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12 results on '"Abdellah N'ait Ousidi"'

1. Investigating novel thiazolyl-indazole derivatives as scaffolds for SARS-CoV-2 MPro inhibitors

Author

Justin Airas, Catherine A. Bayas, Abdellah N'Ait Ousidi, Moulay Youssef Ait Itto, Aziz Auhmani, Mohamed Loubidi, M'hamed Esseffar, Julie A. Pollock, and Carol A. Parish

Subjects
SARS-CoV-2, Coronavirus, COVID-19, MPro, Protease, Substrate, Pharmacy and materia medica, RS1-441, Other systems of medicine, RZ201-999
Abstract

COVID-19 is a global pandemic caused by infection with the SARS-CoV-2 virus. Remdesivir, a SARS-CoV-2 RNA polymerase inhibitor, is the only drug to have received widespread approval for treatment of COVID-19. The SARS-CoV-2 main protease enzyme (MPro), essential for viral replication and transcription, remains an active target in the search for new treatments. In this study, the ability of novel thiazolyl-indazole derivatives to inhibit MPro is evaluated. These compounds were synthesized via the heterocyclization of phenacyl bromide with (R)-carvone, (R)-pulegone and (R)-menthone thiosemicarbazones. The binding affinity and binding interactions of each compound were evaluated through Schrödinger Glide docking, AMBER molecular dynamics simulations, and MM-GBSA free energy estimation, and these results were compared with similar calculations of MPro binding various 5-mer substrates (VKLQA, VKLQS, VKLQG) and a previously identified MPro tight-binder X77. From these simulations, we can see that binding is driven by residue specific interactions such as π-stacking with His41, and S/π interactions with Met49 and Met165. The compounds were also experimentally evaluated in a MPro biochemical assay and the most potent compound containing a phenylthiazole moiety inhibited protease activity with an IC50 of 92.9 ​μM. This suggests that the phenylthiazole scaffold is a promising candidate for the development of future MPro inhibitors.

Published
2022
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2. Crystal structure of dimethyl 2-((2Z,5Z)-5-(2-methoxy-2-oxoethylidene)-2-{(E)-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]hydrazinylidene}-4-oxothiazolidin-3-yl)fumarate

Author

Abdellah N'ait Ousidi, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Abdelwahed Auhmani, and Jean-Claude Daran

Subjects
crystal structure, heterocyclic compounds, thiazolidine derivatives, natural product, Crystallography, QD901-999
Abstract

The crystal structure and the conformation of the title compound, C22H27N3O7S, were determined from the synthetic pathway and by X-ray analysis. This compound is a new 4-thiazolidinone derivative prepared and isolated as pure product from thiosemicarbazone carvone. The molecule is built up from an oxothiazolidine ring tetrasubstituted by a methoxy–oxoethylidene, a maleate, an oxygen and a cyclohexylidene–hydrazone. The cyclohexylidene ring is statistically disordered over two positions, resulting in an inversion of configuration for the substituted carbon.

Published
2017
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3. Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]thiazol-4(5H)-one

Author

Abdellah N'ait Ousidi, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Jean-Claude Daran, and Auhmani Abdelwahed

Subjects
crystal structure, absolute structure, heterocyclic compounds, thiazolidinone, indazole, C—H...O hydrogen bonding, C—H...π interactions, Crystallography, QD901-999
Abstract

The title compound, C13H19N3OS, is a new thiazolidin-4-one derivative prepared and isolated as the pure (3aS,6R)-diastereisomer from (R)-thiosemicarbazone pulegone. It crystallized with two independent molecules (A and B) in the asymmetric unit. The compound is composed of a hexhydroindazole ring system (viz. a five-membered dihydropyrazole ring fused to a cyclohexyl ring) with a thiazole-4-one ring system attached to one of the pyrazole N atoms (at position 2). The overall geometry of the two molecules differs slightly, with the mean planes of the pyrazole and thiazole rings being inclined to one another by 10.4 (1)° in molecule A and 0.9 (1)° in molecule B. In the crystal, the A and B molecules are linked via C—H...O hydrogen bonds, forming slabs parallel to the ab plane. There are C—H...π interactions present within the layers, and between the layers, so forming a three-dimensional structure.

Published
2016
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4. (3aR,6R)-3,3,6-Trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazole-2-carbothioamide

Author

Abdellah N'Ait Ousidi, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Sylviane Chevreux, and Moha Berraho

Subjects
crystal structure, indazole, carbothioamide, thiosemicarbazide, N—H...N hydrogen bonds, N—H...S hydrogen bonds, Crystallography, QD901-999
Abstract

The title compound, C11H19N3S, was prepared by the reaction of (R)-pulegone with thiosemicarbazide in acidic medium, using ethanol as solvent. The molecule is built up from fused six and five-membered rings. The six-membered ring adopts a chair conformation, while the five-membered ring displays an envelope conformation with the dimethyl-substituted C atom as the flap. The dihedral angle between the mean planes of the two rings is 20.35 (6)°. In the crystal, molecules are linked by N—H...N and N—H...S hydrogen bonds into chains running parallel to [100].

Published
2016
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7. Electrochemical and theoretical studies of some monoterpenic thiazolidinones as corrosion inhibitors for steel in acidic media

Author

Aziz Auhmani, Abdellah N'ait Ousidi, Rachid Idouhli, Mohy Eddine Khadiri, My Youssef Ait Itto, A. Abouelfida, and Abdelaziz Benyaich

Subjects
Materials science, Hydrochloric acid, 030206 dentistry, 02 engineering and technology, Surfaces and Interfaces, General Chemistry, 021001 nanoscience & nanotechnology, Electrochemistry, Surfaces, Coatings and Films, Corrosion, 03 medical and health sciences, chemistry.chemical_compound, 0302 clinical medicine, Adsorption, chemistry, Mechanics of Materials, Materials Chemistry, 0210 nano-technology, Nuclear chemistry
Abstract

This work deals with the study of the inhibition activity of three thiazolidinones (prepared from monoterpenic ketones) on the deterioration of S300 steel in hydrochloric acid solution. The potenti...

Published
2020
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8. Cytotoxic and apoptotic effects of some (R)-carvone-isoxazoline derivatives on human fibrosarcoma and carcinoma cells: experimental evaluation for cytotoxicity, molecular docking and molecular dynamics studies

Author

Ali Oubella, Abdoullah Bimoussa, Said Byadi, Yassine Laamari, Mourad Fawzi, Abdellah N’ait ousidi, Domen Oblak, Aziz Auhmani, Abdelkhalek Riahi, Hamid Morjani, and My Youssef Ait Itto

Subjects
Structural Biology, General Medicine, Molecular Biology
Abstract

This study aimed to analyze the cytotoxic and apoptotic effects of isoxazoline derivatives with monoterpene scaffold

Published
2022

9. Investigating Novel Thiazolyl-Indazole Derivatives as Scaffolds for SARS-CoV-2 MPro Inhibitors

Author

Justin Airas, Catherine A. Bayas, Abdellah N'Ait Ousidi, Moulay Youssef Ait Itto, Aziz Auhmani, Mohamed Loubidi, M'hamed Esseffar, Julie A. Pollock, and Carol A. Parish

Subjects
chemistry.chemical_classification, Indazole, Protease, Chemistry, Drug discovery, Stereochemistry, Ligand binding assay, medicine.medical_treatment, Phenacyl bromide, chemistry.chemical_compound, Enzyme, Docking (molecular), RNA Polymerase Inhibitor, medicine
Abstract

COVID-19 is a global pandemic caused by infection with the SARS-CoV-2 virus. Remdesivir, a SARS-CoV-2 RNA polymerase inhibitor, is the only drug to have received widespread approval for treatment of COVID-19. The SARS-CoV-2 main protease enzyme (MPro), essential for viral replication and transcription, remains an active target in the search for new treatments. In this study, the ability of novel thiazolyl-indazole derivatives to inhibit MPro is evaluated. These compounds were synthesized via the heterocyclization of phenacyl bromide with (R)-carvone and (R)-pulegone thiosemicarbazones. The binding affinity and atomistic interactions of each compound were evaluated through Schrödinger Glide docking, AMBER molecular dynamics simulations, and MM-GBSA free energy estimation, and these results were compared with similar calculations of MPro binding various 5-mer substrates (VKLQA, VKLQS, VKLQG). From these simulations, we can see that binding is driven by residue specific interactions such as π-stacking with His41, and S/π interactions with Met49 and Met165. The compounds were also experimentally evaluated in a MPro biochemical assay and the most potent compound containing a phenylthiazole moiety inhibited protease activity with an IC50 of 92.9 µM. This suggests that the phenylthiazole scaffold is a promising candidate for the development of future MPro inhibitors.

Published
2021
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10. New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

Author

Abdellah N'ait Ousidi, Aziz Auhmani, Abdelwahed Auhmani, Moulay Youssef Ait Itto, Abdelkhalek Riahi, Anthony Robert, Jean Claude Daran, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), and 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)

Subjects
010405 organic chemistry, Hydrogen bond, Chemistry, Crystal structure, Absolute configuration, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, Crystallography, Synthesis, Thiazolidine derivatives, Materials Chemistry, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Monoterpenic compounds
Abstract

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N—H...O hydrogen bonds, building an R 2 2(8) graph-set motif.

Published
2018
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11. Crystal structure of dimethyl 2-((2 Z ,5 Z )-5-(2-methoxy-2-oxoethylidene)-2-{( E )-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]hydrazinylidene}-4-oxothiazolidin-3-yl)fumarate

Author

Abdelwahed Auhmani, Aziz Auhmani, Abdellah N'ait Ousidi, Jean-Claude Daran, Abdelkhalek Riahi, My Youssef Ait Itto, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), and 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)

Subjects
Stereochemistry, Hydrazone, Crystal structure, 010403 inorganic & nuclear chemistry, Ring (chemistry), 01 natural sciences, Natural product, Research Communications, lcsh:Chemistry, chemistry.chemical_compound, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, chemistry.chemical_classification, 010405 organic chemistry, General Chemistry, Meth, Condensed Matter Physics, 3. Good health, 0104 chemical sciences, Thiazolidine derivatives, chemistry, lcsh:QD1-999, thia­zolidine derivatives, Heterocyclic compounds, Derivative (chemistry)
Abstract

The crystal structure of the title compound, dimethyl 2-((2Z,5Z)-5-(2-meth­oxy-2-oxo­ethyl­idene)-2-{(E)-[2-methyl-5-(prop-1-en-2-yl)cyclo­hex-2-enyl­idene]hydrazinyl­idene}-4-oxo­thia­zolidin-3-yl)fumarate displays a conformational disorder which inverts the configuration of the chiral C atom within the cyclo­hexyl­idene ring., The crystal structure and the conformation of the title compound, C22H27N3O7S, were determined from the synthetic pathway and by X-ray analysis. This compound is a new 4-thia­zolidinone derivative prepared and isolated as pure product from thio­semicarbazone carvone. The mol­ecule is built up from an oxo­thia­zolidine ring tetra­substituted by a meth­oxy–oxo­ethyl­idene, a maleate, an oxygen and a cyclo­hexyl­idene–hydrazone. The cyclo­hexyl­idene ring is statistically disordered over two positions, resulting in an inversion of configuration for the substituted carbon.

Published
2017
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12. Crystal structure of 2-[(3aS,6R)-3,3,6-trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]thiazol-4(5H)-one

Author

Jean-Claude Daran, Abdellah N'ait Ousidi, Auhmani Abdelwahed, Aziz Auhmani, Abdelkhalek Riahi, My Youssef Ait Itto, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), 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), and 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)

Subjects
crystal structure, Stereochemistry, C—H⋯O hydrogen bonding, Crystal structure, Pyrazole, 010402 general chemistry, Ring (chemistry), C—H⋯π inter­actions, 01 natural sciences, thiazolidinone, Research Communications, Crystal, chemistry.chemical_compound, C—H...π interactions, heterocyclic compounds, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, C—H...O hydrogen bonding, Indazole, Crystallography, 010405 organic chemistry, Hydrogen bond, General Chemistry, Condensed Matter Physics, HEXA, thia­zolidinone, 3. Good health, 0104 chemical sciences, chemistry, QD901-999, indazole, absolute structure, Derivative (chemistry)
Abstract

The absolute structure of the title compound was determined from the synthetic pathway and by resonant scattering. The compound is a new thia­zolidin-4-one derivative, prepared from (R)-thio­semicarbazone pulegone, and was isolated on crystallization from ethanol as the pure (3aS,6R)-diastereisomer., The title compound, C13H19N3OS, is a new thia­zolidin-4-one derivative prepared and isolated as the pure (3aS,6R)-diastereisomer from (R)-thio­semicarbazone pulegone. It crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro­indazole ring system (viz. a five-membered di­hydro­pyrazole ring fused to a cyclo­hexyl ring) with a thia­zole-4-one ring system attached to one of the pyrazole N atoms (at position 2). The overall geometry of the two mol­ecules differs slightly, with the mean planes of the pyrazole and thia­zole rings being inclined to one another by 10.4 (1)° in mol­ecule A and 0.9 (1)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked via C—H⋯O hydrogen bonds, forming slabs parallel to the ab plane. There are C—H⋯π inter­actions present within the layers, and between the layers, so forming a three-dimensional structure.

Published
2016
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