Structure-based design and synthesis of a series of hydroxamic acids with a quaternary-hydroxy group in P1 as inhibitors of matrix metalloproteinases

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 7, 1998, Pages 837-842

  Jacobson, Irina C ^a   Reddy, Prabhakar G ^a   Wasserman, Zelda R ^a   Hardman, Karl D ^a   Covington, Maryanne B ^a   Arner, Elizabeth C ^a   Copeland, Robert A ^a   Decicco, Carl P ^a   Magolda, Ronald L ^a  

^a DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXAMIC ACID DERIVATIVE; MATRIX METALLOPROTEINASE; METALLOPROTEINASE INHIBITOR;

ARTICLE; DRUG ACTIVITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

CATALYTIC DOMAIN; COLLAGENASES; COMPUTER SIMULATION; DRUG DESIGN; ENZYME PRECURSORS; HYDROGEN BONDING; HYDROXAMIC ACIDS; INDICATORS AND REAGENTS; MATRIX METALLOPROTEINASE 1; MATRIX METALLOPROTEINASE 3; METALLOENDOPEPTIDASES; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; PROTEIN CONFORMATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032492646     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00125-5     Document Type: Article

References (20)

1. 1. (a) Johnson, W. H.; Roberts, N. A.; Borkakoki, N. J. Enzyme Inhib. 1987, 2, 1.
2. (b) Henderson, B.; Docherty, A. J. P.; Beeley, N. R. A. Drugs Future 1990, 15, 495.
3. (c) Emonard, H.; Grimaud, H Cell. Mol. Biol. 1990, 36, 131.
4. (d) Woessner, J. F. FASEB J. 1991, 5, 2145.
5. (e) Murphy, G. J. P.; Murphy, G; Reynolds, J. J. FEBS Lett. 1991, 289, 4.
6. (f) Cawston, T. E. British Medical Bulletin 1995, 51, 385.
7. 2. Nagase, H.; Barrett, A. J.;Woessner, J. F. In Matrix Metalloproteinases and Inhibitors; Birkedal - Hansen, H.; Werb, Z.; Welgus, H. G.; Van Wart, H. E., Eds.; Gustav Fischer Verlag: New York, 1992; pp 421-424.
8. 3. (a) Dean, D. D.; Martel - Pelletier, J.; Pelletier, J.-P.; Howell, D. S.; Woessner, J. F. Clin. Invest. 1989, 84, 678.
9. (b) Hasty, K. A.; Reife, R. A.; Kang, A. H.; Stuart, J. M. Arth. Rheum, 1990, 33, 388.
10. (c) Walakovits, L. A.; Bhardwaj, N.; Gallick, G. S.; Lark, M. W. Arth. Rheum. 1992, 35, 35.
11. 4. (a) Schwarte, M. A.; Van Wart, H. E. In Progress in Medicinal Chemistry; Ellis, G. P.; Luscombe, D. K.; Eds.; Elsevier Science: The Netherlands 1992; Vol. 29.
12. (b) Porter, J. R.; Millican, T. A.; Morphy, J. R. Exp. Opin. Ther. Patents 1995, 5, 1287.
13. (c) Scrip 2084, 23 (1995).
14. (d) Beckett, R. P.; Davidson, A. H.; Drummond, A. H.; Huxley, P.; Whittaker, M. Drug Discovery Today 1996, 1, 16.
15. (e) Beckett, R. P. Exp. Opin. Ther. Patents 1996, 6, 1305.
16. (f) Hagmann, W. K.; Lark, M. W.; Becker, J. W. In Annual Reports in Medicinal Chemistry; Bristol, J. A., Ed.; Academic: New York, 1996; Vol. 31, pp 231-240.
17. 5. Dhanaraj, V.; Ye, Q.-Z.; Johnson, L. L.; Hupe, D. J.; Ortwine, D. F.; Dunbar Jr., J. B.; Rubin, J. R.; Pavlovsky, A.; Humblet, C.; Blundell, T. L. Structure 1996, 4, 375.
18. 1H NMR and mass spectroscopy.
19. 7. Jacobson, I. C.; Reddy, G. P. Tetrahedron Lett. 1996, 37, 8263.
20. 8. Hardman, K. D.; Jacobson, I. C.; Decicco, C. P. Protein Society European Symposium; Cambridge, UK, 1997.