Synthesis, in vitro and computational studies of novel glycosyl-1, 2, 3-1H-triazolyl methyl benzamide derivatives as potential α-glucosidase inhibitory activity

Abstract

A series of novel glycosyl-1,2,3-1H-triazolyl methyl benzamide analogues were synthesized by the unambiguous strategy and evaluated for α-glucosidase inhibitory activity. Glycosyl benzamide exhibited a dose-dependent inhibition of α-glucosidase activity. The In-vitro α-glucosidase inhibition activity results indicated that all the synthesized triazolyl methyl benzamide compounds (IC50 values ranging from 25.3 ± 0.8 to 118.5 ± 5.3 μM) exhibited more inhibitory activity in comparison with the standard drug acarbose (IC50 = 750.0 ± 12.5 μM). Among all, the 3 deacetylated glycosyl methyl benzamide derivatives (4c, 4d and 4f) showed promising α-glucosidase enzyme inhibitory activities with IC50 value 25.3 ± 0.8, 26.1 ± 1.5 and 30.6 ± 2.1 respectively. Furthermore, these compounds were subjected to molecular docking and molecular dynamics simulation studies. The molecular docking studies were performed between (PDB ID: 3A4A) target protein and these synthesized molecules. The compounds displayed good docking energies in the range of −7.5 to −7.8 Kcal/mol. This work could be used as an initial approach in identifying potential novel molecules with the promising activity of type-2 diabetes mellitus.