4-Aminophenoxyacetic acids as a novel class of reversible cathepsin K inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 16, Issue 6, 2006, Pages 1502-1505

  Shinozuka, Tsuyoshi ^a   Shimada, Kousei ^a   Matsui, Satoshi ^a   Yamane, Takahiro ^a   Ama, Mayumi ^a   Fukuda, Takeshi ^a   Taki, Motohiko ^a   Naito, Satoru ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

3 Biphenylamino acid amides; 4 Aminophenoxyacetic acids; Cathepsin K inhibitors; Osteoporosis

Indexed keywords

4 AMINOPHENOXYACETIC ACID; ACETIC ACID DERIVATIVE; AMINOPHENOL DERIVATIVE; CATHEPSIN K INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG INHIBITION; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; LIPOPHILICITY;

CATHEPSINS; CYSTEINE PROTEINASE INHIBITORS; HUMANS; PHENOXYACETATES; RECOMBINANT PROTEINS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 32044434628     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.12.053     Document Type: Article

References (20)

1. The crystal structure of cathepsin K see: J.M. LaLonde, B. Zhao, C.A. Janson, K.J. D'Alessio, M.S. McQuency, M.J. Orsini, C.M. Debouck, and W.W. Smith Biochemistry 38 1999 862
2. J.-P. Falgueyret, R.M. Oballa, O. Okamoto, G. Wesolowski, Y. Aubin, R.M. Rydzewski, P. Prasit, D. Riendeau, S.B. Rodan, and M.D. Percival J. Med. Chem. 44 2001 94
3. R.M. Rydzewski, C. Bryant, R. Oballa, G. Wesolowski, S.B. Rodan, K.E. Bass, and D.H. Wong Bioorg. Med. Chem. 10 2002 3277
4. 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
5. R.W. Marquis, Y. Ru, J. Zeng, R.E. Trout, S.M. LoCastro, A.D. Gribble, J. Witherington, A.E. Fenwick, B. Garnier, T. Tomaszek, D. Tew, M.E. Hemling, C.J. Quinn, W.W. Smith, B. Zhao, M.S. McQueney, C.A. Janson, K. D'Alessio, and D.F. Veber J. Med. Chem. 44 2001 725
6. R.W. Marquis, Y. Ru, S.M. LoCastro, J. Zeng, D.S. Yamashita, H.-J. Oh, K.F. Erhard, L.D. Davis, T.A. Tomaszek, D. Tew, K. Salyers, J. Proksch, K. Ward, B. Smith, M. Levy, M.D. Cummings, R.C. Haltiwanger, G. Trescher, B. Wang, M.E. Hemling, C.J. Quinn, H.-Y. Cheng, F. Lin, W.W. Smith, C.A. Janson, B. Zhao, M.S. McQueney, K. D'Alessio, C.-P. Lee, A. Marzulli, R.A. Dodds, S. Blake, S.-M. Hwang, I.E. James, C.J. Gress, B.R. Bradley, M.W. Lark, M. Gowen, and D.F. Veber J. Med. Chem. 44 2001 1380
7. J.G. Catalano, D.N. Deaton, E.S. Furfine, A.M. Hassell, R.B. McFadyen, A.B. Miller, L.R. Miller, L.M. Shewchuk, D.H. Willard Jr., and L.L. Wright Bioorg. Med. Chem. Lett. 14 2004 275
8. F.X. Tavares, D.N. Deaton, A.B. Miller, L.R. Miller, L.L. Wright, and H.Q. Zhou J. Med. Chem. 47 2004 5049
9. F.X. Tavares, D.N. Deaton, L.R. Miller, and L.L. Wright J. Med. Chem. 47 2004 5057
10. D.G. Barrett, J.G. Catalano, D.N. Deaton, A.M. Hassell, S.T. Long, A.B. Miller, L.R. Miller, L.M. Shewchuk, K.J. Wells-Knecht, D.H. Willard Jr., and L.L. Wright Bioorg. Med. Chem. Lett. 14 2004 4897
11. E. Altmann, J. Renaud, J. Green, D. Farley, B. Cutting, and W. Jahnke J. Med. Chem. 45 2002 2352
12. E. Altmann, J. Green, and M. Tintelnot-Blomley Bioorg. Med. Chem. Lett. 13 2003 1997
13. T.-S. Kim, A.B. Hague, T.I. Lee, B. Lian, C.M. Tegley, X. Wang, T.L. Burgess, Y.-X. Qian, S. Ross, P. Tagari, C.-H. Lin, C. Mayeda, J. Dao, S. Jordan, C. Mohr, J. Cheetham, V. Viswanadhan, and A.S. Tasker Bioorg. Med. Chem. Lett. 14 2004 87
14. S.K. Thompson, S.M. Halbert, M.J. Bossard, T.A. Tomaszek, M.A. Levy, B. Zhao, W.W. Smith, S.S. Abdel-Meguid, C.A. Janson, K.J. D'Alessio, M.S. McQueney, B.Y. Amegadzie, C.R. Hanning, R.L. DesJarlais, J. Briand, S.K. Sarkar, M.J. Huddleston, C.F. Ijames, S.A. Carr, K.T. Garnes, A. Shu, J.R. Heys, J. Bradbeer, D. Zembryki, L. Lee-Rykaczewski, I.E. James, M.W. Lark, F.H. Drake, M. Gowen, J.G. Gleason, and D.F. Veber Proc. Natl. Acad. Sci. U.S.A. 94 1997 14249 For a docked structure of I into human cathepsin K see: Ref. 7b
15. D. Ma, Y. Zhang, J. Yao, S. Wu, and F. Tao J. Am. Chem. Soc. 120 1998 12459
16. O. Mitsunobu Synthesis 1981 1
17. R. Caputo, E. Cassano, L. Longobardo, and G. Palumbo Tetrahedron 51 1995 12337
18. T. Fukuyama, M. Cheung, and T. Kan Synlett 1999 1301
19. M.J. Bossard, T.A. Tomaszek, S.K. Thompson, B.Y. Amegadzie, C.R. Hanning, C. Jones, J.T. Kurdyla, D.E. McNulty, F.H. Drake, M. Gowen, and M.A. Levy J. Biol. Chem. 271 1996 12517
20. 50 value obtained in our assay was similar to the reported value (0.07 μM) see: Ref. 7.