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

Asgari, Mohammad Sadegh and Mohammadi‑Khanaposhtani, Maryam and Sharafi, Zeinab and Faramarzi, Mohammad Ali (2020) 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. Molecular Diversity.

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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

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