Difluoromethyleneketone retroamide, a versatile concept of inactivation of proteolytic enzymes

Tetrahedron

Volumn 52, Issue 1, 1996, Pages 305-318

  Schirlin, D ^a   Baltzer, S ^a   Altenburger, J M ^a   Tarnus, C ^a   Remy, J M ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; ENZYME INHIBITOR; PROTEINASE; PROTEINASE INHIBITOR; PSEUDOPEPTIDE; THROMBIN;

CONFERENCE PAPER; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS 1; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0029655472     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00896-G     Document Type: Article

References (29)

1. Abeles, R.H.; Alston, T.A. J. Biol. Chem. 1990, 265, 16705.
2. Gelb, M.H.; Svaren, J.P.; Abeles, R.H. Biochemistry 1985, 24, 1813.
3. For a review see: Greenlee, W.J. Medicinal Research Review 1990, 10, 173.
4. Peet, N.P.; Burkhart, J.P.; Angelastro, M.R.; Giroux, E.L.; Mehdi, S.; Bey, P.; Kolb, M.; Neises, B.; Schirlin, D. J. Med. Chem. 1990, 33, 394.
5. Schirlin, D.; Baltzer, S.; Van Dorsselaer, V.; Weber, F.; Weill, C.; Altenburger, J.M.; Neises, B.; Flynn, G.; Remy, J.M.; Tarnus, C. Bioorg. Med. Chem. Lett. 1993, 3, 253.
6. Robinson, R.P.; Donahue, K.M. J. Org. Chem. 1992, 57, 7309.
7. 7a. Imperiali, B.; Abeles, R.H.; Biochemistry 1986, 25, 3760.
8. b. Imperiali, B.; Abeles, R.H. Biochemistry 1987, 26, 4474.
9. 8a. Damon, D.B.; Hoover, D.J. J. Am. Chem. Soc. 1990, 112, 6439.
10. b. Hong, W.; Dong, L.; Cai, Z.; Titmas, R. Tetrahedron Lett. 1992, 33, 741.
11. 19F NMR and X ray crystallography.
12. Schirlin, D.; Baltzer, S.; Altenburger, J.M. Tetrahedron Lett.1988, 29, 3687.
13. Tarnus, C.; Jung, M.J.; Remy J.M.; Baltzer, S.; Schirlin, D.G. FEBS Lett. 1989, 249, 47.
14. Altenburger, J.M.; Schirlin, D. Tetrahedron Lett.1991, 32, 7255.
15. Mjalli, A.M.M.; Chapman, K.J.; MacCoss, M. Bioorg. Med. Chem. Lett. 1993, 3, 2693.
16. Angelastro, M.R.; Mehdi, S.; Burkhart, J.P.; Peet, N.P.; Bey, P. J. Med. Chem.1990, 33, 11.
17. Schirlin, D.; Jung, M.J. European Patent Application 88 EP 275-101A.
18. Sham, H.L.; Wideburg, N.E.; Spanton, S.G.; Kohlbrenner, W.E.; Betebemer, D.A.; Kempf, D.J.; Norbeck, D.W.; Plattner, J.J.; Erickson, J.W. J. Chem. Soc. Chem. Commun. 1991, 110.
19. 17a. Mancuso, A.J.; Huang, S.L.; Swern, D.J. J.Org.Chem.1978, 43, 2480.
20. b. Pfitzner, K.E.; Moffatt, J.G. J. Am. Chem. Soc. 1965, 87, 5661.
21. Dess, D.B.; Martin, J.C. J. Org. Chem. 1983, 48, 4155.
22. Schirlin, D.; Tarnus, C.; Baltzer, S.; Remy, J.M. Bioorg. Med. Chem. Lett. 1992, 2, 651.
23. Goodman, M.; Chorev, M. Acc. Chem. Res. 1979, 12, 1.
24. West, M.L.; Fairlie, D.P. Trends Pharmacol. Sci. 1995, 16, 67.
25. See for instance: Dreyer, G.B.; Metcalf, B.W.; Tomaszek, T.A. Jr.; Carr, T.J.; Chandler, A.C. III; Hyland, L.; Fakhoury, S.A.; Magaard, V.W.; Moore, M.L.; Strickler, J.E.; Debouck, C., Meek, T.D. Proc. Natl. Acad. Sci. USA 1989, 86, 9752.
26. Skilaes, J.W.; Miao, C.; Sorcek, R.; Jacober, S.; Mui, P.W.; Chow, G.; Weldon, S.M.; Possanza, G.; Skoog, M.; Keirns, J.; Letts, G. and Rosenthal, A.S. J. Med. Chem. 1992, 35, 4795.
27. Darke, P.L.; Nutt, R.F.; Brady, S.F.; Garsky, V.M.; Ciccarone, T.M.; Leu, C.T.; Lumma, P.K.; Freidinger, R.M.; Veber, D.F.; Sigal, I.S. Biochem. Biophys. Res. Commun. 1988, 156, 297.
28. Bernstein, P.R.; Kosmider, B.J.; Vacek, E.P.; Veale, C.A.; Gomes, B.C. Bioorg Med. Chem. Lett. 1994, 4, 2175.
29. Neises, B.; Tarnus, C. and Remy J.M. Unpublished results.