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

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 alpha-glucosidase, and all these compounds exhibited excellent inhibitory activity (IC50 values in the range of 85.6 +/- 0.4-231.4 +/- 1.0 muM), even much more potent than standard drug acarbose (IC50 = 750.0 muM). 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 alpha-glucosidase. The kinetic study of the compound 8g revealed that this compound inhibited alpha-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 alpha-glucosidase. A novel series of 4,5-diphenyl-imidazol-1,2,3-triazole hybrids 8a-n was synthesized with good yields by performing click reaction between the 4,5-diphenyl-2-(prop-2-yn-1-ylthio)-1Himidazole and various benzyl azides. The synthesized compounds 8a-n were evaluated against yeast alpha-glucosidase and all these compounds exhibited excellent inhibitory activity (IC50 values in the range of 85.6 +/- 0.4-231.4 +/- 1.0 muM), even much more potent than standard drug acarbose (IC50 = 750.0 muM).