Thiol inhibitors of endothelin-converting enzyme

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 19, 1996, Pages 2317-2322

  Deprez, Pierre ^a   Guillaume, Jacques ^a   Dumas, Jacques ^a   Vevert, Jean Paul ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIN CONVERTING ENZYME; ENZYME INHIBITOR; PHOSPHORAMIDON; THIOL DERIVATIVE;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME INHIBITION; IN VITRO STUDY; NONHUMAN; RAT; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030575610     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00420-9     Document Type: Article

References (29)

1. (1) Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayishi, Y.; Mitsui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. Nature, 1988, 332, 411.
2. (2) Rubanyi, G. M.; Polokoff, M. A. Pharmacol. Rev. 1994, 46, 325.
3. (3) a) Opgenorth, T. J.; Wu-Wong, J. R.; Shiosaki, K. FASEB J. 1992, 6, 2653.
4. b) Turner, A. J. Biochem Soc. Trans., 1993, 21, 697.
5. c) Turner, A. J.; Murphy, L. J. Biochem. Pharmacol., 1996, 51, 91.
6. 4) a) Waxman, L.; Doshi, K.P.; Gaul, S.L.; Wang, S.; Bednar, R.A.; Stern, A.M.; Arch. Biochem. Biophys. 1994, 308, 240.
7. b) Takahashi, M.; Matsushita, Y.; Iijima, Y.; Tanzawa, K., J. Biol. Chem., 1993, 268, 21394.
8. c) Ohnaka, K.; Takayanagi; Nishikawa; M.; Haji, M.; Newata, H. J. Biol. Chem., 1993, 26759.
9. (5) a) Shimada, K.; Takahashi, M.; and Tanzawa, K. J. Biol. Chem. 1994, 269, 18275.
10. b) Xu, D.; Emoto, N.; Giaid, A.; Slaughter, C.; Kaw, S.; de Wit, D.; Yanagisawa, M. Cell, 1994, 78, 473.
11. (c) Ikura, T.; Sawamura, T.; Shiraki, T.; Hosokawa, H.; Kido, T.; Hoshikawa, H.; Shimada, K.; Tanzawa, K.; Kobayashi, S.; Miwa, S.; and Masaki, T. Biochem. Biophys. Res. Commun. 1994, 203, 1417.
12. d) Schmidt, M.; Kröger, B.; Jacob, E.; Seulberger, H.; Subkowski, T.; Otter, R.; Meyer, T.; Schmalzing, G.; and Hillen, H. FEBS Lett. 1994, 356, 238.
13. e) Emoto, N.; Yanagisawa M. J. Biol. Chem. 1995, 270, 15262.
14. f) Shimada K., Takahashi M.; Ikeda M.; Tanzawa, K. FEBS Lett., 1995, 371, 140.
15. (6) Warner, T. D.; Battistini, D.; Doherty, A. M.; Corder, R. Biochem. Pharmacol. 1994, 48, 625.
16. (7) a) Bertenshaw, S. R.; Rogers, R. S.; Stern, M. K.; Norman, B. H. J. Med. Chem., 1993, 36, 173.
17. b) Fukami, T.; Hayama, T.; Amano, Y.; Nakamura, Y.; Arai, Y.; Matsuyama, K.; Yano, M.; Ishikawa, K.; Bioorg. Med. Chem. Lett., 1994, 4, 1257.
18. c) Bihovsky, R.; Levinson, B. L.; Loewi, R. C.; Erhardt, P. W.; Polokoff, M. A. J. Med. Chem., 1995, 38, 2119.
19. d) Bertenshaw,; Talley, J. J.;. Rogers, R.S.; Carter, J. S.; Moore, W. M.; Branson, L. M.; Koboldt, C. M. Bioorg. Med. Chem. Lett., 1993, 3, 1953.
20. e) de Lombaert, S.; Ghaia, R. D.; Jeng, A.Y.; Trapani, A. J.; Webb, R. L. Biochem. Biophys. Res. Comm., 1994, 204, 407.
21. f) Tsurumi, Y.; Ueda, H.; Hayashi, K.; Takase, S.; Nishikawa, M.; Kiyoto, S.; Okuhara, M., J. Antibiotics, 1995, 45, 1066,
22. g) Tsurumi, Y.; Ohhata, N.; Iwamoto, T.; Shigematsu, N.; Sakamoto, K.; Nishikawa, M.; Kiyoto, S.; Okuhara, M. J. Antibiotics, 1994, 47, 619.
23. h) Kukkola, P. J.; Bilci, N. A.; Kozak, W. X.; Savage, P.; Jeng, A. Y. Bioorg. Med. Chem. Lett., 1996, 6, 619.
24. (8) Miyaura, N.; Yanagi, T.; Suzuki, A. Synt. Comm. 1981, 11 (7), 513-519.
25. (9) Giros, B.; Gros, C.; Schwartz, J.-C.; Danvy, D.; Plaquevent, J.-C.; Duhamel, L.; Duhamel, P.; Vlaiculescu, A.; Costentin, J.; Lecomte, J.-M. J. Pharmacol. Exp. Therapeutics 1987, 243, 666.
26. 8 Pd catalysed coupling reaction with a range of commercially available boronic acids, as.described by Shieh, W.-C.; Carlson, J. A. J. Org. Chem. 1992, 57, 379.
27. (11) Strijtveen, B.; Kellogg, R. M. J. Org. Chem. 1986, 51, 3664.
28. (12) Dumas, J.; Roques, B.-P. Anal. Biochem., to be submitted.
29. (13) Bhagwat, S.S.; Fink, C.A.; Gude, C.; Chan, K.; Qiao, Y.; Sakane, Y.; Berry, C.; Ghai, R.D. Bioorg. Med. Chem. Lett., 1995, 5, 735.