Synthesis, in vitro α-glucosidase inhibitory potential and molecular docking study of thiadiazole analogs

alpha-Glucosidase is a catabolic enzyme that regulates the body's plasma glucose levels by providing energy sources to maintain healthy functioning. 2-Amino-thiadiazole (1-13) and 2-amino-thiadiazole based Schiff bases (14-22) were synthesized, characterized by H-1 NMR and HREI-MS and screened for aglucosidase inhibitory activity. All twenty-two (22) analogs exhibit varied degree of a-glucosidase inhibitory potential with IC50 values ranging between 2.30 +/- 0.1 to 38.30 +/- 0.7 mu M, when compare with standard drug acarbose having IC50 value of 39.60 +/- 0.70 mu M. Among the series eight derivatives 1, 2, 6, 7, 14, 17, 19 and 20 showed outstanding a-glucosidase inhibitory potential with IC50 values of 3.30 +/- 0.1, 5.80 +/- 0.2, 2.30 +/- 0.1, 2.70 +/- 0.1, 2.30 +/- 0.1, 5.50 +/- 0.1, 4.70 +/- 0.2, and 5.50 +/- 0.2 mu M respectively, which is many fold better than the standard drug acarbose. The remaining analogs showed good to excellent aglucosidase inhibition. Structure activity relationship has been established for all compounds. The binding interactions of these compounds were confirmed through molecular docking. (C) 2018 Elsevier Inc. All rights reserved.