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
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.
Corresponding Author(s):
LUO Xianjin,Email:luoxianjin@sjtu.edu.cn; SHE Yuanbin,Email:sheyb@bjut.edu.cn
引用本文:
. Design, synthesis, and antiviral properties of 2-aryl-1H-benzimidazole-4-carboxamide derivatives[J]. Frontiers of Chemical Engineering in China, 2009, 3(3): 305-309.
Xianjin LUO, Zhonglü ZHANG, Yutian YANG, Fei XUE, Naiyun XIU, Yuanbin SHE. Design, synthesis, and antiviral properties of 2-aryl-1H-benzimidazole-4-carboxamide derivatives. Front Chem Eng Chin, 2009, 3(3): 305-309.
Cheng J, Xie J T, Luo X J. Synthesis and antiviral activity against Coxsackie virus B3 of some novel benzimidazole derivatives. Bioorg Med Chem Lett , 2005, 15: 267-269 doi: 10.1016/j.bmcl.2004.10.087
2
Kristjan G, Richard S P, Aurora R L D. Preparation of (quinolinylaminoalkyl)-benzimidazole derivatives as chemokine receptor ligands with anti-HIV activity. WO2006023400
3
White A W, Almassy T, Calvert A H, Crutin N J, Griffin R J, Hostomsky Z, Maegley K, Newell D R, Srinivasan S, Golding B T. Resistance-modifying agents. 9. Synthesis and biological properties of benzimidazole inhibitors of the DNA repair enzyme poly(ADP-ribose) polymerase. J Med Chem , 2000, 43: 4084-4097 doi: 10.1021/jm000950v
4
Garuti L, Roberti M, Cermelli C. Synthesis and antiviral activity of some N-(benzenesulphonyl)-benzimidazoles. Bioorg Med Chem Lett , 1999, 9: 2525-2530 doi: 10.1016/S0960-894X(99)00429-1
5
Garuti L, Roberti M, Clercq E D. Synthesis and antiviral/antiproliferative activity of some N-sulphonyl-benzimidazoles. Bioorg Med Chem Lett , 2002, 12: 2707-2710 doi: 10.1016/S0960-894X(02)00535-8
6
Gilbert B E, Knight V. Biochemistry and clinical applications of ribavirin. Agents Chemother , 1986, 30: 201-205
7
Chapman E, Stephen H J. Preparation of phthalamic acids and their conversion into anthranilic acids. Chem Soc , 1925, 127: 1791-1797
8
Barkalow J H, Breting J, Gaede B J, Haight A R, Henry R, Kotecki B, Mei J, Pearl K B, Tedrow J S, Viswanath S K. Process Development for ABT-472, a Benzimidazole PARP Inhibitor. Organic Process Research and Development , 2007, 11: 693-698 doi: 10.1021/op7000194
9
William A D, Gordon W R, Bruce C B. Potential antitumor agents. 59. Structure-activity relationships for 2-phenylbenzimidazole-4-carboxamides, a new class of “minimal” DNA-intercalating agents which may not act via topoisomerase II. J Med Chem , 1990, 33: 814-819 doi: 10.1021/jm00164a054
