Design and synthesis of novel benzimidazole derivatives as inhibitors of hepatitis B virus

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 14, 2010, Pages 5048-5055

  Luo, Yu ^a   Yao, Jia Ping ^a   Yang, Li ^b   Feng, Chun Lan ^b   Tang, Wei ^b   Wang, Gui Feng ^b   Zuo, Jian Pin ^b   Lu, Wei ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Anti HBV activity; Benzimidazoles

Indexed keywords

1 BENZYL 2 [2 (1 METHYL 1H PYRROL 2 YL)ETHYL] 1H BENZOIMIDAZOLE; ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; LAMIVUDINE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HEPATITIS B VIRUS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTIVIRAL AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; CELL SURVIVAL; HEPATITIS B; HEPATITIS B VIRUS; HUMANS; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS B VIRUS;

EID: 77955337993     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.05.076     Document Type: Article

References (36)

1. E.E. Mast, M.J. Alter, and H.S. Margolis Vaccine 1999 1730
2. A. Regev, and E.R. Schiff Adv. Int. Med. 46 2001 107
3. W.C. Maddrey Clin. Lab. 47 2001 51
4. D.K. Wong, A.M. Cheung, O.K. Naylor, A.S. Detsky, and J. Heathcote Ann. Int. Med. 119 1993 312
5. G.A. Tipples, M.M. Ma, K.P. Fischer, V.G. Bain, N.M. Kneteman, and D.L.J. Tyrrell Hepatology 24 1996 714
6. K. Sekiya, H. Takashima, N. Ueda, N. Kamiya, S. Yuasa, Y. Fujimura, and M. Ubasawa J. Med. Chem. 45 2002 3138
7. S. Hirashima, T. Suzuuki, T. Ishida, S. Noji, S. Yata, I. Ando, M. Komatsu, S. Ikeda, and H. Hashimoto J. Med. Chem. 49 2006 4721
8. Z. Lv, C. Sheng, T. Wang, Y. Zhang, J. Liu, J. Feng, H. Sun, H. Zhong, C. Niu, and K. Li J. Med. Chem. 53 2010 660
9. G.-F. Wang, L.-P. Shi, Y.-D. Ren, Q.-F. Liu, H.-F. Liu, R.-J. Zhang, Z. Li, F.-H. Zhu, P.-L. He, W. Tang, P.-Z. Tao, C. Li, W.-M. Zhao, and J.-P. Zuo Antiviral Res. 83 2009 186
10. H.-J. Chen, W.-L. Wang, G.-F. Wang, L.-P. Shi, M. Gu, Y.-D. Ren, L.-F. Hou, P.-L. He, F.-H. Zhu, X.-G. Zhong, W. Tang, J.-P. Zuo, and F.-J. Nan ChemMedChem 3 2008 1316
11. K. Deres, C.H. Schroder, A. Paessens, S. Goldmann, H.J. Hacker, O. Weber, T. Kramer, U. Niewohner, U. Pleiss, J. Stoltefuss, E. Graef, D. Koletzki, R.N. Masantschek, A. Reimann, R. Jaeger, R. Groβ, B. Beckermann, K.H. Schlemmer, D. Haebich, and H. Rubsamen-Waigmann Science 299 2003 893
12. R.B. Perni, S.C. Conway, S.K. Ladner, K. Zaifert, M.J. Otto, and R.W. King Bioorg. Med. Chem. Lett. 10 2000 2687
13. J.S. Lee, H.S. Shim, Y.K. Park, S.J. Park, J.S. Shin, W.Y. Yang, H.D. Lee, W.J. Park, Y.H. Chung, and S.W. Lee Bioorg. Med. Chem. Lett. 12 2002 2715
14. H. Chai, Y. Zhao, C. Zhao, and P. Gong Bioorg. Med. Chem. 14 2006 911
15. P.P. Seth, A. Miyaji, E.A. Jefferson, K.A. Sannes-Lowery, S.A. Osgood, S.S. Propp, R. Ranken, C. Massire, R. Sampath, D.J. Ecker, E.E. Swayze, and R.H. Griffey J. Med. Chem. 48 2005 7099
16. S. Ozden, D. Atabey, S. Yildiz, and H. Goker Bioorg. Med. Chem. 13 2005 1587
17. P.L. Beaulieu, M. Bos, Y. Bousquet, P. DeRoy, G. Fazal, J. Gauthier, J. Gillard, S. Goulet, G. McKercher, M.A. Poupart, S. Valois, and G. Kukolj Bioorg. Med. Chem. Lett. 14 2004 967
18. J.S. Kim, B. Gatto, C. Yu, A. Liu, and E.J. LaVoie J. Med. Chem. 39 1996 992
19. Y.F. Li, G.F. Wang, P.L. He, W.G. Huang, F.H. Zhu, H.Y. Gao, W. Tang, Y. Luo, C.L. Feng, L.P. Shi, Y.D. Ren, W. Lu, and J.P. Zuo J. Med. Chem. 49 2006 4790
20. L. Garuti, M. Roberti, T. Rossi, C. Cermelli, M. Portolani, M. Malagoli, and M. Castelli Anti-Cancer Drug Des. 13 1998 397
21. T. Ishida, T. Suzuki, S. Hirashima, K. Mizutani, A. Yoshida, I. Ando, S. Ikeda, T. Adachi, and H. Hashimoto Bioorg. Med. Chem. Lett. 16 2006 1859
22. P.L. Beaulieu, Y. Bousquet, J. Gauthier, J. Gillard, M. Marquis, G. McKercher, C. Pellerin, S. Valois, and G. Kukolj J. Med. Chem. 47 2004 6884
23. L. Poitout, V. Brault, C. Sackur, S. Bernetiere, J. Camara, P. Plas, and P. Roubert Bioorg. Med. Chem. Lett. 17 2007 4464
24. K. Starcevic, M. Kralj, K. Ester, I. Sabol, M. Grce, K. Pavelic, and G. Karminski-Zamola Bioorg. Med. Chem. 15 2007 4419
25. H. Zellner, and G. Zellner Helv. Chim. Acta 49 1966 913
26. R.L. Dannley, and A. Grava Can. J. Chem. 43 1965 3377
27. E.J. Jacobsen, L.S. Stelzer, K.L. Belonga, D.B. Carter, W.B. Im, V.H. Sethy, A.H. Tang, P.F. VonVoigtlander, and J.D. Petke J. Med. Chem. 39 1996 3820
28. R. Chesworth, M.D. Wessel, L. Heyden, F.M. Mangano, M. Zawistoski, L. Gegans, D. Galluzzo, B. Lefker, K.O. Cameron, J. Tickner, B. Lu, T.A. Castleberry, D.N. Petersen, A. Brault, P. Perry, O. Ng, T.A. Owen, L. Pan, H.Z. Ke, T.A. Brown, D.D. Thompson, and P. DaSilva-Jardine Bioorg. Med. Chem. Lett. 15 2005 5562
29. R. Lin, P.J. Connolly, Y. Lu, G. Chiu, S. Li, Y. Yu, S. Huang, X. Li, S.L. Emanuel, S.A. Middleton, R.H. Gruninger, M. Adams, A.R. Fuentes-Pesquera, and L.M. Greenberger Bioorg. Med. Chem. Lett. 17 2007 4297
30. G. Semple, P.J. Skinner, M.C. Cherrier, P.J. Webb, C.R. Sage, S.Y. Tamura, R.P. Chen, J.G. Richman, and D.T. Connolly J. Med. Chem. 49 2006 1227
31. J. Neres, P. Bonnet, P.N. Edwards, P.L. Kotian, A. Buschiazzo, P.M. Alzari, R.A. Bryce, and K.T. Douglas Bioorg. Med. Chem. 15 2007 2106
32. 13a was previously reported in the following patent. Jorgensen, W.; Bucala, R. J. W.O. Patent 2,010,021,693.
33. M.H. Palmer, D.S. Leitch, and C.W. Greenhalgh Tetrahedron 34 1978 1015
34. T. Mosmann J. Immunol. Methods 65 1983 55
35. Z.S. Yang, W.L. Zhou, Y. Sui, J.X. Wang, J.M. Wu, Y. Zhou, Y. Zhang, P.L. He, J.Y. Han, W. Tang, Y. Li, and J.P. Zuo J. Med. Chem. 48 2005 4608
36. Q.L. Wu, Y.F. Fu, W.L. Zhou, J.X. Wang, Y.H. Feng, J. Liu, J.Y. Xu, P.L. He, R. Zhou, W. Tang, G.F. Wang, Y. Zhou, Y.F. Yang, J. Ding, X.Y. Li, X.R. Chen, C. Yuan, B.R. Lawson, and J.P. Zuo J. Pharmacol. Exp. Ther. 313 2005 705