期刊
BIOORGANIC CHEMISTRY
卷 80, 期 -, 页码 472-479出版社
ACADEMIC PRESS INC ELSEVIER SCIENCE
DOI: 10.1016/j.bioorg.2018.06.032
关键词
Benzimidazole; Benzimidazole-2-thiol; Hydrazone Schiff's bases; Antioxidant activity; alpha-Glucosidase activity; Molecular docking
资金
- HEC (Higher Education Commission) [20-2892]
- HEC [5291/Federal/NRPU/RD/HEC/2016]
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)-H-1 techniques. In vitro free radical scavenging and alpha-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 (IC50 = 131.50 mu M) and alpha-glucosidase inhibition potential (IC50 = 352 mu g/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 a-glucosidase was constructed and validated using Ramachandran plot. Docking studies were also carried out on human intestinal alpha-glucosidases. In view of the importance of the nucleus involved, the synthesized compounds might find extensive medicinal applications as reported in the literature.
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