Design, synthesis, and antiviral properties of 2-aryl-1H-benzimidazole-4-carboxamide derivatives

doi:10.1007/s11705-009-0021-z

Front Chem Eng Chin

2009, Vol. 3

Issue (3) : 305-309 https://doi.org/10.1007/s11705-009-0021-z

RESEARCH ARTICLE

Design, synthesis, and antiviral properties of 2-aryl-1H-benzimidazole-4-carboxamide derivatives

Xianjin LUO¹(

), Zhonglü ZHANG¹, Yutian YANG¹, Fei XUE¹, Naiyun XIU², Yuanbin SHE³(

)

1. School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, China; 2. Schools of Life Science and Environmental Science, Shanghai Normal University, Shanghai 200234, China; 3. Institute of Green Chemistry and Fine Chemicals, Beijing University of Technology, Beijing 100022, China

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Abstract

A series of new benzimidazole derivatives were designed and synthesized. Their chemical structures were testified by ¹H NMR, infrared spectroscopy (IR), mass spectrography (MS), and elemental analysis. Their potent antiviral properties indicated the prospect of new drugs. Compound 13, 16, 18, 19, 21, 22, and 23 were identified as novel antivirus with much better selective activity and inhibitory activity than the comparable ribavirin against Coxsackie virus B₃ in VERO cells.

Keywords benzimidazole coxsackie virus B₃ antiviral properties

Corresponding Author(s): LUO Xianjin,Email:luoxianjin@sjtu.edu.cn; SHE Yuanbin,Email:sheyb@bjut.edu.cn

Issue Date: 05 September 2009

Cite this article:

Xianjin LUO,Zhonglü ZHANG,Yutian YANG, et al. Design, synthesis, and antiviral properties of 2-aryl-1H-benzimidazole-4-carboxamide derivatives[J]. Front Chem Eng Chin, 2009, 3(3): 305-309.

URL:

https://academic.hep.com.cn/fcse/EN/10.1007/s11705-009-0021-z
https://academic.hep.com.cn/fcse/EN/Y2009/V3/I3/305

Fig.1 General structure of synthesized compounds

Fig.2 Reagents and conditions: (a) NH(aq), 70°C; (b) KOH, Br, HO, 80°C; (c) NaOH, CHOH, Ranney Ni, NH×HO, reflux

Tab.1 Yields of compounds -

Fig.3 Reagents and conditions: (d) CHOH, Cu(AcO), reflux, then NaS; (e) CHOH, KFe(CN), reflux; (f) SOCl, reflux; (g) RNH, r.t

Tab.2 Activity of benzimidazole derivatives against Coxsackie virus B in VERO cells

Tab.3 Activity of benzimidazole derivatives against Coxsackie virus B in VERO cells

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