Rational design of potent and selective NH-linked aryl/heteroaryl cathepsin K inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 16, 2004, Pages 4291-4295

  Robichaud, Joël ^a   Bayly, Christopher ^a   Oballa, Renata ^a   Prasit, Peppi ^a   Mellon, Christophe ^a   Falgueyret, Jean Pierre ^a   David Percival, M ^a   Wesolowski, Gregg ^b   Rodan, Sevgi B ^b  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Biaryl piperazine; Bone resorption; Cathepsin K inhibitors; Modelling

Indexed keywords

ANILINE; CATHEPSIN B; CATHEPSIN K; CATHEPSIN L; CATHEPSIN S; CYSTEINE PROTEINASE INHIBITOR; THIOPHENE;

ARTICLE; DRUG DESIGN; DRUG POTENCY; HYDROGEN BOND; HYPOTHESIS; MODEL; OSTEOLYSIS;

BINDING SITES; CATHEPSINS; CYSTEINE PROTEINASE INHIBITORS; HYDROGEN BONDING; MODELS, MOLECULAR;

FELIS CATUS;

EID: 3142742330     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.05.087     Document Type: Article

References (13)

1. Motyckova G., Fisher D.E. Curr. Mol. Med. 2:2002;407
2. For recent reviews on this subject see: Stroup G.B., Lark M.W., Veber D.F., Bhattacharyya A., Blake S., Dare L.C., Erhard K.F., Hoffman S.J., James I.E., Marquis R.W., Ru Y., Vasko-Moser J.A., Smith B.R., Tomaszek T., Gowen M. J. Bone Miner. Res. 16:2001;1739
3. Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2001;1
4. Robichaud J., Oballa R., Prasit P., Falgueyret J.-P., Percival M.D., Wesolowski G., Rodan S.B., Kimmel D., Johnson C., Bryant C., Venkatraman S., Setti E., Mendoca R., Palmer J.T. J. Med. Chem. 46:2003;3709
5. Chen C.-Y., Dagneau P., Grabowski E.J.J., Oballa R., O'Shea P., Prasit P., Robichaud J., Tillyer R., Wang X. J. Org. Chem. 68:2003;2633
6. Suzue S., Irikura T. Chem. Pharm. Bull. 16:1968;1417
7. DesJarlais R.L., Yamashita D.S., Oh H.-J., Uzinskas I.N., Erhard K.F., Allen A.C., Haltiwanger R.C., Zhao B., Smith W.W., Abdel-Meguid S.A., D'Alessio K., Janson C.A., McQueney M.S., Tomaszek T.A., Levy M.A., Veber D.F. J. Am. Chem. Soc. 120:1998;9114
8. For a similar approach, see: Greenspan P.D., Clark K.L., Cowen S.D., McQuire L.W., Tommasi R.A., Farley D.L., Quadros E., Coppa D.E., Du Z., Fang Z., Zhou H., Doughty J., Toscano K.T., Wigg A.M., Zhou S. Bioorg. Med. Chem. Lett. 13:2003;4121
9. McGrath M.E., Klaus J.L., Barnes M.G., Bromme D. Nat. Struct. Biol. 4:1997;105. PDB entry 1MEM
10. Case, D. A.; Pearlman, D. A.; Caldwell, J. W.; Cheatham III, T. E.; Ross, W. S.; Simmerling, C. L.; Darden, T. A.; Merz, K. M.; Stanton, R. V.; Cheng, A. L.; Vincent, J. J.; Crowley, M.; Tsui, V.; Radmer, R. J.; Duan, Y.; Pitera, J.; Massova, I.; Seibel, G. L.; Singh, U. C.; Weiner, P. K.; Kollman, P. A. (1999), AMBER 6, University of California, San Francisco
11. Falgueret J.P., Oballa R.M., Okamoto O., Wesolowski G., Aubin Y., Rydzewski R.M., Prasit P., Riendeau D., Rodan S.B., Percival M.D. J. Med. Chem. 44:2001;94
12. Ma D., Zhang Y., Yao J., Wu S., Tao F. J. Am. Chem. Soc. 120:1998;12459
13. Saito K., Harada K. Bull. Chem. Soc. Jpn. 62:1989;2562