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

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ID: 98853
2018
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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 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 = 131.50 µM) and α-glucosidase inhibition potential (IC = 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.
Reference Key
ali2018synthesisbioorganic Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Ali, Mumtaz;Ali, Sardar;Khan, Momin;Rashid, Umer;Ahmad, Manzoor;Khan, Ajmal;Al-Harrasi, Ahmed;Ullah, Farhat;Latif, Abdul;
Journal Bioorganic chemistry
Year 2018
DOI
S0045-2068(18)30395-X
URL
Keywords
molecular docking antioxidant activity benzimidazole benzimidazole-2-thiol hydrazone schiff′s bases α-glucosidase activity

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