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

Taha M 1 , Rahim F 2 , Zaman K 2 , Selvaraj M 3 , Uddin N 4 , Farooq RK 5 Show all authors , Nawaz M 6 , Sajid M 7 , Nawaz F 8 , Ibrahim M 9 , Khan KM 10

Affiliations 

  • 1 Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia. Electronic address: mtaha@iau.edu.sa
  • 2 Depatment of Chemistry, Hazara University, Mansehra 21300, Khyber Pakhtunkhwa, Pakistan
  • 3 Monash University School of Chemical Engineering, Bandar Sunway 47500 Selangor Darul Ehsan, Malaysia
  • 4 Department of Chemistry, University of Karachi, Karachi 75270, Pakistan
  • 5 Department of Neuroscience Research, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia
  • 6 Department of Nano-Medicine Research, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 1982, Dammam 31441, Saudi Arabia
  • 7 Department of Biochemistry, Hazara University, Mansehra 21300, Khyber Pakhtunkhwa, Pakistan
  • 8 Department of Chemistry, University of Wah, Quaid Avenue, Wah Cantt 47000, Pakistan
  • 9 Department of Clinical Pharmacy, Institute for Research and Medical Consultations (IRMC), Imam Abdulrahman Bin Faisal University, P.O. Box 31441, Dammam, Saudi Arabia
  • 10 H.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Bioorg Chem, 2020 01;95:103555.
PMID: 31911306 DOI: 10.1016/j.bioorg.2019.103555

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.

* Title and MeSH Headings from MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine.

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