Coumarins hinged directly on benzimidazoles and their ribofuranosides to inhibit hepatitis C virus

European Journal of Medicinal Chemistry

Volumn 63, Issue , 2013, Pages 290-298

  Tsay, Shwu Chen ^a   Hwu, Jih Ru ^a,b   Singha, Raghunath ^b   Huang, Wen Chieh ^b   Chang, Yung Hsiung ^b   Hsu, Ming Hua ^b   Shieh, Fa Kuen ^a   Lin, Chun Cheng ^b   Hwang, Kuo Chu ^b   Horng, Jia Cherng ^b   De Clercq, Erik ^c   Vliegen, Inge ^c   Neyts, Johan ^c  

^a NATIONAL CENTRAL UNIVERSITY   (Taiwan)

^b NATIONAL TSING HUA UNIVERSITY   (Taiwan)

^c REGA INSTITUTE FOR MEDICAL RESEARCH   (Belgium)

Author keywords

Anti HCV; Benzimidazole; Coumarin; Hinged hybride; Ribofuranoside

Indexed keywords

3 (5' METHYLBENZIMIDAZOL 2' YL) 4 METHYLCOUMARIN; 3 (5' METHYLBENZIMIDAZOL 2' YL)COUMARIN; 8 METHOXY 3 (5' METHYLBENZIMIDAZOL 2' YL)COUMARIN; ANTIVIRUS AGENT; BENZIMIDAZOLE DERIVATIVE; COUMARIN DERIVATIVE; FUNCTIONAL GROUP; NUCLEOSIDE; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; HEPATITIS C VIRUS; HYBRID; STRUCTURE ACTIVITY RELATION; VIRUS INHIBITION; VIRUS REPLICATION;

ANTIVIRAL AGENTS; BENZIMIDAZOLES; CELL LINE, TUMOR; COUMARINS; DOSE-RESPONSE RELATIONSHIP, DRUG; FURANS; GLYCOSIDES; HEPACIVIRUS; HUMANS; MASS SPECTROMETRY; MODELS, CHEMICAL; MOLECULAR STRUCTURE; PENTOSES; SPECTROSCOPY, FOURIER TRANSFORM INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; VIRUS REPLICATION;

EID: 84874930050     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2013.02.008     Document Type: Article

References (44)

1. G.M. Lauer, and B.D. Walker N. Engl. J. Med. 345 2001 41 52
2. E.H. Sklan, P. Charuworn, P.S. Pang, and J.S. Glenn Nat. Rev. Gastroenterol. Hepatol. 6 2009 217 227
3. P. Roingeard, and C. Hourioux J. Viral Hepatol. 15 2008 157 164
4. F. Penin, J. Dubuisson, F.A. Rey, D. Moradpour, and J.-M. Pawlotsky Hepatology 39 2004 5 19
5. L. Delang, L. Coelmont, and J. Neyts Viruses 2 2010 826 866
6. E. Thomas, J.J. Feld, Q. Li, Z. Hu, M.W. Fried, and T.J. Liang Hepatology 53 2011 32 41
7. M. Bretner Acta Biochim. Pol. 52 2005 57 70
8. N.N. Zein J. Hepatol. 42 2005 315 322
9. J. Schlütter Nature 474 2011 S5 S7
10. P.Y. Kwo, E.J. Lawitz, J. McCone, E.R. Schiff, J.M. Vierling, D. Pound, M.N. Davis, J.S. Galati, S.C. Gordon, N. Ravendhran, L. Rossaro, F.H. Anderson, I.M. Jacobson, R. Rubin, K. Koury, L.D. Pedicone, C.A. Brass, E. Chaudhri, and J.K. Albrecht Lancet 316 2010 705 716
11. J.G. McHutchison, G.T. Everson, S.C. Gordon, I.M. Jacobson, M. Sulkowski, R. Kauffman, L. McNair, J. Alam, and A.J. Muir New Engl. J. Med. 360 2009 1827 1838
12. N. Mani, B.G. Rao, T.L. Kieffer, and A.D. Kwong Antiviral drug strategies E. De Clercq, Recent Progress in the Development of HCV Protease Inhibitors 2011 Wiley-VCH Weinheim, Germany 307 328
13. R. Liu, Z. Huang, M.G. Murray, X. Guo, and G. Liu J. Med. Chem. 54 2011 5747 5768
14. M. Andrzejewska, L. Y'epez-Mulia, R. Cedillo-Rivera, A. Tapia, L. Vilpo, J. Vilpo, and Z. Kazimierczuk Eur. J. Med. Chem. 37 2002 973 978
15. F. Gümüs, Ö. Algül, G. Eren, H. Eroǧlu, N. Diril, S. Gür, and A. Özkul Eur. J. Med. Chem. 38 2003 473 480
16. C. Ito, M. Itoigawa, Y. Mishina, V.C. Filho, F. Enjo, H. Tokuda, H. Nishino, and H. Furukawa J. Nat. Prod. 66 2003 368 371
17. N.-H. Nam, Y. Kim, Y.-J. You, D.-H. Hong, H.-M. Kim, and B.-Z. Ahn Bioorg. Med. Chem. Lett. 12 2002 2345 2348
18. A. Kamal, P. Ramulu, O. Srinivas, G. Ramesh, and P.P. Kumar Bioorg. Med. Chem. Lett. 14 2004 4791 4794
19. P.M.S. Chauhan, C.J.A. Martins, and D.C. Horwell Bioorg. Med. Chem. 13 2005 3513 3518
20. S. Demirayak, U.A. Mohsen, and A.C. Karaburun Eur. J. Med. Chem. 37 2002 255 260
21. L. Garuti, M. Roberti, M. Malagoli, T. Rossi, and M. Castelli Bioorg. Med. Chem. Lett. 10 2000 2193 2195
22. E. Lukevics, P. Arsenyan, I. Shestakova, I. Domracheva, A. Nesterova, and O. Pudova Eur. J. Med. Chem. 36 2001 507 515
23. V.D. Handratta, T.S. Vasaitis, V.C.O. Njar, L.K. Gediya, R. Kataria, P. Chopra, D. Newman Jr., R. Farquhar, Z. Guo, Y. Qiu, and A.M.H. Brodie J. Med. Chem. 48 2005 2972 2984
24. P.N. Reddy, Y.T. Reddy, M.K. Rao, and B. Rajitha Heterocycl. Commun. 9 2003 647 652
25. E.S.M.A. Yakout Egypt. J. Chem. 45 2003 1029 1042
26. S. Lee, K. Sivakumar, W.-S. Shin, F. Xie, and Q. Wang Bioorg. Med. Chem. Lett. 16 2006 4596 4599
27. P.L. Beaulieu, Y. Bousquet, J. Gauthier, J. Gillard, M. Marquis, G. McKercher, C. Pellerein, S. Valois, and G. Kukolj J. Med. Chem. 47 2004 6884 6892
28. G. McKercher, P.L. Beaulieu, D. Lamarre, S. LaPlante, S. Lefebvre, C. Pellerin, L. Thauvette, and G. Kukolj Nucleic Acids Res. 32 2004 422 431
29. S. Hirashima, T. Suzuki, T. Ishida, S. Noji, S. Yata, I. Ando, M. Komatsu, S. Ikeda, and H. Hashimoto J. Med. Chem. 49 2006 4721 4736
30. 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 1863
31. K.-S. Yeung, N.A. Meanwell, Z. Qiu, D. Hernandez, S. Zhang, F. McPhee, S. Weinheimer, J.M. Clark, and J.W. Janc Bioorg. Med. Chem. Lett. 11 2001 2355 2359
32. J. François, A. Raymond, WO Patent 128344 A1, 2008.
33. B. Xu, Q. Zhu, H.-J. Cho, R. Fathi, Z. Yang, A. Sandrasagra, Y. Liu, U.S. Patent 0,223,783 A1, 2006.
34. J. Wu, Z. Yang, R. Fathi, Q. Zhu, U.S. Patent 0,180,950 A1, 2004.
35. H.-P. Hsieh, T.-A. Hsu, J.-Y. Yeh, J.-T. Horng, S.-R. Shih, S.-Y. Chang, Y.-S. Chao, U.S. Patent 0,312,406 A1, 2009.
36. J.R. Hwu, R. Singha, S.C. Hong, Y.H. Chang, A.R. Das, I. Vliegen, E. De Clercq, and J. Neyts Antiviral Res. 77 2008 157 162
37. J. Neyts, E. De Clercq, R. Singha, Y.H. Chang, A.R. Das, S.K. Chakraborty, S.C. Hong, S.-C. Tsay, M.-H. Hsu, and J.R. Hwu J. Med. Chem. 52 2009 1486 1490
38. J.R. Hwu, S.-Y. Lin, S.-C. Tsay, E. De Clercq, P. Leyssen, and J. Neyts J. Med. Chem. 54 2011 2114 2126
39. A.I. Khodair, N.A. Al-Masoudi, and J.-P. Gesson Nucleosides, Nucleotides Nucleic Acids 22 2003 2061 2076
40. P. Bhan, A. Bhan, M. Hong, J.G. Hartwell, J.M. Saunders, and G.D. Hoke Nucleic Acids Res. 25 1997 3310 3317
41. J. Parsch, and J.W. Engels J. Am. Chem. Soc. 124 2002 5664 5672
42. T. Chandra, and K.L. Brown Tetrahedron Lett. 46 2005 8617 8619
43. J. Paeshuyse, A. Kaul, E. De Clercq, B. Rosenwirth, J.-M. Dumont, P. Scalfaro, R. Bartenschlager, and J. Neyts Hepatology 43 2006 761 770
44. V. Lohmann, F. Korner, J. Koch, U. Herian, L. Theilmann, and R. Bartenschlager Science 285 1999 110 113