Halogen substitution at the isoxazole ring enhances the activity of N-(isoxazolyl)sulfonamide endothelin antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 20, 1996, Pages 2393-2398

  Chan, Ming Fai ^c,d   Raju, B ^c   Kois, Adam ^c   Castillo, Rosario S ^c   Verner, Erik J ^c   Wu, Chengde ^c   Hwang, Emily ^a   Okun, Ilya ^a   Stavros, Fiona ^a   Balaji, V N ^b  

^a Depts of Med Chem Biochem P   (United States)

^b Dept of Computational Chemistry ^*  (United States)

^c ImmunoPharmaceutics Inc   (United States)

^d Palomar Research Inc   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIN A RECEPTOR; ENDOTHELIN B RECEPTOR; ENDOTHELIN RECEPTOR ANTAGONIST; SULFONAMIDE;

ANIMAL TISSUE; AORTA; ARTICLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; HALOGENATION; HUMAN; NONHUMAN; NORMAL HUMAN; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SMOOTH MUSCLE CONTRACTION;

ANIMALIA;

EID: 0030598177     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00441-6     Document Type: Article

References (20)

1. 1. Presented in part at the 209th ACS National Meeting, Anaheim, CA, April 2-6, 1995, Abstract MEDI 167.
2. 2. Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitsui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. Nature (London) 1988, 332, 411.
3. 3. (a) Inoue, A; Yanagisawa, M.; Kimura, S.; Miyauichi, T.; Goto, K.; Masaki, T. Proc. Natl. Acad. Sci. U.S.A., 1989, 86, 2863;
4. (b) Shinmi, O.; Kimura, S.; Sawamura, T.; Sugita, Y.; Yoshizawa, T. Biochem. Biophys. Res. Commun. 1989, 164, 587.
5. 4. Doherty, A. M. J. Med. Chem. 1992, 35, 1493.
6. 5. (a) Arai, H.; Hori, S.; Aramori, H.; Ohkubo, H.; Nakanishi, S. Nature (London), 1990, 348, 730;
7. (b) Sakuri, T.; Yanigasawa, M.; Takuwa, Y.; Miyazaki, H.; Kimura, S.; Goto, K.; Masaki, I. Nature (London) 1990, 348, 732;
8. (c) Karne, S.; Jayawickreme, C. K.; Lerner, M. R. J. Biol. Chem. 1993, 268, 19126.
9. 6. For reviews see: (a) Doherty, A. M. Annu. Rep. Med. Chem. 1991, 26, 83; 1992, 27, 79;
10. 6. For reviews see: (a) Doherty, A. M. Annu. Rep. Med. Chem. 1991, 26, 83; 1992, 27, 79;
11. (b) Spellmeyer, D. C. Annu. Rep. Med. Chem. 1994, 29, 65;
12. (c) Walsh, T. F. Annu. Rep. Med. Chem. 1995, 30, 91.
13. 7. Chan, M. F.; Okun, I.; Stavros, F. L.; Hwang, E.; Wolff, M. E.; Balaji, V. N. Biochem. Biophys. Res. Commun. 1994, 201, 228.
14. 8. Verner, E. J.; Kois, A.; Raju, B.; Wu, C.; Venkatachalapathi, Y. V.; Castillo, R.; Hwang, E.; Okun, I.; Stavros, F. D.; Balaji, V. N.; Wolff, M. E.; Chan, M. F. 208th ACS National Meeting, Washington, D.C., August 21-25, 1994, Abstract MEDI 215. A full account of this work has been submitted to Bioorg. Med. Chem. for publication.
15. 8. Verner, E. J.; Kois, A.; Raju, B.; Wu, C.; Venkatachalapathi, Y. V.; Castillo, R.; Hwang, E.; Okun, I.; Stavros, F. D.; Balaji, V. N.; Wolff, M. E.; Chan, M. F. 208th ACS National Meeting, Washington, D.C., August 21-25, 1994, Abstract MEDI 215. A full account of this work has been submitted to Bioorg. Med. Chem. for publication.
16. 9. (a) Stein, P. D.; Hunt, J. T.; Floyd, D. M.; Moreland, S.; Dickinson, K. E.; Mitchell, C., Liu, E. C.-K.; Webb, M. L.; Murugesan, N.; Dickey, J.; McMullen, D.; Zhang, R.; Lee, V. G.; Serafino, R.; Delaney, C.; Schaeffer, T. R.; Kozlowski, M. J. Med. Chem. 1994, 37, 329;
17. (b) Stein, P. D.; Floyd, D. M.; Bishaha, S., Dickey, J.; Girotra, R. N.; Gougoutas, J. Z.; Kozlowski, M; Lee, V. G.; Liu, E. C.-K.; Malley M. F.; McMullen, D.; Mitchell, C.; Moreland, S.; Murugesan, N.; Serafino, R.; Webb, M L.; Zhang, R.; Hunt, J. T. J. Med. Chem. 1995, 38, 1344.
18. 12 mp 67-69 °C]
19. 11. Stavros, F. D.; Hasel, K. W.; Okun, I.; Baldwin, J.; Freriks, K. J. Cardiovasc. Pharmacol. 1993, 22, S34.
20. 12. Brantley, R. K. U.S. Patent 3,547,940 (1967).