparticles for Pb2+, Cu2+ and Zn2+ removal

Author: Sofiane Mekki, Aicha Derdour, Zakaria Mokadem, Géraldine Agusti, Abdelhamid Elaissari, Salima Saidi-Besbes, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Sénia [Oran], Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Langmuir, Chemistry(all), Magnetic, Scanning electron microscope, General Chemical Engineering, Inorganic chemistry, 0211 other engineering and technologies, Nanoparticle, Infrared spectroscopy, 02 engineering and technology, lcsh:Chemistry, Adsorption, Desorption, [CHIM]Chemical Sciences, ComputingMilieux_MISCELLANEOUS, 021110 strategic, defence & security studies, Chemistry, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 021001 nanoscience & nanotechnology, Thermogravimetry, [CHIM.POLY]Chemical Sciences/Polymers, lcsh:QD1-999, Heavy metal ions, Chemical Engineering(all), Nanoparticles, Magnetic nanoparticles, Triazole, 0210 nano-technology
Abstract: The main goal of this work was to investigate the ability of 1,2,3-triazole functionalized magnetic nanoparticles (MNP-Trz) and silica coated MNP homologous (MNPS-Trz) for removal of heavy metal cations. Three steps for efficient synthetic pathway were used for chemical modification of magnetic core based on copper catalyzed 1,3-dipolar cycloaddition. The magnetic nanoparticles were characterized by using various techniques such as X-ray diffraction (WAXD), infrared spectroscopy (FTIR), thermogravimetry analysis (TGA), zeta potential analysis, transmission electron microscopy (TEM) and scanning electron microscopy (SEM). The adsorption of prepared nanosized magnetic nanoparticles toward Cu 2+ , Pb 2+ and Zn 2+ ions was examined as a function of various physical-chemistry conditions. Adsorption isotherms and kinetics were studied and discussed by considering various theoretical models. The equilibrium kinetics was found to be second order model irrespective of investigated system. The best corroborating model with the obtained experimental results was found to be Langmuir one with maximum adsorption capacities at pH 5.5 and 25 °C for Cu 2+ , Pb 2+ and Zn 2+ ions found to be 87.87, 167.78 and 51.20 mg g −1 , respectively. Similar high maximum uptake tendency was also obtained for magnetic core-silica shell nanoparticles. It is interesting to notice that the regeneration of the used MNP-Trz was successfully achieved by using 0.1 M HNO 3 since 88% desorption efficiency was reached.
Published: 2016
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24. Magnetic Nanoadsorbents for Metal Remediation

Author: Aicha Derdour, Zakaria Mokadem, Salima Sadi-Besbes, Abdelhamid Elaissari, Graldine Agusti, Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Materials science, Waste management, Environmental remediation, 010401 analytical chemistry, 02 engineering and technology, [CHIM.MATE]Chemical Sciences/Material chemistry, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 021001 nanoscience & nanotechnology, 01 natural sciences, 0104 chemical sciences, Metal, [CHIM.POLY]Chemical Sciences/Polymers, visual_art, visual_art.visual_art_medium, [CHIM]Chemical Sciences, 0210 nano-technology, ComputingMilieux_MISCELLANEOUS
Abstract: International audience
Published: 2016
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25. Novel phenyl(thio)ureas bearing (thio)oxothiazoline group as potential BACE-1 inhibitors: synthesis and biological evaluation

Author: Christian Roussel, Mohammed Amine Mehdid, Federico Andreoli, Jean Dessolin, Nicolas Vanthuyne, Jean-Louis Kraus, Abdallah Larbi Doukara, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Université d'Oran 1 Ahmed Ben Bella [Oran], Chimie et Biologie des Membranes et des Nanoobjets (CBMN), and Université de Bordeaux (UB)-École Nationale d'Ingénieurs des Travaux Agricoles - Bordeaux (ENITAB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Stereochemistry, Thio, Chemistry Techniques, Synthetic, 010402 general chemistry, 7. Clean energy, 01 natural sciences, chemistry.chemical_compound, Molecular recognition, Drug Discovery, Fluorescence Resonance Energy Transfer, Aspartic Acid Endopeptidases, Urea, [CHIM]Chemical Sciences, Enzyme Inhibitors, ComputingMilieux_MISCELLANEOUS, Pharmacology, chemistry.chemical_classification, biology, 010405 organic chemistry, Chemistry, Hydrogen bond, Thiourea, Active site, Hydrogen Bonding, General Medicine, 0104 chemical sciences, Molecular Docking Simulation, Förster resonance energy transfer, Enzyme, Organocatalysis, Mutation, biology.protein, Amyloid Precursor Protein Secretases, Baculoviridae
Abstract: We report the synthesis and the β-site amyloid precursor protein cleaving enzyme-1 inhibitory properties of novel phenyl(thio)ureas bearing 2-(thio)oxothiazoline derivatives. A library of analogues was prepared according to specific synthetic schemes and the inhibitory activity was monitored using a fluorescence resonance energy transfer assay. Several analogues show potent inhibitory activities ranging between 1 and 0.01 µM and the activity is related to the NH acidity of the (thio)urea motif. Our results illustrate once again the close relationship between molecular recognition, complexation of the active site in enzymatic system, and organocatalysis utilizing explicit hydrogen bonding.
Published: 2011
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26. Synthesis of New Anionic and Cationic Polymerizable Surfactants for Emulsion Polymerization of Styrene

Author: Jean-Pierre Valour, Salima Saidi-Besbes, Aicha Derdour, Abdelhamid Elaissari, Sofiane Mekki, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
Subjects: Polymers and Plastics, Organic Chemistry, Cationic polymerization, Emulsion polymerization, 02 engineering and technology, Potassium persulfate, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 010402 general chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Styrene, ACTI, chemistry.chemical_compound, chemistry, Polymer chemistry, Particle diameter, Materials Chemistry, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, 0210 nano-technology, Ionic polymerization, Isomerization, ComputingMilieux_MISCELLANEOUS
Abstract: New anionic and cationic maleic surfmers containing a benzyl or p-vinylbenzyl hydrophobic tail were prepared and characterized. The behaviour of benzyl maleate hemiester in the emulsion polymerization process of styrene has been studied in the presence of potassium persulfate as initiator. The effect of surfmer concentration on particle diameter was particularly investigated.
Published: 2010
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27. Crystal structure of (2Z, 5Z)-3-(4-methoxyphenyl)-2- (4-methoxyphenyl) imino -5- (E)-3-(2-nitrophenyl)allylidene - 1,3-thiazolidin-4-one

Author: Rachida Rahmani, Ahmed Djafri, Jean-Claude Daran, Ayada Djafri, Abdelkader Chouaih, Fodil Hamzaoui, Laboratory of Technology and Properties of Solids, Abdelhamid Ibn Badis University, University Abd elhamid Ibn Badis of Mostaganem, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA)
Subjects: crystal structure, Stereochemistry, Stacking, Crystal structure, Dihedral angle, 010402 general chemistry, 010403 inorganic & nuclear chemistry, Ring (chemistry), thiazolidinone, 01 natural sciences, Medicinal chemistry, Research Communications, lcsh:Chemistry, Crystal, chemistry.chemical_compound, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Benzene, Hydrogen bond, General Chemistry, Condensed Matter Physics, hydrogen bonding, thiazolidinone, 0104 chemical sciences, 3. Good health, lcsh:QD1-999, chemistry, Nitro, π–π stacking
Abstract: The thiazole ring of the title compound is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°., In the title compound, C26H21N3O5S, the thiazole ring is nearly planar with a maximum deviation of 0.017 (2) Å, and is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π interactions link the molecules into a three-dimensional supramolecular architecture. Aromatic π–π stacking is also observed between the parallel nitrobenzene rings of neighbouring molecules, the centroid-to-centroid distance being 3.5872 (15) Å.
Published: 2016
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28. Synthesis and mesomorphic behaviour of unsymmetrical tetracatenar [1,2,3]-triazole derivatives

Author: Eric Grelet, Aicha Derdour, Soraya Benallou, Géraldine Agusti, Ahmed Bentaleb, Salima Saidi-Besbes, Abdelhamid Elaissari, Laboratoire de Synthèse Organique Appliquée (LSOA), Centre de Recherche Paul Pascal (CRPP), Université de Bordeaux (UB)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), and Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
Subjects: Materials science, 1,2,3-Triazole, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Differential scanning calorimetry, Liquid crystal, Phase (matter), 3-triazole, [CHIM.CRIS]Chemical Sciences/Cristallography, Organic chemistry, General Materials Science, Lamellar structure, XRD 1, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Mesogen, Mesophase, lamellar crystal, General Chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, columnar mesophase, Tetracatenar mesogen, 0104 chemical sciences, Crystallography, chemistry, Alkoxy group, 0210 nano-technology
Abstract: International audience; New nonsymmetric four-chained and three-chained [1,2,3]-triazole derivatives were synthesised. Their phase behaviours were investigated by differential scanning calorimetry, polarised optical microscopy and X-ray diffraction analyses. The tetracatenar derivatives show a columnar mesophase and a lamellar crystalline phase. The effects of the length of the terminal alkoxy chain and the nature of the terminal group attached to the side phenyltriazole unit of the mesogenic core are discussed.
Published: 2016
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29. Synergistic effect of organoclay fillers based on fluorinated surfmers for preparation of polystyrene nanocomposites

Author: Aicha Derdour, Sonia Amigoni, Salima Saidi-Besbes, Chahinez Benbayer, Frédéric Guittard, Elisabeth Taffin de Givenchy, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Thermogravimetric analysis, Nanocomposite, Materials science, Polymers and Plastics, Radical polymerization, General Chemistry, [CHIM.MATE]Chemical Sciences/Material chemistry, Exfoliation joint, Surfaces, Coatings and Films, chemistry.chemical_compound, chemistry, Polymer chemistry, Materials Chemistry, Organoclay, Moiety, Thermal stability, Polystyrene
Abstract: Novel fluorinated reactive surfactants were used for the organic modification of monmorillonite clays. These organoclays were used for the preparation of polystyrene−clay nanocomposites by in-situ free radical polymerization. Reference systems based on hydrocarbon homologous surfmer and nonpolymerizable surfactants were also used to deduce the effect of the fluorine moiety and the polymerizable function on the morphology and thermal stability of the prepared nanocomposites. Different structural parameters of the surfactants were investigated and modulated for the clay modification including: the nature of surfactant (surfmer/classical surfactant, fluorinated, or hydrocarbonated), the length of the fluorinated chain as well as the length of the hydrocarbon spacers linking the ammonium head to the fluorine chain or the polymerizable acrylic function. Wide angle-X-ray scattering (WAXD), thermogravimetric analysis (TGA), and electronic microcopies (TEM and SEM) were used to establish a structure-morphology, thermal properties relationships, and to highlight the key parameters governing the exfoliation process. © 2015 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2015, 132, 42347.
Published: 2015
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30. Deprotometalation-iodolysis and computed CH acidity of 1,2,3- and 1,2,4-triazoles. Application to the synthesis of resveratrol analogues

Author: Stéphane Fontanay, Stéphanie Philippot, Yury S. Halauko, Ghenia Bentabed-Ababsa, Floris Chevallier, Oleg A. Ivashkevich, Elisabeth Nagaradja, Mathieu Scalabrini, Raphaël E. Duval, Thierry Roisnel, Vadim E. Matulis, Florence Mongin, Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Structure et Réactivité des Systèmes Moléculaires Complexes (SRSMC), Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), UNESCO Chair of Belarusian State University, Minsk, Belarusian State University, We gratefully acknowledge Région Bretagne for financial support to E.N. F.M. also thank the Institut Universitaire de France and Rennes Métropole for financial support., Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Institut de Chimie du CNRS (INC)-Université de Lorraine (UL)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Base (chemistry), Clinical Biochemistry, Molecular Conformation, Triazole, Pharmaceutical Science, Antineoplastic Agents, Microbial Sensitivity Tests, Antiproliferative activity, Resveratrol, Crystallography, X-Ray, Gram-Positive Bacteria, 010402 general chemistry, 01 natural sciences, Biochemistry, chemistry.chemical_compound, Suzuki reaction, [SDV.SP.MED]Life Sciences [q-bio]/Pharmaceutical sciences/Medication, Cell Line, Tumor, Gram-Negative Bacteria, Stilbenes, Drug Discovery, Humans, Phenyl group, Organic chemistry, [CHIM]Chemical Sciences, CH-acidity, Molecular Biology, Cell Proliferation, chemistry.chemical_classification, Deprotonative metalation, 010405 organic chemistry, Aryl, Organic Chemistry, Triazoles, Anti-Bacterial Agents, 0104 chemical sciences, [SDV.MP]Life Sciences [q-bio]/Microbiology and Parasitology, chemistry, Resveratrol analogue, Molecular Medicine, Antiproliferative effect, Antibacterial activity
Abstract: International audience; 1-Aryl- and 2-aryl-1,2,3-triazoles were synthesized by N-arylation of the corresponding azoles using aryl iodides. The deprotometalations of 1-phenyl-1,2,3-triazole and -1,2,4-triazole were performed using a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination and occurred at the most acidic site, affording by iodolysis the 5-substituted derivatives. Dideprotonation was noted from 1-(2-thienyl)-1,2,4-triazole by increasing the amount of base. From 2-phenyl-1,2,3-triazoles, and in particular from 2-(4-trifluoromethoxy)phenyl-1,2,3-triazole, reactions at the 4 position of the triazolyl, but also ortho to the triazolyl on the phenyl group, were observed. The results were analyzed with the help of the CH acidities of the substrates, determined in THF solution using the DFT B3LYP method. 4-Iodo-2-phenyl-1,2,3-triazole and 4-iodo-2-(2-iodophenyl)-1,2,3-triazole were next involved in Suzuki coupling reactions to furnish the corresponding 4-arylated and 4,2’-diarylated derivatives. When evaluated for biological activities, the latter (which are resveratrol analogues) showed moderate antibacterial activity and promising antiproliferative effect against MDA-MB-231 cell line.
Published: 2015
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31. Access to N-Thioalkenyl and N-(o-Thio)aryl-benzimidazol-2-ones by Ring Opening of Thiazolobenzimidazolium and Benzimidazobenzothiazolium Salts and C-O Bond Cleavage of an Alkoxide

Author: Radia Kaid-Slimane, Federico Andreoli, Fabien Coppola, Nicolas Vanthuyne, Christian Roussel, Daniel Farran, Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], and Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Molecular Structure, 010405 organic chemistry, Aryl, Organic Chemistry, Thio, Oxides, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Medicinal chemistry, 3. Good health, 0104 chemical sciences, Thiazoles, chemistry.chemical_compound, chemistry, Alkoxide, Rapid access, Organic chemistry, [CHIM]Chemical Sciences, Benzimidazoles, Salts, Bond cleavage
Abstract: International audience; We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C-O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient and rapid access to the privileged benzimidazol-2-one scaffold.
Published: 2015
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32. Catalytic behavior of surfactant-containing-MCM-41 mesoporous materials for cycloaddition of 4-nitrophenyl azide

Author: Aicha Derdour, Abdelkader Bengueddach, Sarah Zeghada, Rachida Hamacha, Florence Mongin, Bouhadjar Boukoussa, Ghenia Bentabed Ababsa, Université d'Oran, Mat Chem Lab, Oran Es Senia, Algeria, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Sodium aluminate, 010405 organic chemistry, Process Chemistry and Technology, Inorganic chemistry, chemistry.chemical_element, Catalyst re-use, Mesoporous silica, 010402 general chemistry, MCM-41, 01 natural sciences, Cycloaddition reaction, Catalysis, 0104 chemical sciences, Tetraethyl orthosilicate, chemistry.chemical_compound, chemistry, Surfactant, [CHIM]Chemical Sciences, Azide, Gallium, Mesoporous material, Triazoles synthesis
Abstract: International audience; Si-MCM-41, Ga-MCM-41 and Al-MCM-41 mesoporous catalysts (with Si/Al = 80 and Si/Ga = 80) were prepared by direct synthesis under hydrothermal crystallization method using sodium aluminate or gallium sulfate and tetraethyl orthosilicate (TEOS) as aluminum or gallium and silica sources, respectively. The structural features of the materials were determined by various physico-chemical techniques such as X-ray diffraction (XRD), nitrogen sorption at 77 K, Fourier transform infrared spectroscopy (FTIR), scanning and transmission electronic microscopy (SEM, TEM) and thermogravimetric analysis ATG. The catalytic activity of the calcined and as-synthesized catalyst was evaluated through the cycloaddition reaction of 4-nitrophenyl azide with activated alkenes at room temperature under liquid-phase conditions. High yields of 1,2,3-triazole were obtained. For comparison purpose, mixtures of homogeneous and heterogeneous catalyst Et3N/M-MCM-41 (M = Al or Ga) are also tested. The catalyst was used in five consecutive experiments without important loss of activity, confirming its stability. Finally, a new method for preparing triazoles in short reaction times was developed.
Published: 2015
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33. Copolymerization of novel reactive fluorinated acrylic monomers with styrene: reactivity ratio determination

Author: Aicha Derdour, Chahinez Benbayer, Sonia Amigoni, Frédéric Guittard, Salima Saidi-Besbes, Elisabeth Taffin de Givenchy, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Polymers and Plastics, chemistry.chemical_element, Nuclear magnetic resonance spectroscopy, [CHIM.MATE]Chemical Sciences/Material chemistry, Onium, Styrene, chemistry.chemical_compound, Colloid and Surface Chemistry, Monomer, chemistry, Intramolecular force, Polymer chemistry, Materials Chemistry, Copolymer, Fluorine, Reactivity (chemistry), Physical and Theoretical Chemistry
Abstract: International audience; The radical copolymn. of three polymerizable surfactants with styrene was investigated by NMR spectroscopy to assess their compns. The reactivity ratios of these monomers were calcd. according to the methods of Fineman-Ross and Kelen-Tuedos. Consequently, Q and e values were deduced by the Alfrey and Price method. The results indicated the pos. effect of the fluorine chain on the reactivity of monomers bearing a long spacer between the ammonium head and the acrylic function. These monomers exhibit high e values which are in favor of an intramol. conformation of the surfactant where the ester carbonyl function of the polymerizable group interacts with the onium nitrogen atom via a compact six-sided structure.
Published: 2014
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34. Synthesis of C,N'-linked bis-heterocycles using a deprotometalation-iodination-N-arylation sequence and evaluation of their antiproliferative activity in melanoma cells

Author: Thierry Roisnel, Ghenia Bentabed-Ababsa, Aicha Derdour, Floris Chevallier, Vincent Dorcet, Florence Mongin, Madani Hedidi, Laurent Picot, Valérie Thiéry, Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], LIttoral ENvironnement et Sociétés - UMRi 7266 (LIENSs), Université de La Rochelle (ULR)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), LIttoral ENvironnement et Sociétés (LIENSs), and La Rochelle Université (ULR)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Models, Molecular, antiproliferative activity, Benzimidazole, Clinical Biochemistry, Pharmaceutical Science, Antineoplastic Agents, Pyrazole, Biochemistry, Medicinal chemistry, chemistry.chemical_compound, Structure-Activity Relationship, deprotonative metalation, five-membered aromatic heterocycles, Heterocyclic Compounds, Cell Line, Tumor, Drug Discovery, melanoma, Organic chemistry, Humans, Benzofuran, Molecular Biology, Cell Proliferation, Indazole, Dose-Response Relationship, Drug, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, N-arylation, Organic Chemistry, Benzothiophene, Tetramethylethylenediamine, Benzoxazole, Iodides, Triazoles, chemistry, Benzothiazole, Molecular Medicine, Drug Screening Assays, Antitumor
Abstract: International audience; Benzothiophene, benzofuran, benzothiazole and benzoxazole were deprotometalated using the lithium-zinc combination prepared from ZnCl2*TMEDA (TMEDA = N,N,N',N'-tetramethylethylenediamine, 1 equiv) and lithium 2,2,6,6-tetramethylpiperidide (LiTMP, 3 equiv). Subsequent interception of the 2-metalated derivatives using iodine as electrophile led to the iodides in 81, 82, 67 and 42% yields, respectively. These yields are higher (10% more) than those obtained using ZnCl2*TMEDA (0.5 equiv) and LiTMP (1.5 equiv), except in the case of benzoxazole (10% less). The crude iodides were involved in the N-arylation of pyrrole, indole, carbazole, pyrazole, indazole, imidazole and benzimidazole in the presence of Cu (0.2 equiv) and Cs2CO3 (2 equiv), and using acetonitrile as solvent (no other ligand) to provide after 24 h reflux the expected N-arylated azoles in yields ranging from 33 to 81%. Using benzotriazole also led to N-arylation products, but in lower 34, 39, 36 and 6% yields, respectively. A further study with this azole evidenced the impact of 2,2,6,6-tetramethylpiperidine on the N-arylation yields. Most of the C,N'-linked bis-heterocycles thus synthesized (in particular those containing benzimidazole) induced a high growth inhibition of A2058 melanoma cells after a 72 h treatment at 10-5 M.
Published: 2014
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35. Fluorinated surfmers modified clays and their corresponding polystyrene nanocomposites: structure-properties relationship study

Author: Benbayer, Chahinez, Saïdi-Besbes, Salima, Taffin De Givenchy, Elisabeth, Amigoni, Sonia, Derdour, Aicha, Guittard, Frédéric, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: [CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract: International audience
Published: 2013

36. Metathetic sulfur transfer mediated by N-(2-aminophenyl)-4-methyl-thiazolin-2-thione derivatives. Part III: An alkylthiol- and thioacid-free route to diversely substituted S-alkyl thioesters

Author: Andrea Buettner, Christian Roussel, Michel Giorgi, Nicolas Vanthuyne, Johannes Niebler, Federico Andreoli, Ayada Djafri, Mohammed Amine Mehdid, Daniel Farran, Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Department of Chemistry and Pharmacy, Emil Fischer Center, University of Erlangen-Nuremberg - Schuhstr. 19, 91052 Erlangen DE, Friedrich-Alexander Universität Erlangen-Nürnberg (FAU), Spectropôle - Aix Marseille Université (AMU SPEC), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS), Université d'Oran 1 Ahmed Ben Bella [Oran], and Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, Base (chemistry), 010405 organic chemistry, Organic Chemistry, chemistry.chemical_element, Alkylation, 010402 general chemistry, 01 natural sciences, Biochemistry, Sulfur, Medicinal chemistry, 0104 chemical sciences, Thiocarboxylic acid, Catalysis, Acylation, Part iii, chemistry, Drug Discovery, Organic chemistry, [CHIM]Chemical Sciences, lipids (amino acids, peptides, and proteins), Alkyl, ComputingMilieux_MISCELLANEOUS
Abstract: A metal free synthesis of S-alkyl thioesters, which does not involve alkylthiol or thiocarboxylic acid as sulfur source is disclosed. The process involves first an acylation at the nitrogen of the readily available N(2-aminophenyl)-4-methyl-thiazolin-2-thione, second an alkylation at sulfur of the resulting amides and finally a base catalyzed metathetic reaction, which provides under very mild conditions and in high isolated yields the S-alkyl thioesters. An ion-pair intermediate (9-acyl-3-methyl[1,3]thiazolo[3,2-a][3,1] benzimidazol-9-ium alkylthiolate) accounts for the formation of mixed thioesters during cross-coupling experiments. S-Alkyl diversity is provided by the alkylating agent and the acyl diversity comes from the acylating agent, while the sulfur atom is provided by the heterocycle.
Published: 2013
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37. Investigation of structure-surface properties relationship of semi-fluorinated polymerizable cationic surfactants

Author: Sonia Amigoni, Elisabeth Taffin de Givenchy, Chahinez Benbayer, Frédéric Guittard, Aicha Derdour, Salima Saidi-Besbes, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: chemistry.chemical_classification, Chemistry, Cationic polymerization, 02 engineering and technology, [CHIM.MATE]Chemical Sciences/Material chemistry, 010402 general chemistry, 021001 nanoscience & nanotechnology, 01 natural sciences, Micelle, 0104 chemical sciences, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, Biomaterials, Surface tension, Colloid and Surface Chemistry, Hydrocarbon, Pulmonary surfactant, Dynamic light scattering, Polymer chemistry, Moiety, Fluorocarbon, 0210 nano-technology
Abstract: International audience; Novel hybrid hydrocarbon/fluorocarbon ammonium type surfactant monomers (surfmers) of the general formula RF (CH2)l N(CH3)2(CH2)m OCOCH = CH2 with (RF = C4F9, C6F13, C8F17, l = 4, 6, 11, and m = 2-11) were synthesized and characterized. They exhibit very low surface tension as well as low critical micellar concentrations down to 1.39 10 5 mol/L. Special attention was focused on the effect of the polymerizable moiety, the length of the hydrocarbon spacers, and the fluorinated chains on surface activities of the reactive surfactants as compared to hydrocarbon surfmer analogs. Results indicate that the acrylic function has a pronounced effect on increasing the hydrophobic micelle character. This was confirmed by surface tensions and average surfaces occupied by these molecules at the water-gas interface. The micellar sizes were investigated by dynamic light scattering.
Published: 2013
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38. Structure-property study of new [1,2,3]-triazole liquid crystalline derivatives

Author: Salima Saidi-Besbes, Chahinez Benbayer, Eric Grelet, Aicha Derdour, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Centre de recherches Paul Pascal (CRPP), and Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 1,2,3-Triazole, Materials science, Double bond, mesogen, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, chemistry.chemical_compound, Differential scanning calorimetry, Wittig, 3-dipolar cycloaddition, Liquid crystal, smectic mesophases, 3-triazole, Organic chemistry, General Materials Science, chemistry.chemical_classification, Mesogen, General Chemistry, 021001 nanoscience & nanotechnology, Condensed Matter Physics, 0104 chemical sciences, Crystallography, chemistry, 1,3-Dipolar cycloaddition, Wittig reaction, [PHYS.PHYS.PHYS-CHEM-PH]Physics [physics]/Physics [physics]/Chemical Physics [physics.chem-ph], 0210 nano-technology, Isomerization
Abstract: International audience; The synthesis of a new type of liquid crystalline compound derived from 1,2,3-triazole was achieved using Wittig reaction. Polarisedmicroscopy studies, X-ray scattering and differential scanning calorimetry analysis revealed that the target compounds exhibit enantiotropic liquid crystalline properties. Their mesomorphic behaviour is closely related to the nature of substituents in position N1 of the heterocycle, the length of the mesogenic core as well as the isomerisation nature (E/Z) of the double bond.
Published: 2013
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39. Nanocomposites based on clays and fluorinated surfactant monomers. Synthesis and properties

Author: Benbayer, Chahinez, Saïdi-Besbes, Salima, Taffin De Givenchy, Elisabeth, Amigoni, Sonia, Derdour, Aicha, Guittard, Frédéric, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: [CHIM.MATE]Chemical Sciences/Material chemistry
Published: 2012

40. Studies of properties of nanocomposites based on clay and semi-fluorinated surfactant (surfmers)

Author: Benbayer, Chahinez, Saïdi-Besbes, Salima, Taffin De Givenchy, Elisabeth, Amigoni, Sonia, Derdour, Aicha, Guittard, Frédéric, Surfaces & Interfaces, Laboratoire de physique de la matière condensée (LPMC), Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-Centre National de la Recherche Scientifique (CNRS)-Université Nice Sophia Antipolis (... - 2019) (UNS), COMUE Université Côte d'Azur (2015-2019) (COMUE UCA)-COMUE Université Côte d'Azur (2015-2019) (COMUE UCA), Laboratoire de Synthèse Organique Appliquée, and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: [CHIM.MATE]Chemical Sciences/Material chemistry, ComputingMilieux_MISCELLANEOUS
Abstract: International audience
Published: 2012

41. Experimental and theoretical study of the [3+2] cycloaddition of carbonyl ylides with alkynes

Author: Ghenia Bentabed-Ababsa, José A. Sáez, Ekhlass Nassar, Florence Mongin, Vincent Dorcet, Samira Hamza-Reguig, Aicha Derdour, Luis R. Domingo, Thierry Roisnel, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Departamento de Quimica Organica, Universitat de València (UV), Institut des Sciences Chimiques de Rennes (ISCR), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA), Department of Chemistry, Université Ain Shams, Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: chemistry.chemical_classification, 010405 organic chemistry, Methyl propiolate, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, chemistry.chemical_element, Regioselectivity, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Chloride, Medicinal chemistry, Cycloaddition, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Phenylacetylene, Ylide, medicine, Reactivity (chemistry), Physical and Theoretical Chemistry, Indium, medicine.drug
Abstract: [EN] The [3 + 2] cycloaddition reaction between carbonyl ylides generated from epoxides and alkynes (phenylacetylene, methyl propiolate, methyl but-2-ynoate and methyl 3-phenylpropiolate) to give substituted 2,5-dihydrofurans was investigated. The effect of indium(III) chloride on the outcome of the reaction was studied in the case of phenylacetylene and methyl propiolate. The thermal reaction between the carbonyl ylide coming from 2,2-dicyano-3-phenyloxirane and both methyl propiolate and methyl but-2-ynoate was theoretically investigated using DFT methods in order to explain the reactivity and regioselectivity observed., The authors thank Rennes Metropole and the Institut Universitaire de France for financial support to F. M. We are also grateful to the Spanish Government (project CTQ2009-11027/BQU).
Published: 2012
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42. A focus on the asymmetric synthesis of a novel threo-ß-benzyl-ß-hydroxy aspartate analogue

Author: Michel Vignes, Nicolas Vanthuyne, Valérie Rolland, Jean Martinez, Salima Bellahouel, Sofiane Mekki, Aicha Derdour, Marc Rolland, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut des Sciences Moléculaires de Marseille (ISM2), Aix Marseille Université (AMU)-Centre National de la Recherche Scientifique (CNRS)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC), Institut Européen des membranes (IEM), Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Centre National de la Recherche Scientifique (CNRS), Aix Marseille Université (AMU)-École Centrale de Marseille (ECM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Montpellier 2 - Sciences et Techniques (UM2)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: biology, 010405 organic chemistry, Excitatory amino-acid transporter, Chemistry, Stereochemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Enantioselective synthesis, Biological activity, 010402 general chemistry, 01 natural sciences, Catalysis, 0104 chemical sciences, Inorganic Chemistry, Glutamatergic, biology.protein, Stereoselectivity, Physical and Theoretical Chemistry
Abstract: International audience; Considering the biological activity of b-alkyl-b-hydroxyaspartate derivatives as potent blockers of glutamate transporters (EAATs) impacting on glutamatergic synapses activity, we have developed a concise, asymmetric synthesis of enantiomerically pure threo-b-benzyl-b-hydroxyaspartates. The key step is a regiospecific and stereoselective Sharpless asymmetric aminohydroxylation (SAA) on previously synthesized benzyl fumarate.
Published: 2012
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43. ortho-Lithium/magnesium carboxylate-driven aromatic nucleophilic substitution reactions on unprotected naphthoic acids

Author: Regadia Aissaoui, Olivier Duval, Ariane Coquel, Thi Thanh Hà Dao, Anne-Sophie Castanet, Aicha Derdour, Jean-Jacques Helesbeux, Arnaud Nourry, Jacques Mortier, Unité de chimie organique moléculaire et macromoléculaire (UCO2M), Le Mans Université (UM)-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Substances d'Origine Naturelle et Analogues Structuraux (SONAS), and Université d'Angers (UA)
Subjects: Carboxylic Acids, chemistry.chemical_element, Lithium, Naphthalenes, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, chemistry.chemical_compound, Nucleophilic aromatic substitution, Nucleophilic substitution, Organometallic Compounds, Organic chemistry, Magnesium, Carboxylate, ComputingMilieux_MISCELLANEOUS, Alkyl, chemistry.chemical_classification, Molecular Structure, [CHIM.ORGA]Chemical Sciences/Organic chemistry, 010405 organic chemistry, Aryl, Organic Chemistry, 0104 chemical sciences, chemistry, Reagent, Indicators and Reagents
Abstract: Substitution of an ortho-fluoro or methoxy group in 1- and 2-naphthoic acids furnishing substituted naphthoic acids occurs in good to excellent yields upon reaction with alkyl/vinyl/aryl organolithium and Grignard reagents, in the absence of a metal catalyst without the need to protect the carboxyl (CO(2)H) group. This novel nucleophilic aromatic substitution is presumed to proceed via a precoordination of the organometallic with the substrate, followed by an addition/elimination.
Published: 2011
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44. threo-Diethyl 2-ethyl-2-hydroxy-3-(4-methylbenzenesulfonamido)succinate

Author: Arie van der Lee, Valérie Rolland, Marc Rolland, Sofiane Mekki, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut Européen des membranes (IEM), and Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)
Subjects: Crystallography, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Dimer, General Chemistry, Ethyl ester, 010402 general chemistry, 010403 inorganic & nuclear chemistry, Condensed Matter Physics, Bioinformatics, Organic Papers, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, 3. Good health, chemistry.chemical_compound, chemistry, QD901-999, Methyl benzene, [CHIM.CRIS]Chemical Sciences/Cristallography, General Materials Science, Ethyl group
Abstract: International audience; The asymmetric unit of the title compound, C17H25NO7S, contains two independent molecules, which are enantiomers forming a hydrogen-bonded dimer associated with two R2 2(7) patterns. In each molecule, one ethyl group from the two available ethyl ester functional groups is disordered. In one molecule, the ethyl group of the ester function from an - carboxylic acid is positionally disordered over two sets of sites with occupancies of 0.66:0.34. In the second molecule, it is the ethyl group in the -ester function that is disordered over two sets of sites with occupancies of 0.58:0.42.
Published: 2011
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45. Concomitant polymorphism in stereoselective synthesis of a $\beta$-benzyl $\beta$-hydroxy aspartate analogue

Author: Mekki, Sofiane, Rolland, Valérie, Bellahouel, Salima, Van-Der-Lee, Arie, Rolland, Marc, Laboratoire de Synthèse Organique Appliquée [Oran] (LSOA), Institut des Biomolécules Max Mousseron [Pôle Chimie Balard] (IBMM), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM), Institut Européen des membranes (IEM), and Centre National de la Recherche Scientifique (CNRS)-Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC)-Université de Montpellier (UM)
Subjects: [CHIM.CRIS]Chemical Sciences/Cristallography, [PHYS.COND.CM-MS]Physics [physics]/Condensed Matter [cond-mat]/Materials Science [cond-mat.mtrl-sci]
Abstract: International audience; Two concomitant polymorphs, (I) and (II), of a beta-benzyl- beta-hydroxyaspartate analogue [systematic name: dibenzyl 2-benzyl-2-hydroxy-3-(4-methylphenylsulfonamido)succinate], C32H31NO7S, crystallize from a mixture of ethyl acetate and cyclohexane at ambient temperature. The structure of (I) has triclinic (P1) symmetry and that of (II) monoclinic (P21/c) symmetry. Both crystal structures are made up of a stacking of homochiral racemic dimers (2S,3S and 2R,3R) which are internally connected by a similar R2 2(9) hydrogen-bonding pattern consisting of intermolecular N--H...O and O--H... O hydrogen bonds. The centroid of the racemic dimer lies on an inversion centre. The main structural difference between the two polymorphs is the conformational orientation of two of the four aromatic rings present in the molecule. Polymorph (II) is found to be twinned by reticular merohedry with twin index 3 and twin fractions 0.854 (1) and 0.146 (1).
Published: 2011
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46. A combined experimental and theoretical study of the thermal cycloaddition of aryl azides with activated alkenes

Author: Ghenia Bentabed-Ababsa, Aicha Derdour, Thierry Roisnel, José A. Sáez, Safer Abdelmounim, Luis R. Domingo, Florence Mongin, Sarah Zeghada, Ekhlass Nassar, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Departamento de Quimica Organica, Universitat de València (UV), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Department of Chemistry, Université Ain Shams, the Spanish Government (project CTQ2009-11027/BQU), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Azides, Antifungal Agents, Antineoplastic Agents, Microbial Sensitivity Tests, Activation energy, Alkenes, 010402 general chemistry, Photochemistry, 01 natural sciences, Biochemistry, Structure-Activity Relationship, chemistry.chemical_compound, Cell Line, Tumor, Thermal, Humans, Physical and Theoretical Chemistry, Microwaves, Molecular Structure, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Aryl, Organic Chemistry, Temperature, Regioselectivity, Stereoisomerism, Triazoles, Enol, Combinatorial chemistry, Tautomer, Cycloaddition, Anti-Bacterial Agents, 0104 chemical sciences, [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry, chemistry, Cyclization, Quantum Theory, Degradation (geology), Drug Screening Assays, Antitumor
Abstract: International audience; Reactions were performed from aryl azides on the one hand, and activated alkenes coming from β-dicarbonyl compounds or malonodinitrile on the other hand, either with recourse to conventional heating or to microwave activation, to afford 1-aryl-1H-1,2,3-triazoles. The mechanism and the regioselectivity of the reactions involving β-dicarbonyl compounds have been theoretically studied using DFT methods at the B3LYP/6-31G* level: they are domino processes comprising a tautomeric equilibrium of the β-dicarbonyl compounds with their enol forms, a 1,3-dipolar cycloaddition of the enol forms with the aryl azides (high activation energy), and a dehydration process (lower activation energy). The effect of non-conventional activation methods on the degradation of 1,2,3-triazolines was next studied experimentally. Finally, some of the 1,2,3-triazoles such synthesized were evaluated for their bactericidal and cytotoxic activities.
Published: 2011
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47. Synthesis and electrochemical behavior of a model redox-active thiacalix[4]arene-tetrathiafulvalene assembly

Author: Zhen-Ning Yan, Marc Sallé, Bang-Tun Zhao, Zhen Zhou, Esmah Belhadj, Franck Le Derf, Zhengzhou University, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Sénia [Oran], MOLTECH-ANJOU (MOLTECH-ANJOU), Centre National de la Recherche Scientifique (CNRS)-Université d'Angers (UA), Laboratoire de Chimie, Ingénierie Moléculaire et Matériaux d'Angers (CIMMA), Chimie Organique et Bioorganique : Réactivité et Analyse (COBRA), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie Organique Fine (IRCOF), Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Normandie Université (NU)-Institut national des sciences appliquées Rouen Normandie (INSA Rouen Normandie), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS)-Université de Rouen Normandie (UNIROUEN), Normandie Université (NU)-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Centre National de la Recherche Scientifique (CNRS), MOLTECH-Anjou, and Université d'Angers (UA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, 010402 general chemistry, Electrochemistry, Photochemistry, 01 natural sciences, Biochemistry, Combinatorial chemistry, Redox, 0104 chemical sciences, chemistry.chemical_compound, Transition metal, chemistry, Ferrocene, Covalent bond, Drug Discovery, Moiety, Cyclic voltammetry, Tetrathiafulvalene, ComputingMilieux_MISCELLANEOUS
Abstract: Syntheses of the ﬁrst bisthiacalix[4]arenes systems bridged by a tetrathiafulvalene (TTF) framework havebeen carried out through triethyl phosphite-mediated dechalcogenation dimerization of the correspond-ing 1,3-dithiole-2-ones. The cyclic voltammograms of the resulting bisthiacalix[4]arenes tethered by anelectroactive TTF unit are provided, and exhibit an electrochemical response in the case of introduction ofAg + . 2010 Elsevier Ltd. All rights reserved. The study of redox-active molecular receptors capable of sens-ing charged or neutral substrates and reporting their presence bymeans of an electrochemical response is an area of intense currentinterest. 1 Such systems incorporate a redox center presenting anelectrochemically reversible behavior (e.g., ferrocene, viologen,quinone or a transition metal), which is covalently associated toa binding site. Due to remarkable electronic properties, the tetra-thiafulvalene moiety (TTF) has appeared as a key building-blockfor switchable process in various molecular and supramoleculararchitectures.
Published: 2010
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48. Novel polymerizable surfactants: synthesis and application in the emulsion polymerization of styrene

Author: Aicha Derdour, Sofiane Mekki, Salima Saidi-Besbes, Jean-Pierre Valour, Abdelhamid Elaissari, Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Sénia [Oran], Laboratoire d'automatique et de génie des procédés (LAGEP), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), and University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran]
Subjects: Polymers and Plastics, Bulk polymerization, Emulsion polymerization, macromolecular substances, 02 engineering and technology, 010402 general chemistry, 01 natural sciences, Chain-growth polymerization, Polymer chemistry, Materials Chemistry, [CHIM]Chemical Sciences, [SPI.GPROC]Engineering Sciences [physics]/Chemical and Process Engineering, ComputingMilieux_MISCELLANEOUS, Chemistry, ACL, technology, industry, and agriculture, Cationic polymerization, Chain transfer, [CHIM.MATE]Chemical Sciences/Material chemistry, [SDV.SP]Life Sciences [q-bio]/Pharmaceutical sciences, 021001 nanoscience & nanotechnology, 0104 chemical sciences, [CHIM.POLY]Chemical Sciences/Polymers, Polymerization, Precipitation polymerization, 0210 nano-technology, Ionic polymerization
Abstract: A series of anionic maleic surfactants were synthesized, and their chemical structures were characterized by NMR. The synthesized surfmers were then used in emulsion polymerization of styrene in the presence of potassium persulfate as an initiator. The polymerization kinetics were investigated, and the obtained latex particles were characterized in terms of particle size and size distribution. The results obtained were compared with the emulsion polymerization of styrene in the presence of an SDS surfactant. The influences of the nature and concentration of surfmers on polymerization conversion and particle size in particular were investigated and discussed. Novel anionic polymerizable surfactants were prepared by reacting maleic anhydride with different benzyl alcohols. These surfmers were evaluated in the emulsion polymerization of styrene in the presence of potassium persulfate as the initiator. Special attention was focused on the effect of the concentration of surfmers on the polymerization kinetic and the final particle size through polymerization conversion particle size and size distribution determination.
Published: 2010
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49. Direct metallation of thienopyrimidines using a mixed lithium-cadmium base and antitumor activity of functionalized derivatives

Author: Ekhlass Nassar, Katia Snégaroff, Sidaty Cheikh Sid Ely, Ghenia Bentabed-Ababsa, Aicha Derdour, Enrico Perspicace, Frédéric Lassagne, Stéphanie Hesse, Florence Mongin, Chimie et Photonique Moléculaires (CPM), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Ain Shams University (ASU), Laboratoire d'Ingéniérie Moléculaire et Biochimie Pharmacologique (LIMBP), Université Paul Verlaine - Metz (UPVM), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
Subjects: Base (chemistry), Halogenation, Stereochemistry, chemistry.chemical_element, Antineoplastic Agents, Lithium, 010402 general chemistry, 01 natural sciences, Biochemistry, Cell Line, Tumor, Humans, Physical and Theoretical Chemistry, CERVIX CARCINOMA, Antitumor activity, chemistry.chemical_classification, Cadmium, Cell Death, 010405 organic chemistry, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, Combinatorial chemistry, 3. Good health, 0104 chemical sciences, Pyrimidines, chemistry, Cell culture, Doxorubicin, Drug Screening Assays, Antitumor, Human breast
Abstract: International audience; A series of thieno[2,3-d]- and thieno[3,2-d]pyrimidines have been easily synthesized using as key step a deproto-cadmiation-trapping sequence. Some of the compounds thus synthesized were screened for anti-cancer (cytotoxic) activities, and (S)-2-(6-iodo-2-phenylthieno[2,3-d]pyrimidin- 4-ylamino)-3-phenylpropanoic acid proved to have a significant activity towards liver, human breast and cervix carcinoma cell lines.
Published: 2009
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50. Deprotonative Metalation of Functionalized Aromatics using Mixed Lithium-Cadmium, Lithium-Indium, and Lithium-Zinc Species

Author: Aicha Derdour, Masanobu Uchiyama, Katia Snégaroff, Florence Mongin, Mitsuhiro Yonehara, Jean‐Martial L'Helgoual'ch, Tan Tai Nguyen, Floris Chevallier, Ghenia Bentabed-Ababsa, Chimie et Photonique Moléculaires (CPM), Université de Rennes (UR)-Centre National de la Recherche Scientifique (CNRS), RIKEN - Institute of Physical and Chemical Research [Japon] (RIKEN), RIKEN Center for Brain Science [Wako] (RIKEN CBS), Laboratoire de Synthèse Organique Appliquée, University of Oran Es-Senia [Oran] | Université d'Oran Es-Senia [Oran], Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Centre National de la Recherche Scientifique (CNRS), Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Rennes 1 (UR1), Université de Rennes (UNIV-RENNES)-Université de Rennes (UNIV-RENNES)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), and Institut National des Sciences Appliquées (INSA)-Université de Rennes (UNIV-RENNES)-Institut National des Sciences Appliquées (INSA)
Subjects: Diazine, 010405 organic chemistry, Metalation, [CHIM.ORGA]Chemical Sciences/Organic chemistry, Organic Chemistry, chemistry.chemical_element, General Chemistry, Tetramethylethylenediamine, 010402 general chemistry, 01 natural sciences, Medicinal chemistry, Catalysis, 0104 chemical sciences, chemistry.chemical_compound, chemistry, Benzothiazole, Pyridine, Thiophene, Organic chemistry, Lithium, Tetrahydrofuran
Abstract: International audience; In situ mixtures of CdCl(2)TMEDA (0.5 equiv; TMEDA = N,N,N',N'-tetramethylethylenediamine) or InCl(3) (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, respectively) were compared with the previously described mixture of ZnCl(2)TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(tmp)(3)CdLi] proved to be the best base when used in tetrahydrofuran at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt(2), CO(2)Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Five-membered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature. The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.
Published: 2009
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