Trifluoroethylamines as amide isosteres in inhibitors of cathepsin K

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 21, 2005, Pages 4741-4744

  Black, W Cameron ^a   Bayly, Christopher I ^a   Davis, Dana E ^c   Desmarais, Sylvie ^a   Falgueyret, Jean Pierre ^a   Léger, Serge ^a   Chun, Sing Li ^a   Massé, Frédéric ^a   McKay, Daniel J ^a   Palmer, James T ^c   Percival, M David ^a   Robichaud, Joël ^a   Tsou, Nancy ^b   Zamboni, Robert ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

^c CELERA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CATHEPSIN K INHIBITOR; DIPEPTIDE; ETHYLAMINE; GLYCINE; NITROGEN;

ARTICLE; DRUG POTENCY; DRUG SELECTIVITY; HYDROGEN BOND; METABOLISM;

AMIDES; CATHEPSINS; DIPEPTIDES; ETHYLAMINES; HUMANS; HYDROGEN BONDING; INHIBITORY CONCENTRATION 50; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 25144461176     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.07.071     Document Type: Article

References (19)

1. N. Venkatesan, and B.H. Kim Curr. Med. Chem. 9 2002 2243
2. J. Gante Angew. Chem. Int. Ed. Engl. 33 1994 1699
3. A. Volonterio, S. Bellosta, F. Bravin, M.C. Bellucci, L. Bruché, G. Colombo, L. Malpezzi, S. Mazzini, S.V. Meille, M. Meli, C. Ramírez de Arellano, and M. Zanda Chem. Eur. J. 9 2003 4510
4. M. Molteni, A. Volonterio, and M. Zanda Org. Lett. 5 2003 3887
5. A. Volonterio, P. Bravo, and M. Zanda Org. Lett. 2 2000 1827
6. S. Herrero, M.L. Suárez-Gea, R. González-Muñiz, M.T. GarcIÍa-López, R. Herranz, S. Ballaz, A. Barber, A. Fortuño, and J. Del RIÍo Bioorg. Med. Chem. Lett. 7 1997 855
7. Palmer, J. T.; Bryant, C.; Wang, D. -X.; Davis, D. E.; Setti, E. L.; Rydzewski, R. M.; Venkatraman, S.; Tian, Z.-Q.; Burrill, L. C.; Mendonca, R. V.; Springman, E.; McCarter, J.; Chung, T.; Cheung, H.; McGrath, M.; Somoza, J.; Enriquez, P.; Yu, Z. W.; Strickley, R. M.; Liu, L.; Venuti, M. C.; Percival, M. D.; Falgueyret, J. -P.; Prasit, P.; Oballa, R.; Riendeau, D.; Young, R. N.; Wesolowski, G.; Rodan, S. B.; Johnson, C.; Kimmel, D. B.; Rodan, G. J. Med. Chem. 2005 in press.
8. M.E. McGrath, J.L. Klaus, M.G. Barnes, and D. Bromme Nat. Struct. Biol. 4 1997 105 109
9. M.E. McGrath, P.A. Sprengeler, C.M. Hill, V. Martichonok, H. Cheung, J.R. Somoza, J.T. Palmer, and J.W. Janc Biochemistry 42 2003 15018
10. J. Robichaud, R. Oballa, P. Prasit, J.-P. Falgueyret, M.D. Percival, G. Wesolowski, S.B. Rodan, D. Kimmel, C. Johnson, C. Bryant, S. Venkatraman, E. Setti, R. Mendoca, and J.T. Palmer J. Med. Chem. 46 2003 3709
11. J. Robichaud, C. Bayly, R. Oballa, P. Prasit, C. Mellon, J.-P. Falgueyret, M.D. Percival, G. Wesolowski, and S.B. Rodan Bioorg. Med. Chem. Lett. 14 2004 4291
12. A. Ishii, K. Higashiyama, and K. Mikami Synlett 1997 1381
13. F. Gosselin, A. Roy, P.D. O'Shea, C. Chen, and R.P. Volante Org. Lett. 6 2004 641
14. F. Gosselin, P.D. O'Shea, S. Roy, C. Chen, R.A. Reamer, C. Chen, and R.P. Volante Org. Lett. 7 2005 355
15. M. Zhao, J. Li, Z. Song, D. Desmond, D.M. Tschaen, E.J.J. Grabowski, and P.J. Reider Tetrahedron Lett. 39 1998 5323
16. 50s below 5 pM cannot be determined.
17. Crystallographic data (excluding structure factors) for the structures in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 274083 for 11. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK [e-mail: deposit@ccdc.cam.ac.uk].
18. Advanced Chemistry Development, Inc., Toronto, Canada; v6.00.
19. J.-P. Falgueyret, W.C. Black, W. Cromlish, S. Desmarais, S. Lamontagne, C. Mellon, D. Riendeau, S. Rodan, P. Tawa, G. Wesolowski, K.E. Bass, S. Venkatraman, and M.D. Percival Anal. Biochem. 335 2004 218