Glycine α-ketoamides as HCV NS3 protease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 13, Issue 6, 2003, Pages 1111-1114

  Han, Wei ^a   Hu, Zilun ^a   Jiang, Xiangjun ^a   Wasserman, Zelda R ^a   Decicco, Carl P ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; ANTIVIRUS AGENT; CARBOXYLIC ACID DERIVATIVE; GLYCINE DERIVATIVE; KETONE DERIVATIVE; PROTEINASE INHIBITOR;

ANTIVIRAL ACTIVITY; ARTICLE; DEPROTECTION REACTION; DRUG EFFICACY; DRUG POTENCY; ENZYME ACTIVE SITE; HEPATITIS C VIRUS; IC 50; OXIDATION;

HEPATITIS C VIRUS;

EID: 0037463788     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(03)00031-3     Document Type: Article

References (22)

1. Houghton, M. In Fields Virology, 3rd ed.; Raven: New York, 1996; p 1035.
2. Bartenschlager R. Antiviral Chem. Chemother. 8:1997;281.
3. (a) LaPlante S.R., Cameron D.R., Aubry N., Lefebvre S., Kukolj G., Maurice R., Thibeault D., Lamarre D., Llinàs-Brunet M. J. Biol. Chem. 274:1999;18618.
4. (b) DiMarco S., Rizzi M., Volpari C., Walsh M.A., Narjes F., Colarusso S., De Francesco R., Matassa V.G., Sollazzo M. J. Biol. Chem. 275:2000;7152.
5. (a) Kolykhalov A.A., Agapov E.V., Blight K.J., Mihalik K., Feinstone S.M., Rice C.M. Science. 277:1997;570.
6. (b) Kolykhalov A.A., Mihalik K., Feinstone S.M., Rice C.M. J. Virol. 74:2000;2046.
7. Bartenschlager R. J. Viral Hepatitis. 6:1999;165.
8. (a) Love R.A., Parge H.E., Wickersham J.A., Hostomsky Z., Habuka N., Moomaw E.W., Adachi T., Hostomska Z. Cell. 87:1996;331.
9. (b) Kim J.L., Morgenstern K.A., Lin C., Fox T., Dwyer M.D., Landro J.A., Chambers S.P., Markland W., Lepre C.A., O'Malley E.T., Harbeson J.A. Cell. 87:1996;343.
10. (c) Yao N., Reichert P., Taremi S.S., Prosise W.W., Weber P.C. Structure. 7:1999;1353.
11. (a) Han W., Hu Z.-L., Jiang X.-J., Decicco C.P. Bioorg. Med. Chem. Lett. 10:2000;711. and references therein
12. (b) Han, W.; Jiang, X.-J.; Hu, Z.-L.; Wasserman, Z. R.; Decicco, C. P. Abstract of Presentation, National Meeting of the American Chemical Society, San Diego, Apr. 2001; MEDI-119 and MEDI-121.
13. (a) Bennett J.M., Campbell A.D., Campbell A.J., Carr M.G., Dunsdon R.M., Greening J.R., Hurst D.N., Jennings N.S., Jones P.S., Jordan S., Kay P.B., O'Brien M.A., King-Underwood J., Raynham T.M., Wilkinson C.S., Wilkinson T.C.I., Wilson F.X. Bioorg. Med. Chem. Lett. 11:2001;355.
14. (b) Llinàs-Brunet M., Bailey M., Déziel R., Fazal G., Gorys V., Goulet S., Halmos T., Maurice R., Poirier M., Poupart M., Rancourt J., Thibeault D., Wernic D., Lamarre D. Bioorg. Med. Chem. Lett. 8:1998;2719.
15. Ingallinella P., Fattori D., Altamura S., Steinkühler C., Koch U., Cicero D., Bazzo R., Cortese R., Bianchi E., Pessi A. Biochemistry. 41:2002;5483.
16. The same assay conditions were used as described in ref 7a.
17. Binding mode for α-ketoacid has been reported: Colarusso S., Gerlach B., Koch U., Muraglia E., Conte I., Stansfield I., Matassa V.G., Narjes F. Bioorg. Med. Chem. Lett. 12:2002;705.
18. Ingallinella P., Altamura S., Bianchi E., Taliani M., Ingenito R., Cortese R., De Francesco R., Steinkühler C., Pessi A. Biochemistry. 37:1998;8906.
19. (a) Poupart M., Cameron D.R., Chabot C., Ghiro E., Goudreau N., Goulet S., Poirier M., Tsantrizos Y.S. J. Org. Chem. 66:2001;4743.
20. (b) Llinàs-Brunet M., Bailey M., Fazal G., Ghiro E., Gorys V., Goulet S., Halmos T., Maurice R., Poirier M., Poupart M., Rancourt J., Thibeault D., Wernic D., Lamarre D. Bioorg. Med. Chem. Lett. 10:2000;2267.
21. Narjes F., Koehler K.F., Koch U., Gerlach B., Colarusso S., Steinkühler C., Brunetti M., Altamura S., De Francesco R., Matassa V.G. Bioorg. Med. Chem. Lett. 12:2002;701.
22. Wasserman H.H., Ho W.B. J. Org. Chem. 59:1994;4364.