Synthesis of thiobarbituric acid derivatives: In vitro α-glucosidase inhibition and molecular docking studies

Synthesis, structure, and evaluation of in vitro alpha-glucosidase enzyme inhibition of a new class of diethylammonium salts of aryl substituted thiobarbituric acid is described. This protocol is straight, environmentally benign and efficient, involving Aldol-Michael addition reaction in one pot fashion. The 3D chemical structures of the synthesized compounds were assigned based on spectroscopic methods and X-ray single crystal diffraction analyses. All synthesized compounds 3a-3n were evaluated for their in vitro alpha-glucosidase enzyme inhibitory activity, whereas acarbose was used as the standard drug (IC50 = 840 +/- 1.73 mu M). All tested compounds were found to possess varying degree of a-glucosidase enzyme inhibition activity with (IC50 = 19.46 +/- 1.84-415.8 +/- 4.0 mu M). Compound 3i (IC50 = 19.4 +/- 1.84 mu M) exhibited the highest activity. To the best of knowledge this is the first report of the in vitro alpha-glucosidase enzyme inhibition by the diethylamonium salts of aryl substituted thiobarbituric acid. Furthermore, molecular docking studies of selected compounds were also performed to see interactions between active compounds and binding sites. (C) 2017 Elsevier Inc. All rights reserved.