Design, Synthesis, and Evaluation of a Pyrrolinone-based Matrix Metalloprotease Inhibitor

Organic Letters

Volumn 2, Issue 24, 2000, Pages 3809-3812

  Smith III, Amos B ^a   Nittoli, Thomas ^a   Sprengeler, Paul A ^a   Duan, James J W ^b   Liu, Rui Qin ^b   Hirschmann, Ralph F ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ISOENZYME; METALLOPROTEINASE; PROTEINASE INHIBITOR; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DESIGN; SYNTHESIS;

ALDEHYDES; DRUG DESIGN; ISOENZYMES; METALLOENDOPEPTIDASES; MODELS, MOLECULAR; PROTEASE INHIBITORS; PYRROLES;

EID: 0034736381     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol000254p     Document Type: Article

References (40)

1. (a) Hirschmann, R. Proceedings of the 2nd Japan Symposium on Peptide Chemistry. Pept. Chem. 1992, 466.
2. (b) Hirschmann, R. Joseph Rudinger Award Lecture. Peptides 1996, 3.
3. (a) Smith, A. B., III; Hirschmann, R.; Pasternak, A.; Akaishi, R.; Guzman, M. C.; Jones, D. R.; Keenan, T. P.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Holloway, M. K.; Schleif, W. A. J. Med. Chem. 1994, 37, 215.
4. (b) Smith, A. B., III; Hirschmann, R.; Pasternak, A.; Guzman, M. C.; Yokoyama, A.; Sprengeler, P. A.; Darke, P. L.; Emini, E. A.; Schleif, W. A. J. Am. Chem. Soc. 1995, 117, 11113.
5. (c) Smith, A. B., III; Hirschmann, R.; Pasternak, A.; Yao, W.; Sprengeler, P. A.; Holloway, M. K.; Kuo, L. C.; Chen, Z.; Darke, P. L.; Schleif, W. A. J. Med. Chem. 1997, 40, 2440.
6. (d) Smith, A. B., III; Guzman, M. C.; Sprengeler, P. A.; Keenan, T. P.; Holcomb, R. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1994, 116, 9947.
7. (e) Smith, A. B., III; Holcomb, R. C.; Guzman, M. C.; Keenan, T. P.; Sprengeler, P. A.; Hirschmann, R. Tetrahedron Lett. 1993, 34, 63.
8. Smith, A. B., III; Keenan, T. P.; Holcomb, R. C.; Sprengeler, P. A.; Guzman, M. C.; Wood, J. L.; Carroll, P. J.; Hirschmann, R. J. Am. Chem. Soc. 1992, 114, 10672.
9. Hirschmann, R.; Smith, A. B., III; Sprengeler, P. A. New Perspectives in Drug Design; Dean, P. M., Jolles, G., Newton, C. G., Eds.; Academic Press: New York, 1995; p 1.
10. Smith, A. B., III; Akaishi, R.; Jones, D. R.; Keenan, T. P.; Guzman, M. C.; Holcomb, R. C.; Sprengeler, P. A.; Wood, J. L.; Hirschmann, R.; Holloway, M. K. Biopolymers 1995, 37, 29.
11. (a) Smith, A. B., III; Benowitz, A. B.; Guzman, M. C.; Sprengeler, P. A.; Hirschmann, R.; Schweiger, E. J.; Bolin, D. R.; Nagy, Z.; Campbell, R. M.; Cox, D. C.; Olson, G. L. J. Am. Chem. Soc. 1998, 120, 12704.
12. (b) Smith, A. B. III; Benowitz, A. B.; Sprengeler, P. A.; Barbosa, J.; Guzman, M. C.; Hirschmann, R.; Schweiger, E. J.; Bolin, D. R.; Nagy, Z.; Campbell, R. M.; Cox, D. C.; Olson, G. L. J. Am. Chem. Soc. 1999, 121, 9286.
13. Smith, A. B., III; Wang, W.; Sprengeler, P. A.; Hirschmann, R. J. Am. Chem. Soc., submitted for publication.
14. (a) Birkedal-Hansen, H. J. Oral Pathol. 1988, 17, 445.
15. (b) Birkedal-Hansen, H. Curr. Opin. Cell Biol. 1995, 7, 728.
16. (c) Emonard, H.; Grimaud, J. A. Cell. Mol. Biol. 1990, 36, 131.
17. (d) Murphy, G.; Docherty, A. J. P. Am. J. Respir. Cell Mol. Biol. 1992, 7, 120.
18. (e) Baramova, E.; Foidart, J. Cell Biol. Int. 1995, 19, 239.
19. (f) Borkakoti, N. Prog. Biophys. Mol. Biol. 1998, 70, 73.
20. (g) Johnson, L. L., Dyer, R., Hupe, D. J. Curr. Opin. Chem. Biol. 1998, 2, 466.
21. (h) Shapiro, S. D.; Senior, R. M. Am. J. Respir. Cell Mol. Biol. 1999, 20, 1100.
22. (a) Chandler, S.; Miller, K. M.; Clements, J. M.; Lury, J.; Corkill, D.; Anthony, D. C. C.; Adams, S. E.; Gearing, A. J. H. J. Neuroimmunol. 1997, 72, 155.
23. (b) Toi, M.; Ishigaki, S.; Tominaga, T. Breast Cancer Res. Treat. 1998, 52, 113.
24. (c) Michaelides, M. R.; Curtin, M. L. Curr. Pharm. Des. 1999, 5, 787.
25. (d) Lukes, A.; Mun-Bryce, S.; Lukes, M.; Rosenberg, G. A. Mol. Neurobiol. 1999, 19, 267.
26. (e) Kieseier, B. C.; Seifert, T.; Giovannoni, G.; Hartung, H. Neurology 1999, 53, 20.
27. (f) Curran, S.; Murray, G. I. J. Pathol. 1999, 189, 300.
28. (g) Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735.
29. Zask, A.; Levin, J. I.; Killar, L. M., Skotnicki, J. S. Curr. Pharm. Des. 1996, 2, 624.
30. Johnson, W. H.; Roberts, N. A.; Borkakoti, N. J. Enzyme Inhib. 1987, 2, 1.
31. Borkakoti, N.; Winkler, F. K.; Williams, D. H.; D'Arcy, A.; Broadhurst, M. J.; Brown, P. A.; Johnson, W. H.; Murray, E. J. Struct. Biol. 1994, 1, 106.
32. MacroModel, ver 5.0; Still, W. C.; Mohamadi, F.; Richards, N. G. J.; Guida, W. C.; Lipton, M., Liskamp, R.; Chang, G.; Hendrickson, T.; Degunst, F.; Hasel, W. Department of Chemistry, Columbia University: New York, 10027.
33. Penning; T. D.; Djuric, S. W.; Haack, R. A.; Kalish, V. J.; Miyashiro, J. M.; Rowell, B. W.; Yu, S. S. Synth. Comm. 1990, 20, 307.
34. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
35. (b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
36. (c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
37. Nikam, S. S.; Kornberg, B. E., Johnson, D. R.; Doherty, A. M. Tetrahedron Lett. 1995, 36, 197-200.
38. Castelhano, A. L.; Billedeau, R.; Dewdney, N.; Donnelly, S.; Horne, S.; Kurz, L. J.; Liak, T. J.; Martin, R.; Uppington, R.; Yuan, Z.; Krantz, A. Bioorg. Med. Chem. Lett. 1995, 5, 1415.
39. We speculate that although all of the anticipated hydrogen bonds in the modeled active-site of MMP-1 with (-)-1 were within 3 Å in length, optimal geometries were not achieved, thereby reducing their strength. Optimal hydrogen bonding occurs when the donor, hydrogen, and acceptor atoms are colinear. Streyer, L. Biochemistry, 3rd ed.; W. H. Freeman: New York, 1988; p 8.
40. Smith, A. B., III; Liu, H.; Okumura, H.; Favor, D. A.; Hirschmann, R. F. Org. Lett. 2000, 2, 2041.