Synthesis, in vitro evaluation and molecular docking studies of thiazole derivatives as new inhibitors of α-glucosidase

Bioorg Chem. 2015 Oct;62:15-21. doi: 10.1016/j.bioorg.2015.06.006. Epub 2015 Jun 29.

Abstract

A series of thiazole derivatives 1-21 were prepared, characterized by EI-MS and (1)H NMR and evaluated for α-glucosidase inhibitory potential. All twenty one derivatives showed good α-glucosidase inhibitory activity with IC50 value ranging between 18.23±0.03 and 424.41±0.94μM when compared with the standard acarbose (IC50, 38.25±0.12μM). Compound (8) (IC50, 18.23±0.03μM) and compound (7) (IC50=36.75±0.05μM) exhibited outstanding inhibitory potential much better than the standard acarbose (IC50, 38.25±0.12μM). All other analogs also showed good to moderate enzyme inhibition. Molecular docking studies were carried out in order to find the binding affinity of thiazole derivatives with enzyme. Studies showed these thiazole analogs as a new class of α-glucosidase inhibitors.

Keywords: Molecular docking; Synthesis; Thiazole; α-Glucosidase inhibition.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acarbose / pharmacology
  • Glycoside Hydrolase Inhibitors / chemical synthesis*
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Hydrazines / chemical synthesis*
  • Hydrazines / pharmacology*
  • Molecular Docking Simulation*
  • Phenols / chemical synthesis*
  • Phenols / pharmacology*
  • Saccharomyces cerevisiae Proteins / chemistry
  • Thiazoles / chemical synthesis*
  • Thiazoles / pharmacology*
  • alpha-Glucosidases / chemistry
  • alpha-Glucosidases / drug effects*

Substances

  • 2,6-di-t-butyl-4-((2-(4-(4-chlorophenyl)thiazole-2-yl)hydrazono)methyl)-phenol
  • 2-(2-(4-(benzyloxy)benzylidene)hydrazinyl)-4-(4-chlorophenyl)thiazole
  • Glycoside Hydrolase Inhibitors
  • Hydrazines
  • Phenols
  • Saccharomyces cerevisiae Proteins
  • Thiazoles
  • alpha-Glucosidases
  • Acarbose