Structure-based design of functionalized 2-substituted and 1,2-disubstituted benzimidazole derivatives and their in vitro antibacterial efficacy

Journal of Advanced Research

Shade J. Olorunshola¹  Olayinka O. Ajani²  Olayinka O. Tolu-Bolaji²  Damilola V. Aderohunmu²  Yuxia Zhao³ 

[1] Department of Biological Sciences, C.S.T., Covenant University, Canaanland, km 10, Idiroko Road, P.M.B. 1023, Ota, Ogun State, Nigeria;Department of Chemistry, C.S.T., Covenant University, Canaanland, km 10, Idiroko Road, P.M.B. 1023, Ota, Ogun State, Nigeria;Technical Institute of Physics and Chemistry, CAS, No 29, Zhongguancun East Road, Haidian District, Beijing 100190, China;

关键词: Benzimidazole;    Antibacterial;    Activity index;    Cycloaddition;    Spectroscopy;   

DOI  :  10.1016/j.jare.2017.09.003

来源: DOAJ

【 摘 要 】

The aim of this present study was to synthesize 2-substituted and 1,2-disubstituted benzimidazole derivatives to investigate their antibacterial diversity for possible future drug design. The structure-based design of precursors 2-(1H-benzimidazol-2-yl)aniline 1, 2-(3,5-dinitro phenyl)-1H-benzimidazole 3 and 2-benzyl-1H-benzimidazole 5 were achieved by the condensation reaction of o-phenylenediamine with anthranilic acid, 3,5-dinitrophenylbenzoic acid, and phenylacetic acid, respectively. The precursors 1, 3 and 5, upon reaction with six different electrophile-releasing agents, furnished the corresponding 2-substituted benzimidazole, 2a-f and 1,2-disubstituted benzimidazole derivatives 4a-f and 6a-f, respectively. The structural identity of the targeted compounds was authenticated by elemental analytical data and spectral information from FT-IR, UV, 1H, and 13C NMR. The outcome of the findings from the in vitro screening unveiled 2-benzyl-1-(phenylsulfonyl)-1H-benzimidazole 6b as the most active derivative with lowest MIC value of 15.63 µg/mL.

【 授权许可】

Unknown