Human chymase inhibitors based on the 1,2,5-thiadiazolidin-3-one 1,1 dioxide scaffold

Bioorganic and Medicinal Chemistry Letters

Volumn 9, Issue 15, 1999, Pages 2199-2204

  Groutas, William C ^a   Schechter, Norman M ^b   He, Shu ^a   Yu, Hongyi ^a   Huang, Peng ^a   Tu, Juan ^a  

^a WICHITA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHYMASE; ENZYME INHIBITOR; SERINE PROTEINASE INHIBITOR;

ARTICLE; BLOOD PRESSURE REGULATION; DRUG DESIGN; DRUG EFFICACY; DRUG MECHANISM; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN TISSUE;

CHYMASES; CYCLIC S-OXIDES; ENZYME INHIBITORS; HUMANS; SERINE ENDOPEPTIDASES; SKIN; STRUCTURE-ACTIVITY RELATIONSHIP; THIADIAZOLES;

EID: 0033517091     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(99)00377-7     Document Type: Article

References (27)

1. (a) Caughey, G. H. J. Respir. Crit. Care Med. 1994, 150, S138.
2. (b) Wang, Z.; Walter, M.; Selwood, T.; Rubin, H.; Schechter, N. M. Biol. Chem. 1998, 379, 167.
3. 1 is the primary specificity site.
4. Schechter, N. M.; Jordan, L. M.; James, M.; Cooperman, B. S.; Wang, Z-M.; Rubin, H. J. Biol. Chem. 1993, 268, 23626.
5. (a) Sanker, S.; Chandresakharan, U. M.; Milk, D.; Glynias, M. J.; Karnik, S. S.; Husain, A. J. Biol. Chem. 1997, 272, 2963.
6. (b) Kinoshita, A.; Urata, H.; Bumpus, F. M.; Husain, A. ibid., 1991, 266, 19192.
7. (a) Wolny, A.; Clozel, J-P.; Rein, J.; Mory, P.; Vogt, P.; Turino, M.; Kiowski, W.; Fischli, W. Circulation Res. 1991, 80, 219.
8. (b) Liao, Y.; Husain, A. Can. J. Cardiol. 1995, 11 (Suppl F), 13F.
9. Saarinen, J.; Kalkkinnen, N.; Welgus, H. G.; Kovanen, P. T. J. Biol. Chem. 1994, 269, 18134.
10. Mizutani, H.; Schechter, N. M.; Lazarus, G. S.; Black, R. A.; Kupper, T. S. J. Exp. Med 1991, 174, 821
11. Powers, J. C.; Tanaka, T.; Harper, J. W.; Minematsu, Y.; Barker, L.; Danforth, L.; Crumley, K. V.; Fraki, J. E.; Schechter, N. M.; Lazarus, G. G.; Nakajima, K.; Nakashino, K.; Neurath, H.; Woodbury, R. G. Biochemistry 1985, 24, 2048.
12. Kato, Y.; Kido, H.; Fukusen, N.; Katunuma, N. J. Biochem. 1988, 103, 820.
13. Bastos, M.; Meiji, N. J.; Abeles, R. H. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6738.
14. (a) Eda, M.; Ashimori, A.; Akahoshi, F.; Yoshimura, T.; Inoue, Y.; Fukaya, C.; Nakajima, M.; Fukuyama, H.; Imada, T.; Nakamura, N. Bioorg. Med. Chem. Lett. 1998, 8, 913.
15. (b) Eda, M.; Ashimori, A.; Akahoshi, F.; Yoshimura, I.; Fukaya, C.; Nakajima, M.; Fukuyama, H.; Imada, T.; Nakamura, N. ibid. 1998, 8, 919.
16. Niwata, S.; Fukami, H.; Sumida, M.; Ito, A.; Katutani, S.; Saitoh, M.; Suzuki, K.; Imoto, M.; Shibata, H; Imajo, S.; Kiso, Y.; Tanaka, T.; Nakazato, H.; Ishihara, T.; Takai, S.; Yamamoto, D.; Shiota, N.; Miyazaki, M.; Okunishi, H.; Kinoshita, A.; Urata, H.; Arakawa, K. J. Med. Chem. 1997, 40, 2156.
17. Fukami, H.; Okunishi, H.; Miyazaki, M. Curr. Pharm. Des. 1998, 4, 439.
18. (a) Groutas, W. C.; Kuang, R.; Venkataraman, R.; Epp, J. B.; Ruan, S.; Prakash, O. Biochemistry 1997, 36, 4739.
19. (b) Groutas, W. C.; Kuang, R.; Ruan, S.; Epp, J. B.; Venkataraman, R.; Truong, T. Bioorg. Med. Chem. 1998, 6, 661.
20. (c) Kuang, R.; Venkataraman, R.; Ruan, S.; Groutas, W. C. Bioorg. Med. Chem. Lett. 1998, 8, 539.
21. (d) Kuang, R.; Epp, J. B.; Ruan, S.; Yu, H.; Huang, P.; He, S.; Tu, J.; Schechter, N. M.; Turbov, J.; Froelich, C. J.; Groutas, W. C. J. Am. Chem. Soc., in press.
22. Webb, K. S. Tetrahedron Lett. 1994, 35, 3457.
23. Broughman, P.; Cooper, M. S.; Cummerson, D. A.; Heaney, H.; Thomson, N. Synthesis 1987, 1015.
24. All compounds were characterized by full spectroscopic data.
25. Morrison, J. F.; Walsh, C. T. Adv. Enzymol. 1988, 61, 201.
26. McGrath, M. E.; Mirzadegan, T.; Schmidt, B. F. Biochemistry 1997, 36, 14318.
27. Hof, P.; Mayr, I.; Huber, R.; Korzus, E.; Potempa, J.; Travis, J.; Powers, J. C.; Bode, W. EMBO J. 1996, 15, 5481.