Synthesis, α-glucosidase inhibitory, cytotoxicity and docking studies of 2-aryl-7-methylbenzimidazoles

Bioorg Chem. 2016 Apr:65:100-9. doi: 10.1016/j.bioorg.2016.02.004. Epub 2016 Feb 13.

Abstract

Benzimidazole analogs 1-27 were synthesized, characterized by EI-MS and (1)HNMR and their α-glucosidase inhibitory activities were found out experimentally. Compound 25, 19, 10 and 20 have best inhibitory activities with IC50 values 5.30±0.10, 16.10±0.10, 25.36±0.14 and 29.75±0.19 respectively against α-glucosidase. Compound 6 and 12 has no inhibitory activity against α-glucosidase enzyme among the series. Further studies showed that the compounds are not showing any cytotoxicity effect. The docking studies of the compounds as well as the experimental activities of the compounds correlated well. From the molecular docking studies, it was observed that the top ranked conformation of all the compounds fit well in the active site of the homology model of α-glucosidase.

Keywords: 4-Methylbenzimidazol; Antihyperglycemia; Cytotoxicity docking studies; Structure–activity relationship; α-glucosidase inhibitors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 3T3-L1 Cells
  • Animals
  • Benzimidazoles / chemical synthesis
  • Benzimidazoles / chemistry
  • Benzimidazoles / pharmacology*
  • Cell Line
  • Dose-Response Relationship, Drug
  • Glycoside Hydrolase Inhibitors / chemical synthesis
  • Glycoside Hydrolase Inhibitors / chemistry
  • Glycoside Hydrolase Inhibitors / pharmacology*
  • Glycoside Hydrolase Inhibitors / toxicity*
  • Mice
  • Molecular Docking Simulation*
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Structure-Activity Relationship
  • alpha-Glucosidases / metabolism*

Substances

  • Benzimidazoles
  • Glycoside Hydrolase Inhibitors
  • alpha-Glucosidases