6-Acylamino-penam derivatives: Synthesis and inhibition of cathepsins B, L, K, and S

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 23, 2002, Pages 3417-3419

  Zhou, Nian E ^a   Kaleta, Jadwiga ^a   Purisima, Enrico ^b   Menard, Robert ^b   Micetich, Ronald G ^a   Singh, Rajeshwar ^a  

^a NAEJA Pharmaceutical Inc   (Canada)

^b NATIONAL RESEARCH COUNCIL CANADA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CATHEPSIN B; CATHEPSIN K; CATHEPSIN L; CATHEPSIN S; PENAM DERIVATIVE; 4 OXA 1 AZABICYCLO(3.2.0)HEPTAN 7 ONE; 4-OXA-1-AZABICYCLO(3.2.0)HEPTAN-7-ONE; AMINE; CATHEPSIN; CYSTEINE PROTEINASE INHIBITOR; LACTAM; SULFONE;

ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG OXIDATION; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; STEREOISOMERISM; CHEMISTRY; DRUG ANTAGONISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

AMINES; CATHEPSINS; CYSTEINE PROTEINASE INHIBITORS; INHIBITORY CONCENTRATION 50; LACTAMS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFONES;

EID: 0036888377     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00766-7     Document Type: Article

References (26)

1. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
2. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
3. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
4. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
5. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
6. Delaisse J.M., Ledent P., Vaes G. Biochem. J. 279:1991;167 Thomson S.K., Halbert S.M., Bossard M. J. Proc. Natl. Acad. Sci. U.S.A. 94:1997;14249 Maciewicz R.A., Van der Stapper J.W.J., Paraskewa C., Williams A.C., Hague A. Biochem. Soc. Trans. 19:1991;362 Esser R.E., Angelo R.A., Murphey M.B., Watts L.M., Thornburg L.P., Palmer J.T., Talhouk J.W., Smith R.E. Arthritis Rheum. 37:1994;236 Semenov A., Olson J.E., Rosental P.J. Antimicrobiol. Agents and Chemother. 42:1998;2254 Engel C., Doyle P., Hsieh I., McKerrow J.H. J. Exp. Med. 188:1998;725.
7. Chapman H.A., Riese R.J., Shi G.P. Annu. Rev. Physiol. 59:1997;63 Smith W.W., Abdel-Meguid S.S. Exp. Opin. Ther. Pat. 9:1999;683 Henkin J. Annu. Rep. Med. Chem. 28:1993;151 Michaud S., Gour B.J. Exp. Opin. Ther. Pat. 8:1998;645 Elliott E., Sloane B.F. Exp. Opin. Ther. Pat. 6:1996;12.
8. Chapman H.A., Riese R.J., Shi G.P. Annu. Rev. Physiol. 59:1997;63 Smith W.W., Abdel-Meguid S.S. Exp. Opin. Ther. Pat. 9:1999;683 Henkin J. Annu. Rep. Med. Chem. 28:1993;151 Michaud S., Gour B.J. Exp. Opin. Ther. Pat. 8:1998;645 Elliott E., Sloane B.F. Exp. Opin. Ther. Pat. 6:1996;12.
9. Chapman H.A., Riese R.J., Shi G.P. Annu. Rev. Physiol. 59:1997;63 Smith W.W., Abdel-Meguid S.S. Exp. Opin. Ther. Pat. 9:1999;683 Henkin J. Annu. Rep. Med. Chem. 28:1993;151 Michaud S., Gour B.J. Exp. Opin. Ther. Pat. 8:1998;645 Elliott E., Sloane B.F. Exp. Opin. Ther. Pat. 6:1996;12.
10. Chapman H.A., Riese R.J., Shi G.P. Annu. Rev. Physiol. 59:1997;63 Smith W.W., Abdel-Meguid S.S. Exp. Opin. Ther. Pat. 9:1999;683 Henkin J. Annu. Rep. Med. Chem. 28:1993;151 Michaud S., Gour B.J. Exp. Opin. Ther. Pat. 8:1998;645 Elliott E., Sloane B.F. Exp. Opin. Ther. Pat. 6:1996;12.
11. Chapman H.A., Riese R.J., Shi G.P. Annu. Rev. Physiol. 59:1997;63 Smith W.W., Abdel-Meguid S.S. Exp. Opin. Ther. Pat. 9:1999;683 Henkin J. Annu. Rep. Med. Chem. 28:1993;151 Michaud S., Gour B.J. Exp. Opin. Ther. Pat. 8:1998;645 Elliott E., Sloane B.F. Exp. Opin. Ther. Pat. 6:1996;12.
12. Reviews on cysteine proteases inhibitor: Otto H., Schirmeister T. Chem. Rev. 1997;133 Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2000;1 Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305 Marquis R.W. Annu. Rep. Med. Chem. 35:2000;309 Leung-Toung R., Li W., Tam T.F., Karimian K. Curr. Med. Chem. 9:2002;979.
13. Reviews on cysteine proteases inhibitor: Otto H., Schirmeister T. Chem. Rev. 1997;133 Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2000;1 Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305 Marquis R.W. Annu. Rep. Med. Chem. 35:2000;309 Leung-Toung R., Li W., Tam T.F., Karimian K. Curr. Med. Chem. 9:2002;979.
14. Reviews on cysteine proteases inhibitor: Otto H., Schirmeister T. Chem. Rev. 1997;133 Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2000;1 Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305 Marquis R.W. Annu. Rep. Med. Chem. 35:2000;309 Leung-Toung R., Li W., Tam T.F., Karimian K. Curr. Med. Chem. 9:2002;979.
15. Reviews on cysteine proteases inhibitor: Otto H., Schirmeister T. Chem. Rev. 1997;133 Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2000;1 Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305 Marquis R.W. Annu. Rep. Med. Chem. 35:2000;309 Leung-Toung R., Li W., Tam T.F., Karimian K. Curr. Med. Chem. 9:2002;979.
16. Reviews on cysteine proteases inhibitor: Otto H., Schirmeister T. Chem. Rev. 1997;133 Yamashita D.S., Dodds R.A. Curr. Pharm. Des. 6:2000;1 Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305 Marquis R.W. Annu. Rep. Med. Chem. 35:2000;309 Leung-Toung R., Li W., Tam T.F., Karimian K. Curr. Med. Chem. 9:2002;979.
17. Conroy J.L., Sanders T.C., Seto C.T. J. Am. Chem. Soc. 119:1997;4285 Conroy J.L., Abato P., Ghosh M., Austermuhle M.I., Kiefer M.R., Seto C.T. Tetrahedron Lett. 39:1998;8253.
18. Conroy J.L., Sanders T.C., Seto C.T. J. Am. Chem. Soc. 119:1997;4285 Conroy J.L., Abato P., Ghosh M., Austermuhle M.I., Kiefer M.R., Seto C.T. Tetrahedron Lett. 39:1998;8253.
19. Zhou, N. E.; Guo, D.; Kaleta, J.; Purisima, E.; Menard, R.; Micetich, R. G.; Singh, R. Bioorg. Med. Chem. Lett. 2002, 12, 3413.
20. Otani, T.; Oie, S.; Matsumoto, H.; Tempest, M.; Micetich, R. G.; Singh, R.; Yamashita, T. EP Patent 0 654 995 B1, 1993. Chem. Abstr. 1994, 121, 57497.
21. Newall, C. E., Hallam, P. D. In Comprehensive Medicinal Chemistry; Hansch, C., Sammes, P. J., Taylor, J. B., Eds.; Pergamon: Oxford 1990; p 605.
22. Zhou, N. E.; Guo, D.; Thomas, G.; Kaleta, J.; Micetich, R. G.; Singh, R. Bioorg. Med. Chem. Lett. Submitted for publication.
23. Micetich, R. G.; Singh, R.; Shaw, C. C. J. Org. Chem. 1986, 51, 1811. Micetich, R. G.; Singh, R.; Maiti, S. N. Heterocycles 1984, 22, 531.
24. Micetich, R. G.; Singh, R.; Shaw, C. C. J. Org. Chem. 1986, 51, 1811. Micetich, R. G.; Singh, R.; Maiti, S. N. Heterocycles 1984, 22, 531.
25. f and the ratio of isomers is determined based on C5 proton by NMR.
26. Barrett A.J., Kembhavi A.A., Brown M.A., Kirschke H., Knight G., Tamai M., Hanaka K. Biochem. J. 201:1982;189.