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Synthesis, biological activities, and molecular docking studies of 2-mercaptobenzimidazole based derivatives.

Authors :
Ali M
Ali S
Khan M
Rashid U
Ahmad M
Khan A
Al-Harrasi A
Ullah F
Latif A
Source :
Bioorganic chemistry [Bioorg Chem] 2018 Oct; Vol. 80, pp. 472-479. Date of Electronic Publication: 2018 Jun 30.
Publication Year :
2018

Abstract

A new series of N-acylhydrazone derivatives of 2-mercaptobenzimidazole (2-MBI) has been synthesized through S-alkylation with 1-bromotetradecane and N-alkylation with ethyl-2-chloroacetate. The resulting ester was synthetically modified through hydrazine hydrate to acyl hydrazide which was condensed with aromatic aldehydes to afford the title N-acylhydrazones (4-17). Chemical structures of the newly synthesized compounds have been confirmed through mass, FT-IR and <superscript>1</superscript> HNMR techniques. In vitro free radical scavenging and α-glucosidase inhibition activities of the compounds were investigated with reference to the standard ascorbic acid and acarbose, respectively. Amongst the target compounds, 13 showed the highest inhibition in DPPH scavenging assay (IC <subscript>50</subscript>  = 131.50 µM) and α-glucosidase inhibition potential (IC <subscript>50</subscript>  = 352 µg/ml). We extended our investigations to explore the mechanism of enzyme inhibition and conducted docking analysis by using Molecular Operating Environment (MOE 2016.08). A homology model for α-glucosidase was constructed and validated using Ramachandran plot. Docking studies were also carried out on human intestinal α-glucosidases. In view of the importance of the nucleus involved, the synthesized compounds might find extensive medicinal applications as reported in the literature.<br /> (Copyright © 2018 Elsevier Inc. All rights reserved.)

Details

Language :
English
ISSN :
1090-2120
Volume :
80
Database :
MEDLINE
Journal :
Bioorganic chemistry
Publication Type :
Academic Journal
Accession number :
29990895
Full Text :
https://doi.org/10.1016/j.bioorg.2018.06.032