Potent, selective pyrone-based inhibitors of stromelysin-1

Journal of the American Chemical Society

Volumn 127, Issue 41, 2005, Pages 14148-14149

  Puerta, David T ^a   Mongan, John ^a   Tran, Ba L ^a   McCammon, J Andrew ^a   Cohen, Seth M ^a  

^a NONE

Author keywords

[No Author keywords available]

Indexed keywords

2 CARBOXY 3 BENZYLOXY 6 METHYLPYRAN 4(1H) ONE; GELATINASE A; HYDROXAMIC ACID DERIVATIVE; INTERSTITIAL COLLAGENASE; MATRIX METALLOPROTEINASE INHIBITOR; PYRONE DERIVATIVE; STROMELYSIN; STROMELYSIN INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION;

MATRIX METALLOPROTEINASE 3; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; PYRONES; STRUCTURE-ACTIVITY RELATIONSHIP; ZINC;

EID: 26844560948     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja054558o     Document Type: Article

References (19)

1. Skiles, J. W.; Gonnella, N. C.; Jeng, A. Y. Curr. Med. Chem. 2004, 11, 2911-2977.
2. Whittaker, M.; Floyd, C. D.; Brown, P.; Gearing, A. J. H. Chem. Rev. 1999, 99, 2735-2776.
3. Coussens, L. M.; Fingleton, B.; Matrisian, L. M. Science 2002, 295, 2387-2392.
4. Breuer, E.; Frant, J.; Reich, R. Expert Opin. Ther. Pat. 2005, 15, 253-269.
5. Hajduk, P. J. et al. J. Med. Chem. 2002, 45, 5628-5639.
6. Puerta, D. T.; Cohen, S. M. Curr. Top. Med. Chem. 2004, 4, 1551-1573.
7. Liu, Z. D.; Piyamongkol, S.; Liu, D. Y.; Khodr, H. H.; Lu, S. L.; Hider, R. C. Bioorg. Med. Chem. 2001, 9, 563-573.
8. Finnegan, M. M.; Rettig, S. J.; Orvig, C. J. Am. Chem. Soc. 1986, 108, 5033-5035.
9. Puerta, D. T.; Cohen, S. M. Inorg. Chem. 2003, 42, 3423-3430.
10. Chen, L.; Rydel, T. J.; Gu, F.; Dunaway, C. M.; Pikul, S.; McDow Dunham, K.; Barnett, B. L. J. Mol. Biol. 1999, 293, 545-557.
11. Puerta, D. T.; Schames, J. R.; Henchman, R. H.; McCammon, J. A.; Cohen, S. M. Angew. Chem., Int. Ed. 2003, 42, 3772-3774.
12. Böhm, H. J. J. Comput. Aided Mol. Des. 1994, 8, 623-632.
13. Hajduk, P. J. et al. J. Am. Chem. Soc. 1997, 119, 5818-5827.
14. Knight, C. G.; Willenbrock, F.; Murphy, G. FEBS Lett. 1992, 296, 263-266.
15. Castelhano, A. L.; Billedeau, R.; Dewdney, N.; Donnelly, S.; Home, S.; Kurz, L. J.; Liak, T. J.; Martin, R.; Uppington, R.; Yuan, Z.; Krantz, A. Bioorg. Med. Chem. Lett. 1995, 5, 1415-1420.
16. Puerta, D. T.; Lewis, J. A.; Cohen, S. M. J. Am. Chem. Soc. 2004, 126, 8388-8389.
17. Fray, M. J.; Dickinson, R. P.; Huggins, J. P.; Occleston, N. L. J. Med. Chem. 2003, 46, 3514-3525.
18. Johnson, L. L.; Pavlovsky, A. G.; Johnson, A. R.; Janowicz, J. A.; Man, C.-F.; Ortwine, D. F.; Purchase, C. F., II; White, A. D.; Hupe, D. J. J. Biol. Chem. 2000, 275, 11026-11033.
19. Corden, A. E. V.; Xu, J.; Raymond, K. N.; Durbin, P. Chem. Rev. 2003, 103, 4207-4282.