Synthesis, α-glycosidase inhibitory potential and molecular docking study of benzimidazole derivatives

Muhammad Taha, Fazal Rahim, Khalid Zaman, Manikandan Selvaraj, Nizam Uddin, Rai Khalid Farooq, Muhammad Nawaz, Muhammad Sajid, Faisal Nawaz, Mohamad Ibrahim, Khalid Mohammed Khan

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18 Citations (Scopus)

Abstract

A series of twenty-six analogs of benzimidazole based oxadiazole have been synthesized and evaluated against alpha-glycosidase enzyme. Most the analogs showed excellent to good inhibitory potential. Among the screened analogs, analog 1, 2, 3 and 14 with IC50 values 4.6 ± 0.1, 9.50 ± 0.3, 2.6 ± 0.1 and 9.30 ± 0.4 µM respectively showedexcellent inhibitory potential than reference drug acarbose (IC50 = 38.45 ± 0.80 µM). Some of the analogs like 19, 21, 22 and 23 with methyl and methoxy substituent on phenyl ring show hydrophobic interaction and were found with no inhibitory potential. The binding interactions between synthesized analogs and ligands protein were confirmed through molecular docking study. Various spectroscopic techniques like 1H NMR, 13C NMR, and EI-MS were used for characterization of all synthesized analogs. These derivatives were synthesized by simple mode of synthesis like heterocyclic ring formation.

Original languageEnglish
Article number103555
Number of pages9
JournalBioorganic Chemistry
Volume95
DOIs
Publication statusPublished - Jan 2020

Keywords

  • Benzimidazole
  • Molecular docking
  • Oxadiazole
  • Synthesis
  • α-glycosidase inhibition

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