A comparative SAR and computer modeling study of benzisothiazolone, mechanism-based inhibitors with porcine pancreatic and human leukocyte elastase

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 24, 1996, Pages 2941-2946

  Hlasta, Dennis J ^a,c   Court, John J ^a   Desai, Ranjit C ^a   Talomie, Timothy G ^a   Shen, Jian ^a   Dunlap, Richard P ^b   Franke, Catherine A ^b   Mura, Albert J ^b  

^a Sanofi Winthrop Inc   (United States)

^b EASTMAN KODAK COMPANY   (United States)

^c JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BENZISOTHIAZOLE DERIVATIVE; ELASTASE; LEUKOCYTE ELASTASE;

ANIMAL TISSUE; ARTICLE; COMPUTER SIMULATION; CONTROLLED STUDY; ENZYME BINDING; ENZYME INHIBITION; HUMAN; HUMAN TISSUE; LIPOPHILICITY; MOLECULAR DYNAMICS; NONHUMAN; PANCREAS; QUANTITATIVE STRUCTURE ACTIVITY RELATION; SWINE; X RAY CRYSTALLOGRAPHY;

EID: 0030591867     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(96)00553-7     Document Type: Article

References (21)

1. 3. Janoff, A. Amer. Rev. Respir. Dis. 1985, 132, 417. Gadek, J.E.; Fells, G.A.; Zimmerman, R.L.; Rennard, S.I.; Crystal, R.G. J. Clin. Invest. 1981, 68, 889.
2. 3. Janoff, A. Amer. Rev. Respir. Dis. 1985, 132, 417. Gadek, J.E.; Fells, G.A.; Zimmerman, R.L.; Rennard, S.I.; Crystal, R.G. J. Clin. Invest. 1981, 68, 889.
3. 4. Lee, C.T.; Fein, A.M.; Lippmann, M.; Holtzman, H.; Kimbel, P.; Weinbaum, G. N. Engl J. Med. 1981, 304, 192.
4. 5. Meyer, K.C.; Zimmerman, J. J. Lab. Clin. Med 1993, 121, 654. Jackson, A.H.; Hill, S.L.; Afford, S.C.; Stockley, R. A. J. Respir. Dis. 1984, 65, 114.
5. 5. Meyer, K.C.; Zimmerman, J. J. Lab. Clin. Med 1993, 121, 654. Jackson, A.H.; Hill, S.L.; Afford, S.C.; Stockley, R. A. J. Respir. Dis. 1984, 65, 114.
6. 6. Stockley, R. A. Clinics in Chest Medicine 1988, 9, 643.
7. 7. Hlasta, D. J.; Bell, M. R.; Boaz, N. W.; Court, J. J.; Desai, R. C.; Franke, C. A.; Mura, A. J;. Subramanyam, C.; Dunlap, R. P. Bioorg. Med. Chem. Lett. 1994, 4, 1801.
8. 8. Hlasta, D. J.; Bell, M. R.; Court, J. J.; Cundy, K. C.; Desai, R. C.; Ferguson, E. W.; Gordon, R. J.; Kumar, V.; Maycock, A. L.; Subramanyam, C.; Dunlap, R. P.; Eiff, S. L.; Franke, C. A.; Mura, A. J.; Rowlands, A. G. Bioorg. Med. Chem. Lett. 1995, 5, 331.
9. 9. Hlasta, D. J.; Subramanyam, C.; Bell, M. R.; Carabateas, P. M.; Court, J. J.; Desai, R. C.; Drozd, M. L.; Eickhoff, W. M.; Ferguson, E. W.; Gordon, R. J.; Johnson, J. A.; Kumar, V.; Maycock, A. L.; Mueller, K. R.; Pagani, E. D.; Robinson, D. T.; Saindane, M.; Silver, P. J.; Subramanian, S.; Dunlap, R. P.; Franke, C. A.; Mura, A. J.; Rowlands, A. J. Med. Chem. 1995, 38, 739.
10. 10. Zimmerman, M.; Morman, H.; Mulvey, D.; Jones, H.; Frankshun, R.; Ashe, B. M. J. Biol. Chem. 1980, 255, 9848. Ashe, B. M; Clark, R. L.; Jones, H.; Zimmerman, M. J. Biol. Chem. 1981, 256, 11603.
11. 10. Zimmerman, M.; Morman, H.; Mulvey, D.; Jones, H.; Frankshun, R.; Ashe, B. M. J. Biol. Chem. 1980, 255, 9848. Ashe, B. M; Clark, R. L.; Jones, H.; Zimmerman, M. J. Biol. Chem. 1981, 256, 11603.
12. 11. Daggett, V.; Schroder, S.; Kollman, P. J. Am. Chem. Soc. 1991, 113, 8926.
13. 12. Private communication by R. P. Dunlap of the Eastman Kodak Company. Reczek, J. A.; Welter, T. R. Eur. Pat. Appl. 56444 1982, CA 97(26): 227431t.
14. 13. Bode, W.; Meyer, Jr., E.; Powers, J. C. Biochemistry 1989, 28, 1951.
15. 14. The syntheses of the inhibitors discussed in this paper are described in ref 7 and in the following references. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, Jr., J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M.; Dunlap, R. P.; Franke, C. A.; Mura, A. J. J. Med Chem. 1994, 37, 2623. Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179. Subramanyam, C.; Bell, M. R. Bioorg. Med. Chem. Lett. 1991, 1, 733. Desai R. C.; Hlasta D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
16. 14. The syntheses of the inhibitors discussed in this paper are described in ref 7 and in the following references. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, Jr., J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M.; Dunlap, R. P.; Franke, C. A.; Mura, A. J. J. Med Chem. 1994, 37, 2623. Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179. Subramanyam, C.; Bell, M. R. Bioorg. Med. Chem. Lett. 1991, 1, 733. Desai R. C.; Hlasta D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
17. 14. The syntheses of the inhibitors discussed in this paper are described in ref 7 and in the following references. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, Jr., J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M.; Dunlap, R. P.; Franke, C. A.; Mura, A. J. J. Med Chem. 1994, 37, 2623. Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179. Subramanyam, C.; Bell, M. R. Bioorg. Med. Chem. Lett. 1991, 1, 733. Desai R. C.; Hlasta D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
18. 14. The syntheses of the inhibitors discussed in this paper are described in ref 7 and in the following references. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, Jr., J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M.; Dunlap, R. P.; Franke, C. A.; Mura, A. J. J. Med Chem. 1994, 37, 2623. Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179. Subramanyam, C.; Bell, M. R. Bioorg. Med. Chem. Lett. 1991, 1, 733. Desai R. C.; Hlasta D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
19. 14. The syntheses of the inhibitors discussed in this paper are described in ref 7 and in the following references. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, Jr., J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M.; Dunlap, R. P.; Franke, C. A.; Mura, A. J. J. Med Chem. 1994, 37, 2623. Hlasta, D. J.; Court, J. J.; Desai, R. C. Tetrahedron Lett. 1991, 32, 7179. Subramanyam, C.; Bell, M. R. Bioorg. Med. Chem. Lett. 1991, 1, 733. Desai R. C.; Hlasta D. J.; Monsour, G.; Saindane, M. T. J. Org. Chem. 1994, 59, 7161.
20. 15. Navia, M. A.; McKeever, B. M.; Springer, J. P.; Lin, T. -Y.; Williams, H. R.; Fluder, E. M.; Dorn, C. P.; Hoogsteen, K. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 7.
21. 16. Meyer, E.; Cole, G.; Radhakrishnan, R.; Epp, O. Acta Crystallogr., Sect. B 1988, 44, 26.