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Design and Synthesis of 4,5-Diphenyl-Imidazol-1,2,3-Triazole Hybrids As New Anti-Diabetic Agents: In Vitro Α-Glucosidase Inhibition, Kinetic and Docking Studies Publisher Pubmed



Asgari MS1 ; Mohammadikhanaposhtani M2 ; Sharafi Z3 ; Faramarzi MA4 ; Rastegar H5 ; Nasli Esfahani E6 ; Bandarian F6 ; Ranjbar Rashidi P1 ; Rahimi R7 ; Biglar M8 ; Mahdavi M8 ; Larijani B8
Authors

Source: Molecular Diversity Published:2021


Abstract

Abstract: Fourteen novel 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n were synthesized with good yields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1H-imidazole and various benzyl azides. The synthesized compounds 8a–n were evaluated against yeast α-glucosidase, and all these compounds exhibited excellent inhibitory activity (IC50 values in the range of 85.6 ± 0.4–231.4 ± 1.0 μM), even much more potent than standard drug acarbose (IC50 = 750.0 μM). Among them, 4,5-diphenyl-imidazol-1,2,3-triazoles possessing 2-chloro and 2-bromo-benzyl moieties (compounds 8g and 8i) demonstrated the most potent inhibitory activities toward α-glucosidase. The kinetic study of the compound 8g revealed that this compound inhibited α-glucosidase in a competitive mode. Furthermore, docking calculations of these compounds were performed to predict the interaction mode of the synthesized compounds in the active site of α-glucosidase. Graphic abstract: A novel series of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a–n was synthesized with goodyields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1Himidazoleand various benzyl azides. The synthesized compounds 8a–n were evaluated againstyeast α-glucosidase and all these compounds exhibited excellent inhibitory activity (IC50 valuesin the range of 85.6 ± 0.4-231.4 ± 1.0 μM), even much more potent than standard drug acarbose(IC50 = 750.0 μM).[Figure not available: see fulltext.] © 2020, Springer Nature Switzerland AG.
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