Novel potent inhibitors of hepatitis C virus (HCV) NS3 protease with cyclic sulfonyl P3 cappings

Bioorganic and Medicinal Chemistry Letters

Volumn 19, Issue 4, 2009, Pages 1105-1109

  Chen, Kevin X ^a   Vibulbhan, Bancha ^a   Yang, Weiying ^a   Nair, Latha G ^a   Tong, Xiao ^a   Cheng, Kuo Chi ^a   Njoroge, F George ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

HCV; Ketoamide; Protease inhibitor; Serine protease

Indexed keywords

BENZENE DERIVATIVE; BICYCLO COMPOUND; NONSTRUCTURAL PROTEIN 3; SULFONE DERIVATIVE; SULFONYLUREA;

AREA UNDER THE CURVE; ARTICLE; DRUG POTENCY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; HEPATITIS C VIRUS; NONHUMAN; RAT; REPLICON; STRUCTURE ACTIVITY RELATION;

ADMINISTRATION, ORAL; ANIMALS; ANTIVIRAL AGENTS; COMBINATORIAL CHEMISTRY TECHNIQUES; DRUG DESIGN; HEPACIVIRUS; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONYLUREA COMPOUNDS; THIAZINES; VIRAL NONSTRUCTURAL PROTEINS;

HEPATITIS C VIRUS; RATTUS;

EID: 59649110618     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.12.111     Document Type: Article

References (38)

1. Cohen J. Science 285 (1999) 26
2. Alter M.J., Kruszon-Moran D., Nainan O.V., McQuillan G.M., Gao F., Moyer L.A., Kaslow R.A., and Margolis H.S. N. Engl. J. Med. 341 (1999) 556
3. Cuthbert J.A. Clin. Microbiol. Rev. 7 (1994) 505
4. Monto A., and Wright T.L. Semin. Oncol. (2001) 441
5. Neumann A.U., Lam N.P., Dahari H., Gretch D.R., Wiley T.E., Layden T.J., and Perelson A.S. Science 282 (1998) 103
6. Rosen H.R., and Gretch D.R. Mol. Med. Today 5 (1999) 393
7. Di Bisceglie A.M., McHutchison J., and Rice C.M. Hepatology 35 (2002) 224
8. Lindenbach B.D., and Rice C.M. Nature 436 (2005) 933
9. Kolykhalov A.A., Mihalik K., Feinstone S.M., and Rice C.M. J. Virol. 74 (2000) 2046
10. De Francesco R., and Migliaccio G. Nature 436 (2005) 953
11. Tan S.-L., He Y., Huang Y., and Gale Jr. M. Curr. Opin. Pharmacol. 4 (2004) 465
12. Malancona S., Colarrusso S., Ontoria J.M., Marchetti A., Poma M., Stansfield I., Laufer R., Marco A.D., Taliani M., Verdirame M., Gonzalez-paz O., Matassa V.G., and Narjes F. Bioorg. Med. Chem. Lett. 14 (2004) 4575
13. Llinas-Brunet M., Bailey M.D., Ghiro E., Gorys V., Halmos T., Poirier M., Rancourt J., and Goudreau N. J. Med. Chem. 47 (2004) 6584
14. Andrews D.M., Barnes M.C., Dowle M.D., Hind S.L., Johnson M.R., Jones P.S., Mills G., Patikis A., Pateman T.J., Redfern T.J., Ed Robinson J., Slater M.J., and Trivedi N. Org. Lett. 5 (2003) 4631
15. Zhang X. IDrugs 5 (2002) 154
16. Dymock B.W. Expert Opin. Emerg. Drugs 6 (2001) 13
17. Dymock B.W., Jones P.S., and Wilson F.X. Antivir. Chem. Chemother. 11 (2000) 79
18. Zhang R., Durkin J.P., and Windsor W.T. Bioorg. Med. Chem. Lett. 12 (2002) 1005
19. Ingallinella P., Fattori D., Altamura S., Steinkuhler C., Koch U., Cicero D., Bazzo R., Cortese R., Bianchi E., and Pessi A. Biochemistry 41 (2002) 5483
20. Beevers R., Carr M.G., Jones P.S., Jordan S., Kay P.B., Lazell R.C., and Raynham T.M. Bioorg. Med. Chem. Lett. 12 (2002) 641
21. For BILN-2061, see:. Lamarre D., Anderson P.C., Bailey M., Beaulieu P., Bolger G., Bonneau P., Bös M., Cameron D.R., Cartier M., Cordingley M.G., Faucher A.-M., Goudreau N., Kawai S.H., Kukolj G., Lagacé L., LaPlante S.R., Narjes H., Poupart M.-A., Rancourt J., Sentjens R.E., George T.S., Simoneau B., Steinmann G., Thibeault D., Tsantrizos Y.S., Weldon S.M., Yong C.-L., and Llinàs-Brunet M. Nature 426 (2003) 186
22. Tsantrizos Y.S., Bolger G., Bonneau P., Cameron D.R., Gordreau N., Kukolj G., LaPlante S.R., Llinas-Brunet M., Nar H., and Lamarre D. Angew. Chem. Int. Ed. 42 (2003) 1355
23. For VX-950, see:. Yip Y., Victor F., Lamar J., Johnson R., Wang Q., May G., John I., Yumibe N., Wakulchik M., Munroe J., and Chen S.-H. Bioorg. Med. Chem. Lett. 14 (2004) 5007
24. Perni, R. Presented at the Gordon Research Conference, New London, New Hampshire, August, 2005.
25. For SCH 503034, see:. Njoroge F.G., Chen K.X., Shih N.-Y., and Piwinski J.J. Acc. Chem. Res. 41 (2008) 50
26. Venkatraman S., Bogen S.L., Arasappan A., Bennett F., Chen K., Jao E., Liu Y.-T., Lovey R., Hendrata S., Huang Y., Pan W., Parekh T., Pinto P., Popov V., Pike R., Ruan S., Santhanam B., vibulbhan B., Wu W., Yang W., Yang W., Kong J., Liang X., Wong J., Liu R., Butkiewicz N., Chase R., Hart A., Agarwal S., Ingravallo P., Pichardo J., Kong R., Baroudy B., Malcolm B., Guo Z., Prongay A., Madision V., Broske L., Cui X., Cheng K.-C., Hsieh T.Y., Brisson J.-M., Prelusky D., Kormacher W., White R., Bogonowich-Knipp S., Pavlovsky A., Prudence B., Saksena A.K., Ganguly A., Piwinski J., Girijavallabhan V., and Njoroge F.G. J. Med. Chem. 49 (2006) 6074
27. Chen K.X., Njoroge F.G., Arasappan A., Venkatraman S., Vibulbhan B., Yang W., Parekh T., Pichardo J., Prongay A., Cheng K.-C., Butkiewicz N., Yao N., Madison V., and Girijavallabhan V. J. Med. Chem. 49 (2006) 995
28. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
29. Hughes D.L. Org. React. 42 (1992) 335
30. Mitsunobu O. Synthesis (1981) 1
31. Zhang R., Beyer B.M., Durkin J., Ingram R., Njoroge F.G., Windsor W.T., and Malcolm B.A. Anal. Biochem. 270 (1999) 268 The substrate Ac-DTEDVVP(Nva)-O-PAP was used in the present study.
32. Taremi S.S., Beyer B., Maher M., Yao N., Prosise W., Weber P.C., and Malcolm B. Protein Sci. 7 (1998) 2143
33. * and discussions, see: Morrison, J. F.; Walsh, C. T. In Meister, A., Ed.; Adv. Enzymol.; 1988; Vol. 61, pp 201-301.
34. Chung v., Carroll A.R., Gray N.M., Parry N.R., Thommes P.A., Viner K.C., and D'Souza E.A. Antimicrob. Agents Chemother. 49 (2005) 1381
35. Blight K.J., Kolykhalov A.A., and Rice C.M. Science 290 (2000) 1972
36. Lohmann V., Körner F., Koch J.-O., Herian U., Theilmann L., and Bartenschlager R. Science 285 (1999) 110
37. Yan Y., Li Y., Munshi S., Sardana V., Cole J.L., Sardana M., Steinkuehler C., Tomei L., De Francesco R., Kuo L.C., and Chen Z. Protein Sci. 7 (1998) 837
38. Di Marco S., Rizzi M., Volpari C., Walsh M.A., Narjes F., Colarusso S., De Francesco R., Matassa V.G., and Sollazzo M. J. Biol. Chem. 275 (2000) 7152