Design, synthesis, and in vitro inhibitory activity toward human leukocyte elastase, cathepsin G, and proteinase 3 of saccharin-derived sulfones and congeners

Bioorganic and Medicinal Chemistry

Volumn 4, Issue 9, 1996, Pages 1393-1400

  Groutas, William C ^a   Epp, Jeffrey B ^a   Venkataraman, Radhika ^a   Kuang, Rongze ^a   Truong, Tien My ^a   McClenahan, Jerry J ^a   Prakash, Om ^b  

^a WICHITA STATE UNIVERSITY   (United States)

^b KANSAS STATE UNIVERSITY   (United States)

Author keywords

Cathepsin G; Elastase; Inhibitors; Proteinase 3; Saccharin derivatives; Serine proteases

Indexed keywords

CATHEPSIN G; ELASTASE; PROTEINASE; SACCHARIN DERIVATIVE;

ARTICLE; CONTROLLED STUDY; DRUG DESIGN; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN TISSUE; IN VITRO STUDY; LEUKOCYTE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PKA; STRUCTURE ACTIVITY RELATION;

EID: 0029740848     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/0968-0896(96)00133-2     Document Type: Article

References (36)

1. Bernstein, P. R.; Edwards, P. D.; Williams, J. C. Prog. Med. Chem. 1994, 31, 59.
2. Crystal, R. G. J. Clin. Invest. 1990, 85, 1343.
3. Wiedow, O.; Wiese, F.; Streit, V.; Kalm, C.; Christophers, E. J. Invest. Dermatol. 1992, 99, 306.
4. Meyer, K. C.; Lewandoski, J. R.; Zimmerman, J. J.; Nunley, D.; Calhoun, W. J.; Dopico, G. A. Am. Rev. Resp. Dis. 1991, 144, 580.
5. Edwards, S. W. Biochemistry and Physiology of the Neutrophil; Cambridge University: New York, 1994.
6. Baggiolini, M.; Clarke-Lewis, I. FEBS Lett. 1993, 307, 97.
7. McElvaney, N. G.; Nakamura, H.; Birrer, P.; Hebert, C. A.; Wong, W. L.; Alphonso, M.; Baker, J. B.; Catalano, M. A.; Crystal, R. G. J. Clin. Invest. 1992, 90, 1296.
8. Constan, M. W.; Walenga, R. W.; Hilliard, K. A.; Hilliard, J. B. Am. Rev. Resp. Dis. 1993, 148, 896.
9. Kao, R. C.; Wehner, N. G.; Skubitz, K. M.; Gray, B. H.; Hoidal, J. R. J. Clin. Invest. 1988, 82, 1963.
10. Janusz, M. J.; Doherty, N. S. J. Immunol. 1991, 146, 3922.
11. Janoff, A. Am. Rev. Resp. Dis. 1985, 133, 149.
12. Birrer, P.; McElvaney, N. G.; Rudeberg, A.; Sommer, C. W.; Liechti-Gallati, S.; Kraemer, R.; Hubbard, R.; Crystal, R. G. Am. J. Resp. Crit. Care Med. 1994, 150, 207.
13. Edwards, P. D.; Bernstein, P. R. Med. Res. Rev. 1994, 14, 127.
14. Weinbaum, G.; Groutas, G. C. In Focus on Pulmonary Pharmacology and Toxicology; Hollinger, M. A., Ed.; CRC: Boca Raton, 1991.
15. Ono, N.; Miyake, H.; Saito, T.; Kar, A. Synthesis 1980, 952.
16. Tuleen, D. L.; Stephens, T. B. J. Org. Chem. 1969, 34, 31.
17. Groutas, W. C.; Houser-Archield, N.; Chong, L. S.; Venkataraman, R.; Epp, J. B.; Huang, H.; McClenahan, J. J. J. Med. Chem. 1993, 36, 3178.
18. Groutas, W. C.; Brubaker, M. J.; Stanga, M. A.; Castrisos, J. C.; Crowley, J. P.; Schatz, E. J. J. Med. Chem 1989, 32, 1607.
19. (a) Groutas, W. C.; Venkataraman, R.; Brubaker, M. J.; Stanga, M. A. Biochemistry 1991, 30, 4132
20. (b) Groutas, W. C.; Brubaker, M. J.; Venkataraman, R.; Epp, J. B.; Stanga, M. A.; McClenahan, J. J. Arch. Biochem. Biophys. 1992, 294, 144.
21. Hill, J. H. M. J. Org. Chem. 1965, 30, 620.
22. Zinnes, H.; Comes, R. A.; Shavel, J. J. Org. Chem. 1964, 29, 2068.
23. Gabriel, S.; Colman, J. Chem. Ber. 1900, 33, 980.
24. (a) Groutas, W. C.; Chong, L. S.; Venkataraman, R.; Epp, J. B.; Kuang, R.; Brubaker, M. J.; Houser-Archield, N.; Huang, H.; McClenahan, J. J. Biochem. Biophys. Res. Comm. 1993, 194, 1491
25. (b) Groutas, W. C.; Brubaker, M. J.; Venkataraman, R.; Epp, J. B.; Houser-Archield, N.; Chong, L. S.; McClenahan, J. J. Bioorg. Med. Chem. Lett. 1992, 2, 175;
26. For an exception, see Groutas, W. C.; Chong, L. S.; Venkataraman, R.; Huang, H.; Epp, J. B.; Kuang, R. Bioorg. Med. Chem. Lett. 1993, 3, 2745.
27. Groutas, W. C.; Houser-Archield, N.; Chong, L. S.; Venkataraman, R.; Epp, J. B.; Huang, H.; McClenahan, J. J. J. Med. Chem. 1993, 36, 3178.
28. Groutas, W. C.; Huang, H.; Venkataraman, R.; Houser-Archield, N.; Epp, J. B. Bioorg. Med. Chem. 1993, 1, 273.
29. (a) Dunlap, R. P.; Boaz, N. W.; Mura, A. J.; Hlasta, D. J. Chem. Abstr. 1991, 114, 228897f
30. (b) Hlasta, D. J.; Bell, M.; Boaz, N.; Court, J.; Desai, R.; Eiff, S.; Franke, C.; Mura, A.; Subramanyam, C.; Dunlap, R. 202nd ACS National Meeting, 28 August, 1991, New York.
31. 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.
32. Subramanyam, C.; Bell, M. R.; Carabateas, P.; Court, J. J.; Dority, J. A.; Ferguson, E.; Gordon, R.; Hlasta, D. J.; Kumar, V.; Saindane, M. J. Med. Chem. 1994, 37, 2623, and ref cited therein.
33. Oae, S. Organic Sulfur Chemistry: Structure and Mechanism; CRC: Boca Raton, 1991.
34. Kam, C.-H.; Fujikawa, K.; Powers, J. C. Biochemistry 1988, 27, 2547.
35. The high expense of HLE necessitated the use of α-chymotrypsin.
36. Nash, T. Biochem. J 1953, 55, 416.