71 results on '"Guo-Rong Chen"'
Search Results
2. Supramolecular Assembly of TPE-Based Glycoclusters with Dicyanomethylene-4H-pyran (DM) Fluorescent Probes Improve Their Properties for Peroxynitrite Sensing and Cell Imaging
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Guo-Rong Chen, Hai-Hao Han, Xiao-Peng He, Yi Zang, Lei Dong, Meng-Qi Fu, Lifang Liu, Sébastien Vidal, Jia Li, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), and Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
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Supramolecular chemistry ,010402 general chemistry ,01 natural sciences ,Catalysis ,Supramolecular assembly ,chemistry.chemical_compound ,Peroxynitrous Acid ,Stilbenes ,[CHIM]Chemical Sciences ,ComputingMilieux_MISCELLANEOUS ,Fluorescent Dyes ,Pyrans ,Quenching (fluorescence) ,010405 organic chemistry ,Organic Chemistry ,Optical Imaging ,General Chemistry ,Tetraphenylethylene ,Combinatorial chemistry ,Fluorescence ,0104 chemical sciences ,chemistry ,Pyran ,Self-assembly ,Glycoconjugates ,Peroxynitrite - Abstract
Two red-emitting dicyanomethylene-4H-pyran (DM) based fluorescent probes were designed and used for peroxynitrite (ONOO- ) detection. Nevertheless, the aggregation-caused quenching effect diminished the fluorescence and restricted their further applications. To overcome this problem, tetraphenylethylene (TPE) based glycoclusters were used to self-assemble with these DM probes to obtain supramolecular water-soluble glyco-dots. This self-assembly strategy enhanced the fluorescence intensity, leading to an enhanced selectivity and activity of the resulting glyco-dot comparing to DM probes alone in PBS buffer. The glyco-dots also exhibited better results during fluorescence sensing of intracellular ONOO- than the probes alone, thereby offering scope for the development of other similar supramolecular glyco-systems for chemical biological studies.
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- 2020
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3. Low-dimensional materials facilitate the conjugation between fluorogenic boronic acids and saccharides
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Tony D. James, Guo Rong Chen, Bi Ying Cai, Yu Fei Li, Jie Chen, Xiaolong Sun, Xiao-Peng He, Shi Guo, and Wen Wen Chen
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Detection limit ,Chemistry ,02 engineering and technology ,Carbon nanotube ,010402 general chemistry ,021001 nanoscience & nanotechnology ,01 natural sciences ,0104 chemical sciences ,law.invention ,law ,Materials Chemistry ,Organic chemistry ,General Materials Science ,0210 nano-technology - Abstract
Here we demonstrate that low-dimensional materials (LDMs) enhance the conjugation between fluorogenic boronic acids (BAs) and saccharides. Among the LDMs investigated, 1D carbon nanotubes significantly lower the limit of detection and enhance the binding of the BA with D-fructose.
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- 2017
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4. Enhanced, shortened and tunable emission in Eu3+ doped borosilicate glasses by Cu+ co-doping
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Yang Wang, Alessia Cemmi, Guo-Rong Chen, Stefania Baccaro, Ilaria Di Sarcina, Wang, Y., Di Sarcina, I., Cemmi, A., Baccaro, S., and Chen, G.
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Materials science ,Analytical chemistry ,chemistry.chemical_element ,02 engineering and technology ,010402 general chemistry ,medicine.disease_cause ,+ ,01 natural sciences ,Spectral line ,Ion ,Inorganic Chemistry ,medicine ,Electrical and Electronic Engineering ,Physical and Theoretical Chemistry ,Spectroscopy ,Cu ,Borosilicate glass ,3+ ,Organic Chemistry ,Doping ,021001 nanoscience & nanotechnology ,Emission intensity ,Copper ,Atomic and Molecular Physics, and Optics ,0104 chemical sciences ,Electronic, Optical and Magnetic Materials ,co-doping ,Microsecond ,Eu ,chemistry ,Energy transfer ,Fast and tunable emission ,0210 nano-technology ,Ultraviolet - Abstract
A series of Cu+/Eu3+ co-doped borosilicate glasses have been successfully prepared by melt-quenching method. As proved by transmission spectra, the copper ions are univalent in the investigated borosilicate glasses. Under ultraviolet (UV) excitation at 325 nm, the emission intensity of Eu3+ increased by nearly double due to a large overlapping between the Cu+ and Eu3+ emission peaks. The decreased excitation intensity in UV region and shortened emission lifetime of Cu+ in association with presence of Eu3+ ions consistently suggest an energy transfer process from Cu+ to Eu3+ ions. On the other hand, the partially allowed transition of Cu+ makes contribution to the red emission of Eu3+ at 611 nm in Cu+/Eu3+ co-doped samples, thus shortening the lifetime from the conventional millisecond (∼1.86 ms) to the microsecond (up to around 37 μs) regime. Besides, tunable light is realized by combining the blue-green emission from Cu+ ions with the orange-red one from Eu3+ ions. The light can be continuously tuned by changing the Cu+/Eu3+ concentration ratio, indicating that the present novel Cu+/Eu3+ co-doped borosilicate glasses are potential as fast response and tunable photoluminescence materials.
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- 2019
5. Thiophenol detection using an AIE fluorescent probe through self-assembly with TPE-based glycoclusters
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Xiao-Peng He, Guo-Rong Chen, Lei Dong, Sébastien Vidal, Chimie Organique 2-Glycochimie (CO2GLYCO), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), and East China University of Science and Technology
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Aqueous solution ,Thiophenol ,Organic Chemistry ,High selectivity ,Phosphate buffered saline ,02 engineering and technology ,010402 general chemistry ,021001 nanoscience & nanotechnology ,Photochemistry ,01 natural sciences ,Biochemistry ,Fluorescence ,6. Clean water ,0104 chemical sciences ,chemistry.chemical_compound ,Environmental water ,chemistry ,[CHIM.ANAL]Chemical Sciences/Analytical chemistry ,Self-assembly ,Physical and Theoretical Chemistry ,0210 nano-technology ,Sensing system - Abstract
International audience; We describe a novel green-emitting tetraphenylethylene-dicyanomethylene-4H-pyran (TPE-DCM) based fluorescent probe (TD-1). Conjugating TPE and DCM moieties allowed TD-1 to display high selectivity for thiophenol with excellent AIE properties in aqueous solution. Nevertheless, the poor water-solubility from the hydrophobic structure resulted in the weak and unstable emission intensity. Non-covalent self-assembly of TD-1 with TPE glycocluster (TPE2S) led to a largely improved water solubility producing a reliable and stable sensing system. The corresponding glyco-probe could detect sensitively exogenous thiophenol concentrations in PBS buffer or environmental water samples.
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- 2019
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6. Benzo[c]carbazole derivatives produced by an effective Diels–Alder reaction: synthesis and structure–activity-relationship for surface coating
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Guo-Rong Chen, Xue-Qing Feng, Xin-Yan Wu, Xiao-Peng He, Feng Sha, and Fei Zhang
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010405 organic chemistry ,Carbazole ,General Chemical Engineering ,General Chemistry ,010402 general chemistry ,01 natural sciences ,0104 chemical sciences ,Surface coating ,chemistry.chemical_compound ,chemistry ,Structure–activity relationship ,Organic chemistry ,Erosion corrosion of copper water tubes ,Diels–Alder reaction - Abstract
We demonstrate the use of an effective Diels–Alder reaction to produce a library of heterocyclic, polyaromatic benzo[c]carbazole derivatives with good corrosion inhibitive potency for copper against HCl.
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- 2016
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7. Fluorescence Imaging of Alzheimer's Disease with a Flat Ensemble Formed between a Quinoline-Malononitrile AIEgen and Thin-Layer Molybdenum Disulfide
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Wei-Tao Dou, Zhiqian Guo, Xiao-Peng He, Jing-Jing Zhang, Guo-Rong Chen, Qiang Li, Hai-Yan Zhang, and Weihong Zhu
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Male ,Fluorescence-lifetime imaging microscopy ,Thin layer ,Mice, Transgenic ,010402 general chemistry ,01 natural sciences ,Biochemistry ,chemistry.chemical_compound ,Alzheimer Disease ,Limit of Detection ,Animals ,Disulfides ,Molecular Biology ,Molybdenum disulfide ,Malononitrile ,Fluorescent Dyes ,Molybdenum ,Mice, Inbred ICR ,Amyloid beta-Peptides ,010405 organic chemistry ,Organic Chemistry ,Quinoline ,Optical Imaging ,Brain ,Fluorescence ,Peptide Fragments ,0104 chemical sciences ,chemistry ,Aqueous buffer ,Biophysics ,Quinolines ,Molecular Medicine ,Self-assembly - Abstract
The sensitive imaging of amyloid-β (Aβ) peptides is important for the timely detection of neurodegenerative diseases, such as Alzheimer's disease (AD). Although clinically the diagnosis of AD relies on the use of radiolabeled imaging reagents, herein we report the simple construction of a "flat ensemble" formed between a quinoline-malononitrile AIEgen (EDS) and thin-layer molybdenum disulfide (2D MoS2 ) for the sensitive detection of Aβ by means of fluorescence-based techniques. Self-assembly between EDS and 2D MoS2 in aqueous buffer solution produces the flat ensemble, and the subsequent interaction of the material ensemble with oligomeric and aggregated Aβ peptides leads to up to 19-fold enhanced fluorescence of EDS. The ensemble is also applicable for staining Aβ aggregates in vivo.
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- 2018
8. Direct Aldolization of Unprotected Fructose to Bio-Based Surfactants
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Guo-Rong Chen, Marc Lemaire, Biwen Zhu, Nicolas Duguet, Catalyse Synthèse et Environnement (CASYEN), Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS), East China University of Science and Technology, Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)-Université Claude Bernard Lyon 1 (UCBL), and Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut de Chimie du CNRS (INC)-École Supérieure Chimie Physique Électronique de Lyon-Centre National de la Recherche Scientifique (CNRS)
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chemistry.chemical_classification ,Hydrogen ,Base (chemistry) ,010405 organic chemistry ,Renewable Energy, Sustainability and the Environment ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,General Chemical Engineering ,Trimethylamine ,chemistry.chemical_element ,Bio based ,Fructose ,General Chemistry ,Alkylation ,010402 general chemistry ,01 natural sciences ,Tautomer ,0104 chemical sciences ,chemistry.chemical_compound ,chemistry ,Yield (chemistry) ,Environmental Chemistry ,Organic chemistry ,[CHIM]Chemical Sciences ,ComputingMilieux_MISCELLANEOUS - Abstract
A new alkylation mode of fructose was developed by direct aldolization of unprotected fructose with fatty aldehydes as alkylating agents. The reaction occurs in the presence of a base in a mixture of water/EtOH at 60 °C under microwave irradiation. Trimethylamine was found the most effective base for the aldolization of fructose with short chain aldehydes (C4–C8) while better results were obtained with K2CO3 in association with tetrabutylphosphonium bromide (TBPB) for long chain aldehydes (C8–C12). The corresponding alkylated fructose were obtained as mixture of 3 main tautomers (the β-pyranoid form being the predominant isomer) and were isolated with 31–46% yield. These aldolization products were also reduced under hydrogen to give the corresponding alkylated heptaols with 84–96% isolated yields.
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- 2018
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9. Triazole-Linked Glycolipids Enhance the Susceptibility of MRSA to β-Lactam Antibiotics
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Guo-Rong Chen, Daijie Chen, Xi-Le Hu, Xiao-Peng He, Li Dan, Lei Shao, and Dong Xiaojing
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biology ,Stereochemistry ,medicine.drug_class ,Organic Chemistry ,Antibiotics ,Triazole ,biochemical phenomena, metabolism, and nutrition ,biology.organism_classification ,Biochemistry ,Microbiology ,chemistry.chemical_compound ,Minimum inhibitory concentration ,Glycolipid ,chemistry ,Mechanism of action ,Drug Discovery ,Lactam ,medicine ,Click chemistry ,medicine.symptom ,Bacteria - Abstract
We show here that a series of triazolyl glycolipid derivatives modularly synthesized by a "click" reaction have the ability to increase the susceptibility of a drug-resistant bacterium to β-lactam antibiotics. We determine that the glycolipids can suppress the minimal inhibitory concentration of a number of ineffective β-lactams, upward of 256-fold, for methicillin-resistant Staphylococuss aureus (MRSA). The mechanism of action has been preliminarily probed and discussed.
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- 2015
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10. Mixed galactolipid anomers accentuate apoptosis of multiple myeloma cells by inducing DNA damage
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Guo-Rong Chen, Chao Zhang, Jia Li, Yi Zang, Sisi Deng, Huan Wang, and Xiao-Peng He
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Anomer ,Galactolipid ,Cell Survival ,DNA damage ,Antineoplastic Agents ,Apoptosis ,Cleavage (embryo) ,Biochemistry ,Analytical Chemistry ,chemistry.chemical_compound ,Cell Line, Tumor ,Humans ,Polymerase ,biology ,Galactolipids ,Organic Chemistry ,Drug Synergism ,General Medicine ,chemistry ,biology.protein ,Poly(ADP-ribose) Polymerases ,Growth inhibition ,Multiple Myeloma ,DNA Damage - Abstract
This study describes an interesting observation that the mixture of anomeric galactolipids has synergistic effects on the growth inhibition of human multiple myeloma (MM) cells. We determine that the equivalent mixture of a pair of α- and β-galactolipids with a 14-carbon lipid chain can cause stronger poly ADP-ribose polymerase cleavage and DNA damage, producing more late apoptotic MM cells, than either anomer alone.
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- 2015
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11. Solvent-Switched Benzylic Methylene Functionalization: Addition, Ring-Opening, Cyclization, and Unexpected Cleavage of C–O and C–C Bonds
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Guo Rong Chen, Deng Yuan Li, Xue Song Shang, and Pei Nian Liu
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Organic Chemistry ,Ring (chemistry) ,Biochemistry ,Enol ,Medicinal chemistry ,Catalysis ,Solvent ,chemistry.chemical_compound ,Elimination reaction ,chemistry ,Cascade reaction ,Yield (chemistry) ,Physical and Theoretical Chemistry ,Methylene - Abstract
Intermolecular benzylic methylene functionalization of exo-cyclic enol ethers has been achieved using imines as reagents and potassium tert-butoxide as the catalyst. Depending on the solvent used, the reaction proceeds by two pathways. In THF, an addition/elimination reaction of exo-cyclic enol ethers with imines provides dihydroisobenzofuran derivatives in good yield. In DMSO, an addition/ring-opening/cyclization cascade reaction occurs with unexpected cleavage of C-O and C-C bonds, affording isoquinolin-1(2H)-one products in high yield under ambient reaction conditions.
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- 2013
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12. Construction of triazolyl bidentate glycoligands (TBGs) by grafting of 3-azidocoumarin to epimeric pyranoglycosides via a fluorogenic dual click reaction
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Guo-Rong Chen, Kaixian Chen, Jia-Lu Xue, Jin-Wei Yang, Xiao-Peng He, Juan Xie, Chao-Ying Cheng, and De-Tai Shi
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chemistry.chemical_classification ,Azides ,Denticity ,Organic Chemistry ,Glycoside ,Stereoisomerism ,General Medicine ,Triazoles ,Ligands ,Biochemistry ,Galactoside ,Fluorescence ,Combinatorial chemistry ,Analytical Chemistry ,chemistry.chemical_compound ,chemistry ,Glucoside ,Coumarins ,3-Azidocoumarin ,Click chemistry ,Organic chemistry ,Click Chemistry ,Glycosides ,Lewis acids and bases ,Fluorescent Dyes - Abstract
Glycoligands, which feature a glycoside as the central template incorporating Lewis bases as metal chelation sites and various fluorophores as the chemical reporter, represent a range of interesting scaffolds for development of chemosensors. Here, new types of triazolyl bidentate glycoligands (TBGs) based on the grafting of 3-azidocoumarin to the C2,3- or C4,6-positions of three epimeric pyranoglycosides including a glucoside, a galactoside, and a mannoside were efficiently synthesized via a fluorogenic dual click reaction assisted by microwave irradiation. The desired TBGs were afforded in high conversion rates (>90%) and reasonable yields (∼70%). Moreover, a preliminary optical study of two hydroxyl-free glucoside-based TBGs indicates that these compounds are strongly fluorescent in pure water, implying their potential for ion detections in aqueous media.
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- 2012
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13. Identification of diverse 1,2,3-triazole-connected benzyl glycoside-serine/threonine conjugates as potent corrosion inhibitors for mild steel in HCl
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Xiao-Peng He, Liang Cai, Qiong Deng, Kaixian Chen, Xiao-Li Wei, Guo-Rong Chen, Yi-Tao Long, and Na-Na Ding
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chemistry.chemical_classification ,1,2,3-Triazole ,General Chemical Engineering ,Glycoside ,General Chemistry ,Galactoside ,Cycloaddition ,Corrosion ,Amino acid ,chemistry.chemical_compound ,chemistry ,Glucoside ,Organic chemistry ,General Materials Science ,Threonine - Abstract
The corrosion inhibitive efficiency of diverse 1,2,3-triazolyl benzyl glucoside-, galactoside- and mannoside-serine/threonine conjugates readily synthesized via Cu I -catalyzed azide–alkyne cycloaddition reaction (Cue-AAC) for mild steel in HCl was examined via electrochemical impedance spectroscopy. The results indicate that these compounds are potent corrosion inhibitors even in highly concentrated HCl solutions. The potential mechanism of three inhibitors was characterized in detail via polarization and isotherm calculations. This study implies that benzyl glycoside-amino acid hybrids effectively constructed via the Cue-AAC between the highly biocompatible sugars and amino acids may represent a new class of promising and potentially green corrosion inhibitors.
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- 2012
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14. Copper(II) triflate-catalyzed reduction of carboxylic acids to alcohols and reductive etherification of carbonyl compounds
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Yin-Jie Zhang, Wissam Dayoub, Guo-Rong Chen, and Marc Lemaire
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Reduction (complexity) ,chemistry.chemical_compound ,Primary (chemistry) ,Copper(II) triflate ,Chemistry ,Organic Chemistry ,Drug Discovery ,High selectivity ,Biochemistry ,Medicinal chemistry ,Catalysis - Abstract
A protocol is described for the reduction of carboxylic acids to primary alcohols using 1,1,3,3-tetramethyldisiloxane (TMDS) and a catalytic amount of Cu(OTf) 2 . Aliphatic as well as aromatic carboxylic acids are reduced in high selectivity and good yields. TMDS/Cu(OTf) 2 has also been found to be an efficient catalytic reducing system for the preparation of symmetrical ethers from carbonyl compounds under mild conditions.
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- 2012
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15. Research on the structure–surface adsorptive activity relationships of triazolyl glycolipid derivatives for mild steel in HCl
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Hai-Lin Zhang, Guo-Rong Chen, Xiao-Peng He, Qiong Deng, Yi-Tao Long, and Kaixian Chen
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Galactolipid ,Molecular Structure ,Surface Properties ,Organic Chemistry ,Disaccharide ,Alcohol ,General Medicine ,Biochemistry ,Catalysis ,Cycloaddition ,Analytical Chemistry ,Corrosion ,Dielectric spectroscopy ,chemistry.chemical_compound ,Adsorption ,Glycolipid ,chemistry ,Cyclization ,Steel ,Organic chemistry ,Hydrochloric Acid ,Glycolipids ,Copper - Abstract
Triazolyl glycolipid derivatives constructed via CuI-catalyzed azide-alkyne 1,3-dipolar cycloaddition reaction (Cue-AAC) represent a new range of carbohydrate-based scaffolds for use in many fields of the chemical research. Here the surface adsorptive ability of series of our previously prepared C1- or C6-triazole linked gluco- and galactolipid derivatives for mild steel in 1 M HCl was studied via electrochemical impedance spectroscopy (EIS). Results indicated that these monosaccharide–fatty acid conjugates are weak inhibitors against HCl corrosion for mild steel. Moreover, some newly synthesized triazolyl disaccharide (maltose)–fatty alcohol conjugates failed to display enhanced activity, meaning that the structural enlargement of the sugar moiety does not favor the iron surface adsorption. However, a bis-triazolyl glycolipid derivative, which was realized by introducing a benzenesulfonamide group via Cue-AAC to the C6-position of a C1-triazolyl glucolipid analog, eventually showed significantly improved adsorptive potency compared to that of its former counterparts. The corrosion inhibitive modality of this compound for mild steel in HCl was subsequently studied via potentiodynamic polarization and thermodynamic calculations.
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- 2012
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16. Concise CuI-Catalyzed Azide–Alkyne 1,3-Dipolar Cycloaddition Reaction Ligation Remarkably Enhances the Corrosion Inhibitive Potency of Natural Amino Acids for Mild Steel in HCl
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Bao-Qin Chen, Kaixian Chen, Hong-Wei Shi, Qiong Deng, Guixia Liu, Xiao-Peng He, Guo-Rong Chen, Yun Tang, and Yi-Tao Long
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chemistry.chemical_classification ,General Chemical Engineering ,Alkyne ,General Chemistry ,Industrial and Manufacturing Engineering ,Cycloaddition ,Catalysis ,Corrosion ,Amino acid ,chemistry.chemical_compound ,chemistry ,1,3-Dipolar cycloaddition ,Organic chemistry ,Azide ,Chemical ligation - Abstract
Despite natural amino acids having been proposed as the green surrogate of currently used corrosion inhibitors that are generally toxic to both nature and human body during the everyday industrial processing of metallic equipments, their structural simplicity yet lowers the inhibitive potency, thereby hampering their further industrialization. We disclose here that a concise chemical ligation (CuI-catalyzed azide–alkyne 1,3-dipolar cycloaddition reaction [Cue-AAC]) between two l-amino acids that are weak or noncorrosion inhibitors may result in their largely improved protective effect for mild steel in HCl. A series of 1,4-disubstituted 1,2,3-triazolyl bis-amino acid derivatives constituted by l-serine, l-threonine, l-phenylalanine, and l-tyrosine were efficiently synthesized via Cue-AAC and deprotection reactions in high yields. Subsequently performed electrochemical impedance spectroscopy (EIS) evidenced that the inhibitive effect of these compounds for mild steel in 1 M HCl is markedly better than that...
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- 2012
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17. Novel triazolyl bis-amino acid derivatives readily synthesized via click chemistry as potential corrosion inhibitors for mild steel in HCl
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Xiao-Peng He, Na-Na Ding, Bao-Qin Chen, Yi-Tao Long, Guixia Liu, Yun Tang, Hong-Wei Shi, Guo-Rong Chen, and Qiong Deng
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Chemistry ,General Chemical Engineering ,Triazole ,Hydrochloric acid ,General Chemistry ,Electrochemistry ,Combinatorial chemistry ,Dielectric spectroscopy ,Corrosion ,Metal ,chemistry.chemical_compound ,visual_art ,visual_art.visual_art_medium ,Click chemistry ,Gravimetric analysis ,Organic chemistry ,General Materials Science - Abstract
Triazolyl bis-amino acid derivatives readily synthesized via click chemistry were identified as novel potent corrosion inhibitors for mild steel in HCl. The inhibitive characteristic of compound 4 was studied in detail via gravimetric measurement, electrochemical impedance spectroscopy, potentiodynamic polarization and scanning electron microscopy. In addition, a quantum chemical study suggests that the triazole ring involved in these inhibitors is structurally essential for the protection of metal surface.
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- 2012
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18. TMDS as a Dual-Purpose Reductant in the Regioselective Ring Cleavage of Hexopyranosyl Acetals to Ethers
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Yin-Jie Zhang, Wissam Dayoub, Guo-Rong Chen, and Marc Lemaire
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Dual purpose ,Chemistry ,Organic Chemistry ,Regioselectivity ,Organic chemistry ,Physical and Theoretical Chemistry ,Cleavage (embryo) ,Ring (chemistry) ,Combinatorial chemistry - Abstract
1,1,3,3-Tetramethyldisiloxane (TMDS) has been developed as an excellent dual-purpose reductant for the highly regioselective ring cleavage of various hexopyranosyl 4,6-O-acetals with Cu(OTf)2 or AlCl3 to afford the corresponding primary and secondary ethers. Its application to the concise synthesis of carbohydrate-based surfactants is highlighted.
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- 2012
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19. Click to a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides: Novel construction of PTP1B inhibitors on a sugar scaffold
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Li-Xin Gao, Jia Li, Yin-Jie Zhang, Xiao-Xin Shi, Cui Li, Zhen Li, Yun Tang, Guo-Rong Chen, Xiao-Peng He, and Juan Xie
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Models, Molecular ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,Pharmacology ,chemistry.chemical_classification ,Spectrometry, Mass, Electrospray Ionization ,Magnetic Resonance Spectroscopy ,animal structures ,Glycoconjugate ,Stereochemistry ,Electrospray ionization ,Organic Chemistry ,Carbohydrates ,General Medicine ,Protein tyrosine phosphatase ,Nuclear magnetic resonance spectroscopy ,Benzoic Acid ,Glucosides ,chemistry ,Drug Discovery ,Click chemistry ,Enzyme Inhibitors ,Sugar ,Selectivity ,Alkyl - Abstract
With an aim of developing novel protein tyrosine phosphatase (PTP) 1B inhibitors based on sugar scaffolds, a focused library of benzyl 6-triazolo(hydroxy)benzoic glucosides was efficiently constructed via the modular and selective Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddtion (click chemistry). These glycoconjugates bearing alkyl chain length-varied bridges between the sugar and (hydroxy)-benzoic moieties were identified as new PTP1B inhibitors with selectivity over T-Cell PTP (TCPTP), SH2-Containing PTP-1 (SHP-1), SHP-2 and Leukocyte Antigen-Related Tyrosine Phosphatase (LAR). Molecular docking study sequentially elaborated the plausible binding modes of the structurally diverse sugar-based inhibitors with PTP1B.
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- 2011
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20. In situ spectroeletrochemistry and cytotoxic activities of natural ubiquinone analogues
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Da-Wei Li, Yi-Tao Long, Hong-Yuan Chen, Yi-Lun Ying, Wei Ma, Hao Zhou, and Guo-Rong Chen
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In situ ,Radical ,Organic Chemistry ,Biochemistry ,law.invention ,chemistry.chemical_compound ,chemistry ,Bromide ,law ,Drug Discovery ,Cytotoxic T cell ,Electron paramagnetic resonance ,Cytotoxicity ,Continuous exposure ,IC50 - Abstract
Quinones are a group of potent antineoplastic agents. Here we described effective and facile routes to synthesize a series of ubiquinone analogues (UQAs). These unique compounds have been investigated by electrochemistry and in situ UV–vis spectroelectrochemistry to explore their electron-transfer processes and radical properties in aprotic media. The structure–activities relationships of inhibiting cancer cell proliferation of UQAs were examined in murine melanoma B16F10 cells using a 72 h continuous exposure MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. Our results revealed that UQAs had improved antiproliferative activity and displayed better inhibitory effects than natural ubiquinone 10. The cytotoxic activities of UQAs were correlated to the semiubiquinone radicals, which were confirmed by in situ electron spin resonance (ESR). In the cytotoxicity test, 6-vinylubiquinone 5 and 6-(4′-fluorophenyl) ubiquinone 7 that possess half maximal inhibitory concentration value (IC50) of 6.1 μM and 6.2 μM. This would make them as valuable candidates for future pharmacological studies.
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- 2011
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21. 6-O-Amino-2-O-carboxymethyl Glucopyranoside as Novel Glycoaminoxy Acid Building Block for the Construction of Oligosaccharide Mimetics
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Juan Xie, Zhuo Song, Xiao-Peng He, and Guo-Rong Chen
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Chemistry ,Stereochemistry ,Block (telecommunications) ,Organic Chemistry ,Organic chemistry ,Catalysis - Published
- 2011
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22. Synthesis of novel 6-triazologlycolipids via click chemistry and their preliminary cytotoxicity assessments
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Wei Zhang, Hai-Lin Zhang, Xiao-Peng He, Xiao-Xin Shi, Guo-Rong Chen, Yuan Yao, Jia Li, and Li Sheng
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Glycosylation ,Stereochemistry ,Triazole ,Antineoplastic Agents ,Catalysis ,Inorganic Chemistry ,HeLa ,Structure-Activity Relationship ,chemistry.chemical_compound ,Cell Line, Tumor ,Drug Discovery ,Humans ,Moiety ,MTT assay ,Glycosyl ,Physical and Theoretical Chemistry ,Cytotoxicity ,Molecular Biology ,biology ,Organic Chemistry ,General Medicine ,Triazoles ,biology.organism_classification ,Cycloaddition ,chemistry ,Click chemistry ,Click Chemistry ,Drug Screening Assays, Antitumor ,Glycolipids ,Information Systems - Abstract
Series of novel 6-triazole-linked galacto- or glucolipids were efficiently synthesized from O-benzylated sugar azides and various lipid alkynes via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click chemistry) followed by hydrogenolysis with PdCl(2)/H(2). Subsequent MTT (3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay toward a panel of human cancer cell lines revealed that these triazologlycolipids possess low-to-modest toxicity on A549 (lung), MCF-7 (breast), HeLa (cervix), and HepG2 (liver). Furthermore, both the carbon chain length at the lipid end and the epimeric identity of the glycosyl moiety were determined to impact their corresponding bioactivity.
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- 2011
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23. Creation of 3,4-bis-triazolocoumarin–sugar conjugates via flourogenic dual click chemistry and their quenching specificity with silver(I) in aqueous media
- Author
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Guo-Rong Chen, Zhuo Song, Xiao-Peng He, Kaixian Chen, Zhi-Zhou Wang, and Xiao-Xin Shi
- Subjects
Aqueous solution ,Chemistry ,Metal ions in aqueous solution ,Organic Chemistry ,Biochemistry ,Fluorescence ,Galactoside ,chemistry.chemical_compound ,Drug Discovery ,Click chemistry ,Organic chemistry ,Epimer ,Azide ,Selectivity - Abstract
Fluorogenic click chemistry has recently emerged as an ingenious and powerful tool toward numerous biochemical purposes. We describe herein the use of dual click chemistry toward the fluorescence restoration of a fluorogenic coumarin on epimeric dipropargyl sugar scaffolds and their practical utility in selective metal ion detection. The dual click reactions were smoothly proceeded under microwave irradiation between silylated 3,4-di-O-propynyl gluco- or galactoside and 3-azidocoumarin, forming fluorescently reactivated bis-triazolocoumarins on sugar templates. Subsequent desilylation resulted in the OH-glycosides with desired water solubility. The following photochemical study disclosed that their fluorescence could be uniquely quenched by silver(I) in aqueous media with very minor responses to the addition of other metal ions. This research would presumably prompt the efficient creation of water soluble and potentially low toxic chemosensors via the fluorogenic dual click chemistry in using the universally existent sugars as the central scaffold.
- Published
- 2011
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24. A unique and rapid approach toward the efficient development of novel protein tyrosine phosphatase (PTP) inhibitors based on ‘clicked’ pseudo-glycopeptides
- Author
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Xiao-Peng He, Jia Li, Juan Xie, Cui Li, Li Sheng, Xiao-Xin Shi, Guo-Rong Chen, Li-Xin Gao, Jin-Wei Yang, and Yun Tang
- Subjects
Azides ,Molecular model ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Protein tyrosine phosphatase ,Biochemistry ,Catalysis ,Galactosides ,Drug Discovery ,Humans ,cdc25 Phosphatases ,Computer Simulation ,Enzyme Inhibitors ,Microwaves ,Molecular Biology ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,chemistry.chemical_classification ,Binding Sites ,biology ,Organic Chemistry ,Glycopeptides ,Stereoisomerism ,Amino acid ,Enzyme ,chemistry ,Docking (molecular) ,Enzyme inhibitor ,Alkynes ,Click chemistry ,biology.protein ,Molecular Medicine ,Click Chemistry ,Protein Tyrosine Phosphatases ,Copper - Abstract
There has been considerable interest in the development of protein tyrosine phosphatase (PTP) inhibitors since many of the PTP members are tightly associated with major human diseases including autoimmune disorders, diabetes and cancer. We report here a unique and rapid approach toward the development of novel PTP inhibitor entities based on triazolyl pseudo-glycopeptides. By employing microwave-accelerated Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC or ‘click reaction’), a series of triazole-linked serinyl, threoninyl, phenylalaninyl and tyrosinyl 1-O-gluco- or galactosides have been efficiently synthesized in high yields within only ∼30 min. Successive biological assay identified these glycopeptidotriazoles as favorable PTP1B and CDC25B inhibitors with selectivity over TCPTP, LAR, SHP-1 and SHP-2. Both the structural diversity of the amino acid (Ser, Thr, Phe and Tyr) introduced and the epimeric identity (Glc or Gal) on monosaccharide scaffold were determined to impact the corresponding inhibitory activity and selectivity. In addition, the benzylated sugar scaffold was demonstrated to act as a crucial role for enhancing the binding affinity of the inhibitors with the targeted PTP. Docking simulation was eventually conducted to propose plausible binding modes of this compound series with PTP1B and CDC25B. Our approach readily realized from naturally abundant raw materials (sugar and amino acid) and via facile, regioselective and expeditious synthetic method (microwave-assisted click reaction) might provide new insights toward the ‘click’ fabrication of structurally diverse PTP inhibitors.
- Published
- 2011
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25. ‘Click’ to bidentate bis-triazolyl sugar derivatives with promising biological and optical features
- Author
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Jia Li, Li-Xin Gao, Li Sheng, Zhuo Song, Guo-Rong Chen, Xiao-Peng He, Xiao-Ping Jin, and Yubo Zhou
- Subjects
Sugar derivatives ,Denticity ,Chemistry ,Stereochemistry ,Organic Chemistry ,Drug Discovery ,Click chemistry ,Sugar ,Biochemistry ,Protein Tyrosine Phosphatase 1B ,Cycloaddition - Abstract
Bidentate 1-O-methyl-α- d -pyranoglucosides bearing two triazolyl α-ketoester groups on the 2,6- or 3,4-positions of sugar scaffold were efficiently synthesized via Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (click reaction) in good yields. These newly featured sugar derivatives displayed favorable inhibitory activity on protein tyrosine phosphatase 1B (PTP1B) and unexpected selective fluorescence quenching in the presence of Ni2+.
- Published
- 2011
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- View/download PDF
26. Expeditious preparation of triazole-linked glycolipids via microwave accelerated click chemistry and their electrochemical and biological assessments
- Author
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Chol-Guk Kim, Guo-Rong Chen, Yi-Tao Long, Jia Li, Shao-Xing Song, Hai-Lin Zhang, Li Sheng, and Xiao-Peng He
- Subjects
Cyclic compound ,Chemistry ,Organic Chemistry ,Triazole ,Biochemistry ,Chemical synthesis ,Cycloaddition ,chemistry.chemical_compound ,Hydrogenolysis ,Drug Discovery ,1,3-Dipolar cycloaddition ,Click chemistry ,Organic chemistry ,Azide - Abstract
A series of triazole-linked ester-type glycolipids were efficiently prepared via a two-step sequence involving microwave accelerated ‘click’ chemistry and debenzylation. All carbon chain length varied O-alkynyl fatty esters used to couple with 1-azido-tetra-O-benzyl-β- d -glucoside showed excellent tolerance to the microwave-assisted 1,3-dipolar cycloaddition (click reaction), forming the unique cycloadducts in almost quantitative yields of 92.9–99.0% within a quarter. The desired glycolipids were then readily afforded via the successive hydrogenolysis promoted by PdCl2/H2. Their adsorption competence on gold electrode were evaluated through EIS (electrochemical impedance spectroscopy) measurement and the resulting structure–activity relationship (SAR) was discussed. In addition, the cytotoxicity of this triazolyl glycolipid class on HeLa (cervix cancer) cell line was identified by MTT assay.
- Published
- 2010
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27. One-step selective synthesis of branched 1-O-alkyl-glycerol/diglycerol monoethers by catalytic reductive alkylation of ketones
- Author
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Guo-Rong Chen, Yan Shi, Wissam Dayoub, and Marc Lemaire
- Subjects
chemistry.chemical_classification ,chemistry.chemical_compound ,Chemistry ,Hydrogen pressure ,High selectivity ,Glycerol ,Organic chemistry ,One-Step ,General Chemistry ,Alkylation ,Brønsted–Lowry acid–base theory ,Alkyl ,Catalysis - Abstract
Branched 1-O-alkyl glycerol and diglycerol monoethers were obtained in good yields and high selectivity by a straightforward catalytic reductive alkylation of glycerol with relevant ketones in the presence of 0.5 mol% of Pd/C under 10 bar of hydrogen pressure using a Bronsted acid as the co-catalyst.
- Published
- 2010
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28. Concise synthesis of five-membered ring carbasugars based on key ring-closing metathesis
- Author
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Huijin Feng, Yuanchao Li, Zheng Li, Yaxi Yang, and Guo-Rong Chen
- Subjects
Ring-closing metathesis ,Olefin metathesis ,Bicyclic molecule ,Stereochemistry ,Chemistry ,Organic Chemistry ,Drug Discovery ,Enantioselective synthesis ,Carbasugars ,Trehazolin ,Ring (chemistry) ,Metathesis ,Biochemistry - Abstract
A simple and efficient approach to the synthesis of five-membered ring carbasugars is achieved starting from readily available (R)-2,3-O-isopropylideneglyceraldehyde (2) through key ring-closing metathesis (RCM) in high overall yield. We have also confirmed its viability by preparing the core bicyclo [3.1.0] hexane framework presented in the potent antiviral nucleoside N-MCT 1.
- Published
- 2010
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29. Phase-Transfer Catalysed Enantioselective Epoxidation of Estra-Δ5(10),9(11)-diene Using Chiral Ammonium Salts Derived from Cinchona Alkaloids
- Author
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Yaxi Yang, Guo-Rong Chen, Zheng Li, and Yuanchao Li
- Subjects
chemistry.chemical_compound ,chemistry ,Diene ,Phase (matter) ,Organic Chemistry ,Enantioselective synthesis ,Epoxide ,Organic chemistry ,Ammonium ,Cinchona Alkaloids ,Biochemistry ,Catalysis - Abstract
A modified phase-transfer catalysed enantioselective epoxidation of estra-Delta(5(10),9(11))-diene, an important intermediate of anti-early pregnancy drug mifepristone 1, have been determined and investigated. Eight chiral ammonium salts (PTC A-H), used as phase-transfer catalysts, have been synthesized from cinchona alkaloids. Among them, PTC G and PTC H have exhibited satisfying catalytic activity to improve the ratio of alpha/beta epoxide up to 7:1.
- Published
- 2010
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30. Isolation and Structural Elucidation of Related Impurities in Canrenone
- Author
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Guo-Rong Chen and Ya-Xi Yang
- Subjects
Chromatography ,Chemistry ,medicine ,Organic chemistry ,General Chemistry ,Mother liquor ,Canrenone ,Isolation (microbiology) ,Related impurities ,medicine.drug - Abstract
Ten steroidal compounds as impurities in canrenone were isolated from the enriched mother liquor by using various chromatographic methods. Their structures were elucidated by spectrometric analysis, among which three new compounds were characterized as 3-(3-oxo-7α-(ethoxycarbonyl)methyl-17β-hydroxy-4-androsten-17α-yl) propionic acid γ-lactone (1), 3-(3-oxo-7α-ethoxy-17β-hydroxy-4-androsten-17α-yl) propionic acid γ-lactone (2) and 3-(3-oxo5β-propionic acid-γ-lactone-6β,17β-hydroxy-4-androstan-17α-yl) propionic acid γ-lactone (3).
- Published
- 2009
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31. β-C-Glycosiduronic acids and β-C-glycosyl compounds: New PTP1B inhibitors
- Author
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Guo-Rong Chen, Qiang Shen, Juan Xie, and Li Lin
- Subjects
Stereochemistry ,Chemistry, Pharmaceutical ,Clinical Biochemistry ,Carbohydrates ,Pharmaceutical Science ,Uronic acid ,Biochemistry ,Chemical synthesis ,Inhibitory Concentration 50 ,Structure-Activity Relationship ,chemistry.chemical_compound ,Drug Discovery ,Diabetes Mellitus ,Humans ,Glycosyl ,Glycosides ,Enzyme Inhibitors ,Beta (finance) ,Molecular Biology ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,chemistry.chemical_classification ,biology ,Aryl ,Organic Chemistry ,Quinones ,Quinone ,Uronic Acids ,Enzyme ,Models, Chemical ,chemistry ,Enzyme inhibitor ,Drug Design ,biology.protein ,Molecular Medicine ,hormones, hormone substitutes, and hormone antagonists - Abstract
Beta-C-glycosiduronic acid quinones and beta-C-glycosyl compounds have been synthesized as sugar-based PTP1B inhibitors. Benzoyl protected quinone derivatives (14 and 35) as well as aryl beta-C-glycosyl compounds (18, 22, 23 and 34) showed IC(50) values of 0.77-5.27 microM against PTP1B, with compounds 18 and 23 bearing an acidic function being the most potent.
- Published
- 2008
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32. Synthesis of triazole-linked β-C-glycosyl dimers as inhibitors of PTP1B
- Author
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Guo-Rong Chen, Li Lin, Juan Xie, and Qiang Shen
- Subjects
Stereochemistry ,Dimer ,Clinical Biochemistry ,Triazole ,Pharmaceutical Science ,1,4-Naphthoquinone ,Biochemistry ,Chemical synthesis ,Inhibitory Concentration 50 ,chemistry.chemical_compound ,Drug Discovery ,Benzoquinones ,Hypoglycemic Agents ,Glycosyl ,Glycosides ,Enzyme Inhibitors ,Molecular Biology ,Protein Tyrosine Phosphatase, Non-Receptor Type 1 ,Organic Chemistry ,Quinone ,carbohydrates (lipids) ,Diabetes Mellitus, Type 2 ,chemistry ,1,3-Dipolar cycloaddition ,Click chemistry ,Molecular Medicine ,Dimerization - Abstract
Protein tyrosine phosphatase 1B (PTP1B) has emerged as a promising target for type 2 diabetes. We have successfully synthesized dimeric acetylated and benzoylated β-C- d -glucosyl and β-C- d -galactosyl 1,4-dimethoxy benzenes or naphthalenes by click chemistry. These compounds were further transformed into the corresponding β-C- d -glycosyl-1,4-quinone derivatives by CAN oxidation. The in vitro inhibition test showed that dimeric benzoylated β-C- d -glycosyl 1,4-dimethoxybenzenes or 1,4-benzoquinones were good inhibitors of PTP1B (IC50: 0.62–0.88 μM), with no significant difference between gluco and galacto derivatives.
- Published
- 2008
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33. Synthesis of novel photolabile glycosides from methyl 4,6-O-(o-nitro)benzylidene-α-d-glycopyranosides
- Author
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Hua Yi, Guo-Rong Chen, Chen-Jiang Zhu, and Juan Xie
- Subjects
chemistry.chemical_classification ,Stereochemistry ,Chemistry ,Organic Chemistry ,Glycoside ,Regioselectivity ,Cleavage (embryo) ,Biochemistry ,chemistry.chemical_compound ,Reagent ,Yield (chemistry) ,Drug Discovery ,Nitro ,Benzyl group ,Epimer - Abstract
Novel photolabile sugar derivatives bearing a 4- or 6- O -( o -nitro)benzyl group have been prepared from the corresponding methyl 4,6- O -( o -nitro)benzylidene α- d -glycopyranosides. Regioselective cleavage with BF 3 ·Et 2 O/Et 3 SiH led to the methyl 6- O -( o -nitro)benzyl gluco - and manno -α- d -glycopyranosides 3 and 6 . Inversion of configuration at 4-OH position of gluco and manno derivatives offered the otherwise inaccessible methyl 6- O -( o -nitro)benzyl galacto - and talo -α- d -glycopyranosides 4 , 5 , and 7 . Careful reaction with PhBCl 2 /Et 3 SiH (3 equiv of reagents, 10 min at −78 °C) led to the desired methyl 4- O -( o -nitro)benzyl gluco - and manno -α- d -glycopyranosides 8 and 9 in very good yield. However, prolonged reaction with 6 equiv of PhBCl 2 /Et 3 SiH transformed the methyl 4,6- O -( o -nitro)benzylidene α- d -glucopyranoside 11 into the reduced d -glucitol derivative 15 . Oxidative cleavage of 5,6-diol function of 15 gave the corresponding photolabile l -xylose 17 . The photolabile glucosides 3 and 8 have been further transformed into the photolabile α- C -allyl d -glucopyranosides 20 and 22 .
- Published
- 2008
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34. C-D-Glucopyranosyl Derivatives of Tocopherols – Synthesis and Evaluation as Amphiphilic Antioxidants
- Author
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Olivier Dangles, Jean-Pierre Praly, Guo-Rong Chen, Li He, Bernard Fenet, Stéphanie Galland, and Claire Dufour
- Subjects
Antioxidant ,medicine.medical_treatment ,Organic Chemistry ,Alcohol ,Micelle ,carbohydrates (lipids) ,chemistry.chemical_compound ,Phytol ,Electrophilic substitution ,chemistry ,medicine ,Moiety ,Organic chemistry ,Tocopherol ,Physical and Theoretical Chemistry ,Ceric ammonium nitrate - Abstract
Treatment of dimethylhydroquinone dimethyl ethers (ortho and meta isomers) with glycopyranose pentaacetates (D-gluco, D-galacto) in the presence of SnCl4 and F3CCO2Ag selectively afforded the corresponding C-β-D-glycosyl derivatives by aromatic electrophilic substitution. Oxidation of the dimethoxybenzene moiety with ceric ammonium nitrate delivered C-β-D-glycosyl-dimethylbenzoquinones, which were reduced with Na2S2O4 to the corresponding C-β-D-glycosyl-dimethylhydroquinones. ZnCl2-catalyzed cyclization either with methylbut-2-en-1-ol (prenyl alcohol) or with all-racemic phytol led to acetyl-protected C-β-D-glycosyl chromanols or C-β-D-glycosyl tocopherols, the sugar residues of which were deacetylated under base catalysis conditions. These new molecules were evaluated as antioxidants in terms of their ability to inhibit the peroxidation of linoleic acid in SDS micelles. The position of the C-glucosyl moiety on the phenolic nucleus emerges as the critical structural determinant of their activity. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)
- Published
- 2008
- Full Text
- View/download PDF
35. Synthesis of β-C-glycopyranosyl-1,4-naphthoquinone derivatives and their cytotoxic activity
- Author
-
Li Lin, Guo-Rong Chen, Qing Xu, Juan Xie, and Xiao-Peng He
- Subjects
Cell Survival ,Stereochemistry ,macromolecular substances ,1,4-Naphthoquinone ,A375 cell ,Biochemistry ,Analytical Chemistry ,Structure-Activity Relationship ,Electrophilic substitution ,chemistry.chemical_compound ,Cell Line, Tumor ,Humans ,Cytotoxic T cell ,Glycosyl ,Glycosides ,Cytotoxicity ,chemistry.chemical_classification ,Molecular Structure ,Organic Chemistry ,Glycoside ,General Medicine ,In vitro ,carbohydrates (lipids) ,chemistry ,lipids (amino acids, peptides, and proteins) ,Naphthoquinones - Abstract
β- C -Glucosyl and β- C -galactosyl-1,4-dimethoxynaphthalenes have been synthesized using a F 3 CCO 2 Ag/SnCl 4 promoted Friedel–Crafts electrophilic substitution reaction. Both glycosyl acetates and methyl glycosides can be used as glycosyl donors. Further oxidation afforded the corresponding β- C -glycosyl-1,4-naphthoquinones. The in vitro cytotoxic activity of these compounds was evaluated against the A375 cell line.
- Published
- 2008
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- View/download PDF
36. Free-radical and ionic routes towards hydrolytically stable and bioactive C-glycosyl compounds
- Author
-
Jean-Pierre Praly and Guo-Rong Chen
- Subjects
Addition reaction ,General Chemical Engineering ,Radical ,Free-radical reaction ,General Chemistry ,Chemical synthesis ,Medicinal chemistry ,Quinone ,carbohydrates (lipids) ,chemistry.chemical_compound ,Electrophilic substitution ,chemistry ,Organic chemistry ,lipids (amino acids, peptides, and proteins) ,Glycosyl ,Acrylonitrile - Abstract
Photo-initiated addition of glycopyranosyl radicals to such radical acceptors as allyltributyltin, acrylonitrile, or diethyl vinylphosphonate was efficiently achieved to afford stereoselectively α-configured C -glycosyl compounds. With acrylonitrile or diethyl vinylphosphonate, catalytic amounts of organotin were used with NaBH 3 CN in excess. C-1 Sugar dihalides may be converted into the β-configured C -glycosyl analogues in two radical steps (C–C bond formation, reduction), or into bis- C , C -glycosides (two C–C bond forming reactions in one pot). These dihalides also opened the first access to C -glycodienes. C -Glycosyl-ethylphosphonic acids were elaborated into non-isosteric C -glycosyl mimics of natural sugar nucleotide diphosphates, which were evaluated as inhibitors of glycosyl transferases. In another approach, aromatic electrophilic substitution of 1,4-dimethoxybenzene by d -glycopyranosylium ions gave access to C -glycosyl derivatives of 1,4-dimethoxybenzene hydroquinone, and 1,4-benzoquinone. Some were found to inhibit protein tyrosine phosphatase 1B (PTP1B) and glycogen phosphorylase (GP), as shown by enzymatic and crystallographic studies. Extension of the synthetic work led to C -glycosyl-chromanols and C -glycosyl-tocopherols, which have been studied as anti-oxidants.
- Published
- 2008
- Full Text
- View/download PDF
37. C-Glycosyl Amino-Substituted Hydro- and Benzoquinones: Synthesis and Preliminary Biological Evaluation
- Author
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Jean-Pierre Praly, Kaïss Aouadi, Guo-Rong Chen, and Yun Zhi Zhang
- Subjects
chemistry.chemical_classification ,Organic Chemistry ,Glycoside ,Electrophilic aromatic substitution ,Catalysis ,Quinone ,chemistry.chemical_compound ,chemistry ,Nitrate ,Amide ,Nitro ,Organic chemistry ,Glycosyl - Abstract
Reaction of C-β-D-glycopyranosyl-1,4-dimethoxybenzenes with acetyl nitrate afforded 2-(β-D-glycopyranosyl)-1,4-dimethoxy-5-nitrobenzenes in high yields. These were converted smoothly (reduction to amines, N-acylation, oxidation, and reduction) into the corresponding C-glycosyl-hydro(benzo)quinone derivatives, with different amide-based substituents at C-5. Reduction of the nitro compounds to amines proceeded smoothly by catalytic hydrogen transfer with HCO 2 NH 4 .
- Published
- 2007
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38. In the Search of Glycogen Phosphorylase Inhibitors: Synthesis of C-D-Glycopyranosylbenzo(hydro)quinones – Inhibition of and Binding to Glycogen Phosphorylase in the Crystal
- Author
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Evangelia D. Chrysina, Magda Kosmopoulou, C. Tiraidis, Guo-Rong Chen, Li He, Nikos G. Oikonomakos, Jean-Pierre Praly, Marcelle Tanoh, Demetres D. Leonidas, and Yun Zhi Zhang
- Subjects
Electrophilic substitution ,Glycogen phosphorylase ,Chemistry ,Acetylation ,Stereochemistry ,Organic Chemistry ,Transferase ,Substrate (chemistry) ,Crystal structure ,Physical and Theoretical Chemistry ,Electrophilic aromatic substitution ,Catalysis - Abstract
Penta-O-acetyl-β-D-glycopyranoses and 1,4-dimethoxybenzene led selectively by electrophilic substitution to C-β-D-glycopyranosyl-1,4-dimethoxybenzenes which were converted by simple and efficient reactions (oxidation, reduction and deacetylation) to the corresponding C-glycosylhydro- and C-glycosylbenzoquinones, with either an acetylated or deprotected sugar moiety. C-β-D-Glucosylbenzoquinone 19 and C-β-D-Glucosylhydroquinone 23 were found to be competitive inhibitors of rabbit muscle glycogen phosphorylase b (GPb), with respect to the substrate α-D-glucose-1-phosphate, with Ki values of 1.3 and 0.9 mM, respectively, whereas C-β-D-glucosylhydroquinone 17 was not effective up to a concentration of 8 mM. In order to elucidate the structural basis of inhibition, we determined the crystal structures of 19 and 23 in complex with GPb at a 2.03–2.05 A resolution. The complex structures reveal that the inhibitors can be accommodated at the catalytic site at approximately the same position as α-D-glucose and stabilise the transition state conformation of the 280s loop by making several favourable contacts to Asp283 and Asn284 of this loop. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
- Published
- 2007
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39. Photoluminescence of ZnO-aggregates in oxide glasses
- Author
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Tsuguo Fukuda, Jian Zhang, R. Jinhua, Alena Beitlerova, Guo-Rong Chen, Martin Nikl, Akira Yoshikawa, and J. Pejchal
- Subjects
Photoluminescence ,Organic Chemistry ,Kinetics ,Analytical chemistry ,Oxide ,Mineralogy ,Condensed Matter::Disordered Systems and Neural Networks ,Atomic and Molecular Physics, and Optics ,Spectral line ,Electronic, Optical and Magnetic Materials ,Inorganic Chemistry ,Condensed Matter::Materials Science ,Emission band ,chemistry.chemical_compound ,chemistry ,Optical materials ,Electrical and Electronic Engineering ,Physical and Theoretical Chemistry ,Luminescence ,Chemical composition ,Spectroscopy - Abstract
Photoluminescence spectra and decay kinetics at room temperature were studied at the set of ZnO-containing mixed-oxide glasses of various compositions. The dominant broad emission band peaking round 390 nm is observed in most of the glasses regardless of their chemical composition. This emission is ascribed to the ZnO-aggregates originating both in their volume and at the interface with the glass host.
- Published
- 2007
- Full Text
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40. C-Glycopyranosyl-1,4-benzoquinones and -hydroquinones opening access to C-glycosylated analogs of vitamin E
- Author
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Li He, Guo-Rong Chen, Bing Bing Qin, Marcelle Tanoh, and Jean-Pierre Praly
- Subjects
animal structures ,Chemistry ,Stereochemistry ,Vitamin E ,medicine.medical_treatment ,Organic Chemistry ,macromolecular substances ,Biochemistry ,carbohydrates (lipids) ,Acetylation ,Drug Discovery ,medicine ,Organic chemistry ,lipids (amino acids, peptides, and proteins) ,Sugar moiety - Abstract
2-(Per-O-acetyl-β-d-glycopyranosyl)-1,4-dimethoxybenzenes led to C-glycosyl-hydroquinones suitable for preparing C-glycosylated analogs of vitamin E, having the sugar moiety free or acetylated.
- Published
- 2005
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41. The anomeric mixture of some O-galactolipid derivatives is more toxic against cancer cells than either anomer alone
- Author
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Yubo Zhou, Guo-Rong Chen, Li Sheng, Jia Li, Shao-Xing Song, Xiao-Peng He, and Ming-Li Wu
- Subjects
Galactolipid ,Glycosylation ,Anomer ,Cell Survival ,Stereochemistry ,Clinical Biochemistry ,Pharmaceutical Science ,Antineoplastic Agents ,Biochemistry ,chemistry.chemical_compound ,Glycolipid ,Cell Line, Tumor ,Neoplasms ,Drug Discovery ,Humans ,Cytotoxicity ,Molecular Biology ,Alkyl ,chemistry.chemical_classification ,Chemistry ,Galactolipids ,Single component ,Organic Chemistry ,Drug Synergism ,Cancer cell ,Molecular Medicine ,lipids (amino acids, peptides, and proteins) - Abstract
The anomeric mixture of a series of O-galactolipid derivatives is revealed to be more toxic against several cancer cell lines than their either single component with the pure α- or β-configuration. This interesting phenomenon has been confirmed on pairs of synthesized O-galactosyl anomers bearing length-varied alkyl chains at the lipid end. Furthermore, the most potent mixture was determined inoffensive to a normal cell line tested.
- Published
- 2012
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42. ChemInform Abstract: Transition Metal-Free Cascade Reactions of Alkynols to Afford Isoquinolin-1(2H)-one and Dihydroisobenzofuran Derivatives
- Author
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Deng Yuan Li, Guo Rong Chen, Ke Ji Shi, Xiao Feng Mao, and Pei Nian Liu
- Subjects
Solvent ,Cascade reaction ,Transition metal ,Chemistry ,Computational chemistry ,Cascade ,Organic chemistry ,General Medicine - Abstract
The result of the title cascade reaction of alkynols with imines depends on the solvent used (DMSO or THF).
- Published
- 2014
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43. Rhodium-catalyzed addition-cyclization of hydrazines with alkynes: pyrazole synthesis via unexpected C-N bond cleavage
- Author
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Deng Yuan Li, Pei Nian Liu, Xiao Feng Mao, Guo Rong Chen, and Hao Jie Chen
- Subjects
Stereochemistry ,Organic Chemistry ,chemistry.chemical_element ,Pyrazole ,Biochemistry ,Medicinal chemistry ,Chemical reaction ,Rhodium ,Catalysis ,chemistry.chemical_compound ,chemistry ,Chemical bond ,Cascade reaction ,Intramolecular force ,Physical and Theoretical Chemistry ,Bond cleavage - Abstract
Rhodium-catalyzed addition-cyclization of hydrazines with alkynes has been achieved to afford highly substituted pyrazoles under mild conditions. The cascade reaction involves two transformations: addition of the C-N bond of hydrazines to alkynes via unexpected C-N bond cleavage and intramolecular dehydration cyclization.
- Published
- 2014
44. Transition metal-free cascade reactions of alkynols to afford isoquinolin-1(2H)-one and dihydroisobenzofuran derivatives
- Author
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Xiao Feng Mao, Guo Rong Chen, Pei Nian Liu, Deng Yuan Li, and Ke Ji Shi
- Subjects
Aldehydes ,Natural product ,Molecular Structure ,Chemistry ,Potassium ,Organic Chemistry ,Berberine Alkaloids ,chemistry.chemical_element ,Isoquinolines ,Catalysis ,Solvent ,chemistry.chemical_compound ,Transition metal ,Cascade ,Yield (chemistry) ,Transition Elements ,Organic chemistry ,Amines ,Benzofurans - Abstract
Transition metal-free cascade reactions of alkynols with imines have been achieved using potassium tert-butoxide as catalyst. Switching the reaction solvent gives two kinds of products in good yield: isoquinolin-1(2H)-one derivatives and dihydroisobenzofuran derivatives. This approach was used to generate the natural product 8-oxypseudopalmatine in a two-step procedure from commercially available starting materials. Additionally, multicomponent reactions of alkynols, aldehydes, and amines were also successfully achieved to afford isoquinolin-1(2H)-one derivatives.
- Published
- 2014
45. Construction of 6-Triazole-Linked Mannopyranosyl Serine and Threonine as Novel Sugar Amino Acid Mimics
- Author
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Xiao-Peng He, Qiong Deng, Guo-Rong Chen, Na-Na Ding, and Rong-Rong Zheng
- Subjects
chemistry.chemical_classification ,Serine ,chemistry.chemical_compound ,chemistry ,Triazole ,Click chemistry ,Organic chemistry ,General Chemistry ,Sugar amino acid ,Threonine ,Photo-reactive amino acid analog ,Amino acid synthesis ,Amino acid - Published
- 2010
- Full Text
- View/download PDF
46. Stereocontrolled Access to Higher Sugars (Non-1-en-4-ulopyranosyl Derivatives) and Glycomimetics [3-(β-D-Glycopyranosyl)-1-propenes and(3Z)-4,8-Anhydro-nona-1,3-dienitols]
- Author
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Guo-Rong Chen, Joëlle Gola, Georg Hetzer, and Jean-Pierre Praly
- Subjects
chemistry.chemical_classification ,Hydrolysis ,Quenching (fluorescence) ,Chemistry ,Radical ,Yield (chemistry) ,Organic Chemistry ,Enantioselective synthesis ,Glycoside ,Organic chemistry ,Epimer ,Stereoselectivity ,Physical and Theoretical Chemistry - Abstract
Peracetylated 1-bromo-β-D-glycopyranosyl chlorides react with allyltributyltin under photolytic conditions to afford the corresponding acetylated α-D-non-1-en-4-ulopyranosyl chlorides. Yields vary, depending mainly on the parent sugar configuration (D-gluco: 86%; D-galacto: 51%; D-manno: 31%). The corresponding acetylated α-D-non-1-en-4-ulopyranoses resulting from hydrolysis were obtained as by-products (8−23% yield). Radical reduction of the acetylated α-D-non-1-en-4-ulopyranosyl chlorides, mediated by nBu3SnH, led to glycopyranos-1-yl radicals, the diastereoselective quenching of which produced acetylated 3-(β-D-glycopyranosyl)-1-propenes in good overall yield (50−57% yield). This approach, which combines C−C and C−H bond forming reactions involving glycopyranosyl radicals, constitutes a more efficient route to acetylated 3-(β-D-glycopyranosyl)-1-propenes. No traces of the 3-(α-D-glycopyranosyl)-1-propene epimers could be detected, so the diastereoselectivity of the radical-mediated reduction controlling the product structure was ascertained to be >95:5. On treatment with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), the acetylated 4-ulopyranosyl chlorides underwent stereoselective dehydrochlorination to afford new (3Z)-4,8-anhydronona-1,3-dienitols (42−63% yield), which could be deacetylated. Since these syntheses can be carried out by one-pot procedures, this work opens up easy access to unsaturated C-glycopyranosyl compounds which are otherwise difficult to prepare or are completely unknown.
- Published
- 2000
- Full Text
- View/download PDF
47. Straightforward selective synthesis of linear 1-O-alkyl glycerol and di-glycerol monoethers
- Author
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Wissam Dayoub, Guo-Rong Chen, Marc Lemaire, Alain Favre-Réguillon, Yan Shi, Institute of Materials Science and Engineering, East China University of Science and Technology, East China University of Science and Technology, Institut de Chimie et Biochimie Moléculaires et Supramoléculaires (ICBMS), Université Claude Bernard Lyon 1 (UCBL), Université de Lyon-Université de Lyon-Institut National des Sciences Appliquées de Lyon (INSA Lyon), and Université de Lyon-Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-École Supérieure Chimie Physique Électronique de Lyon-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)
- Subjects
1-O-Alkyl mono ,Glycerol ,chemistry.chemical_classification ,Hydrogen ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Organic Chemistry ,chemistry.chemical_element ,Di-glycerol ,Reductive alkylation ,010402 general chemistry ,01 natural sciences ,Biochemistry ,0104 chemical sciences ,Catalysis ,chemistry.chemical_compound ,chemistry ,di-glycerol monoethers ,Drug Discovery ,Organic chemistry ,Selectivity ,Brønsted–Lowry acid–base theory ,Alkyl - Abstract
International audience; 1-O-Alkyl glycerol and di-glycerol monoethers are, respectively, obtained in high yields and selectivity by catalytic reductive etherification of mono- and di-glycerol with linear aldehydes in the presence of 0.5 mol % of Pd/C under 10 bars of hydrogen using a Brønsted acid as co-catalyst.
- Published
- 2009
- Full Text
- View/download PDF
48. A new synthesis of α-arbutin via Lewis acid catalyzed selective glycosylation of tetra-O-benzyl-α-d-glucopyranosyl trichloroacetimidate with hydroquinone
- Author
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Guo-Rong Chen, Xiao-Xin Shi, Lei Luo, Zhi-Hua Ren, Jing Yan, and Zhao-Xia Wang
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Glycosylation ,Anomer ,Stereochemistry ,Biochemistry ,Chemical synthesis ,Catalysis ,Analytical Chemistry ,chemistry.chemical_compound ,Trimethylsilyl trifluoromethanesulfonate ,Acetamides ,polycyclic compounds ,Chloroacetates ,heterocyclic compounds ,Lewis acids and bases ,Trichloroacetic Acid ,Glycosyl donor ,Molecular Structure ,Hydroquinone ,organic chemicals ,Organic Chemistry ,Arbutin ,General Medicine ,Hydroquinones ,carbohydrates (lipids) ,Models, Chemical ,chemistry ,Acids - Abstract
alpha-Arbutin has huge application potentials in the cosmetic industry, as its inhibitory effect on human tyrosinase is stronger than that of its naturally occurring anomer arbutin (4-hydroxyphenyl beta-D-glucopyranoside). Enzymatic synthesis was preferred for alpha-arbutin previously, and now a new chemical synthesis is reported. The reaction of tetra-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate, as glycosyl donor, with hydroquinone was initiated by catalytic amounts of trimethylsilyl trifluoromethanesulfonate (TMSOTf), resulting in 4-hydroxyphenyl 2,3,4,6-tetra-O-benzyl-alpha-D-glucopyranoside with high stereoselectivity and yield, and then to alpha-arbutin quantitatively after deprotection.
- Published
- 2006
- Full Text
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49. A stereocontrolled radical access to C-allyl β-D-glycopyranosides from glycopyranosylidene dihalides found en route to C-glycodienes
- Author
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Christophe Raphoz, Guo-Rong Chen, Jean-Pierre Praly, Georg Hetzer, and Joëlle Gola
- Subjects
chemistry.chemical_classification ,chemistry ,Hydride ,Organic Chemistry ,Drug Discovery ,Glycoside ,Organic chemistry ,Biochemistry - Abstract
Application of the Keck reaction to peracetylated glycopyranosylidene dihalides under mild conditions led efficiently to chloro C-allyl glycosides which were converted to either the corresponding C-allyl β-D-glycosides of C-D-glycodienes on treatment with, respectively, tri-n-butyltin hydride and DBU.
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- 1997
- Full Text
- View/download PDF
50. Identification of a new bis-amino acid glycoside selectively toxic to multiple myeloma cells
- Author
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Jia Li, Xiao-Peng He, Yi Zang, Guo-Rong Chen, Chao-Ying Cheng, and Yan-Yan Feng
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Phenylalanine ,Antineoplastic Agents ,Apoptosis ,Cleavage (embryo) ,Biochemistry ,Analytical Chemistry ,chemistry.chemical_compound ,Western blot ,Cell Line, Tumor ,medicine ,Humans ,Glycosides ,Cytotoxicity ,Polymerase ,chemistry.chemical_classification ,medicine.diagnostic_test ,biology ,Chemistry ,Organic Chemistry ,General Medicine ,Galactoside ,Amino acid ,biology.protein ,Click Chemistry ,Drug Screening Assays, Antitumor ,Poly(ADP-ribose) Polymerases ,Multiple Myeloma - Abstract
A bis-triazolyl phenylalaninyl galactoside was synthesized by a two-fold click reaction between an azido phenylalanine and a di-O-propynyl galactoside. By a cytotoxicity assay the compound was determined to be selectively toxic for multiple myeloma (MM) among a series of cancer cell lines with no toxicity to a control cell line. A Western blot analysis suggested that this compound could potentiate the cleavage of poly ADP-ribose polymerase in MM cells, leading to apoptosis.
- Published
- 2013
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