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Design, synthesis, biological evaluation, and docking study of new triazole-phenylacetamide derivatives as α-glucosidase inhibitors. 2023

Shuang Luo, and Wei Yang, and Yong Huang, and Zhiyun Peng, and Guangcheng Wang
State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Provincial Key Laboratory of Pharmaceutics, Guizhou Medical University, Guiyang, China; School of Pharmacy, Guizhou Medical University, Guiyang, China.

To discover potent α-glucosidase inhibitors, a class of novel triazole-phenylacetamide derivatives (5a-5p) were designed, prepared, and tested for their α-glucosidase inhibitory effects. All tested compounds (5a-5p) displayed a strong α-glucosidase inhibitory activity (IC50 = 6.69 ± 0.18-113.65 ± 2.94 μM) in comparison with the positive control acarbose (IC50 = 723.06 ± 11.26 μM). Thereinto, 5g (IC50 = 6.69 ± 0.18 μM) showed the best anti-α-glucosidase activity and behaved as a mixed-type inhibitor with the value of Ki and Kis to be 1.65 μM and 4.54 μM, respectively. Besides, fluorescence quenching experiment, three-dimensional fluorescence spectra assay, circular dichroism analysis, and molecular docking studies indicated that 5g may inhibit α-glucosidase activity by binding with its active site as well as changing the secondary structure of α-glucosidase. Combined with the inhibition effect on the rise of postprandial blood glucose level and low cytotoxicity of 5g, it could be concluded that these title compounds may play a role as lead compounds to develop novel α-glucosidase inhibitors.

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D000520 alpha-Glucosidases Enzymes that catalyze the exohydrolysis of 1,4-alpha-glucosidic linkages with release of alpha-glucose. Deficiency of alpha-1,4-glucosidase may cause GLYCOGEN STORAGE DISEASE TYPE II. Acid Maltase,Lysosomal alpha-Glucosidase,Maltase,Maltases,Maltase-Glucoamylase,Neutral Maltase,Neutral alpha-Glucosidase,alpha-Glucosidase,Lysosomal alpha Glucosidase,Maltase Glucoamylase,Neutral alpha Glucosidase,alpha Glucosidase,alpha Glucosidases,alpha-Glucosidase, Lysosomal,alpha-Glucosidase, Neutral
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular
D062105 Molecular Docking Simulation A computer simulation technique that is used to model the interaction between two molecules. Typically the docking simulation measures the interactions of a small molecule or ligand with a part of a larger molecule such as a protein. Molecular Docking,Molecular Docking Simulations,Molecular Docking Analysis,Analysis, Molecular Docking,Docking Analysis, Molecular,Docking Simulation, Molecular,Docking, Molecular,Molecular Docking Analyses,Molecular Dockings,Simulation, Molecular Docking
D065089 Glycoside Hydrolase Inhibitors Compounds that inhibit or block the activity of GLYCOSIDE HYDROLASES such as ALPHA-AMYLASES and ALPHA-GLUCOSIDASES. alpha-Glucosidase Inhibitor,alpha-Glucosidase Inhibitors,Intestinal alpha-Amylase Inhibitors,Pancreatic alpha-Amylase Inhibitors,alpha-Amylase Inhibitors, Pancreatic,Hydrolase Inhibitors, Glycoside,Inhibitor, alpha-Glucosidase,Inhibitors, Glycoside Hydrolase,Inhibitors, Intestinal alpha-Amylase,Inhibitors, Pancreatic alpha-Amylase,Inhibitors, alpha-Glucosidase,Intestinal alpha Amylase Inhibitors,Pancreatic alpha Amylase Inhibitors,alpha Amylase Inhibitors, Pancreatic,alpha Glucosidase Inhibitor,alpha Glucosidase Inhibitors,alpha-Amylase Inhibitors, Intestinal

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