Amide bond surrogates: A study in thiophenesulfonamide eased endothelin receptor antagonists

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 7, 1997, Pages 939-944

  Raju, B ^a,b   Okun, Ilya ^a   Stavros, Fiona ^a,b   Chan, Ming Fai ^a  

^a ImmunoPharmaceutics Inc   (United States)

^b TEXAS BIOTECHNOLOGY CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIN A RECEPTOR; ENDOTHELIN B RECEPTOR; ENDOTHELIN RECEPTOR ANTAGONIST; SULFONAMIDE; THIOPHENE DERIVATIVE;

ARTICLE; BINDING AFFINITY; DRUG RECEPTOR BINDING; DRUG STABILITY; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; IN VITRO STUDY; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030899155     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)00133-9     Document Type: Article

References (22)

1. Presented in part at the ACS National Meeting, Louisiana, New Orleans, April, 1996, Abstract MEDI 147.
2. (a) Yanagisawa, M.; Kurihra, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitisui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. Nature (London) 1988, 332, 411;
3. (b) Inoue, A.; Yanagisawa, M.; Kimura, S.; Kasuya, Y.; Miyauichi, S.; Goto, K.; Masaki, T. Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 2863;
4. (c) Shinmi, O.; Kimura, S.; Sawamura, T.; Sugita, Y.; Yoshizawa, T. Biochem. Biophys. Res. Commun. 1989, 164, 587.
5. Wolłberg, Z.; Shabo-Shina, R.; Intrator, N.; Bdolah, A.; Kochva, E.; Shavit, G.; Oron, Y.; Vidne, B. A.; Gitter, S. Toxicon 1988, 26, 525.
6. Endothelin receptors: From the Gene to the Human; Ruffolo Jr, R. R., Ed.; CRC: Florida, 1995; pp 1-271.
7. (a) Arai, H.; Hori, S.; Aramori, I.; Ohkubo, H.; Nakanishi, S. Nature (London) 1990, 348, 730;
8. (b) Sakurai, T.; Yanagisawa, M.; Takuwa, Y.; Miyazaki, H.; Kimura, S.; Goto, K.; Masaki, T. Nature (London) 1990, 348, 732;
9. (c) Karne, S.; Jayawickreme, C. K.; Lerner, M. R. J. Biol. Chem. 1993, 268, 19126.
10. (a) Raju, B.; Wu, C.; Kois, A.; Verner, E. J.; Okun, I.; Stavros, F. D.; Chan, M. F. Bioorg. Med. Chem. Lett. 1996, 6, 2651;
11. (b) Raju, B.; Wu, C.; Castillo, R.; Okun, I.; Stavros, F. D.; Chan, M. F. Abstracts of Papers, 211th National Meeting Of the American Chemical Society, New Orleans, LA; American Chemical Society: Washington, DC, 1996; Abstract MEDI 145;
12. (c) Wu, C.; Raju, B.; Stavros, F. D.; Okun, I.; Castillo, R.; Chan, M. F. J. Med. Chem. submitted;
13. (d) Raju, B.; Okun, I.; Stavros, F. D.; Chan, M. F. Bioorg. Med. Chem. Lett. preceding article in this issue;
14. (e) Chan, M. F.; Raju, B.; Kois, A.; Castillo, R. S.; Verner, E. J.; Wu, C.; Hwang, E.; Okun, I.; Stavros, F. D.; Balaji, V. N. Bioorg. Med. Chem. Lett. 1996, 6, 2393;
15. (f) For reviews see: Walsh, T. F. Annu. Rep. Med. Chem. 1995, 30, 91; and references cited therein;
16. (g) Battistini, B.; Botting, R. Drugs News and Perspectives. 1995, 8, 365.
17. Greene, T. W.; Wuts, P. G. In Protective Groups in Organic Synthesis; John Wiley: New York, 1991; 379.
18. Kellog, R. M.; Schapp, A. P.; Harper, E. T.; Wynberg, H.; J. Org. Chem. 1968, 33, 2902.
19. 3CN (Linear gradient) over 30 min period.
20. (a) Stavros, F. D.; Hasel, K. W.; Okun, I.; Baldwin, J.; Feriks, K. J. Cardivasc. Pharmacol. 1993, 22, S34;
21. (b) Chan, M. F.; Okun, I.; Stavros, F. D.; Hwang, E.; Wolff, M. E.; Balaji, V. N. Biochem. Biophys. Res. Commun. 1994, 201, 228.;
22. (c) Binding assays were conducted at 24°C.