Analogs of an endothelin antagonist RES-701-1: Substitutions of C-terminal amino acid

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 7, 1996, Pages 775-778

  Shibata, Kenji ^a   Yano, Keiichi ^a   Tanaka, Takeo ^a   Matsuda, Yuzuru ^a   Yamasaki, Motoo ^a  

^a KYOWA HAKKO KOGYO CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ENDOTHELIN B RECEPTOR; ENDOTHELIN RECEPTOR ANTAGONIST; RES 701 1;

AMINO ACID SEQUENCE; ANIMAL TISSUE; ARTICLE; CATTLE; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; LUNG; MASS SPECTROMETRY; NONHUMAN; PEPTIDE SYNTHESIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0030003612     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00127-8     Document Type: Article

References (20)

1. For reviews, see; a) Simonson, M. S.; Dunn, M. J. Hypertension 1991, 17, 856.
2. b) Rubanyi, G. M.; Parker Botelho, L. H. FASEB J. 1991, 5, 2713.
3. Yanagisawa, M.; Kurihara, H.; Kimura, S.; Tomobe, Y.; Kobayashi, M.; Mitsui, Y.; Yazaki, Y.; Goto, K.; Masaki, T. Nature 1988, 332, 411.
4. For reviews, see; a) Miller, R. C., Pelton, J. T.; Huggins, J. P. Trends Pharmacol. Sci. 1993, 14, 54.
5. b) Bax, W. A.; Saxena, P. R. ibid. 1994, 15, 379.
6. Haynes, W. G.; Davenport, A. P.; Webb, D. J. ibid. 1993, 14, 225.
7. Morishita, Y; Chiba, S.; Tsukuda, E.; Tanaka, T.; Ogawa, T.; Yamasaki, M.; Yoshida, M.; Kawamoto, I.; Matsuda, Y. J. Antibiot. 1994, 47, 269.
8. Yamasaki, M.; Yano, K.; Yoshida, M.; Matsuda, Y.; Yamaguchi, K. J. Antibiot. 1994, 47, 276.
9. 16]RES-701-1. a) Ogawa, T.; Ochiai, K.; Tanaka, T.; Tsukuda, E.; Chiba, S.; Yano, K.; Yamasaki, M.; Yoshida, M.; Matsuda, Y. J. Antibiot. 1995, 48, 1213.
10. b) Yano, K.; Yamasaki, M.; Yoshida, M.; Matsuda, Y.; Yamaguchi, K. J. Antibiot. 1995, 48, 1368.
11. Kimura, S.; Kasuya, Y.; Sawamura, T.; Shinmi, O.; Sugita, Y.; Yanagisawa, M.; Goto, K.; Masaki, M. Biochem. Biophys. Res. Commun. 1988, 156, 1182.
12. The Peptides. Analysis, Synthesis, Biology ; Gross, E.; Meienhofner, J., Ed.; Academic Press: New York, 1979.
13. Anwer, M. K.; Spatola, A. F. Synthesis 1980, 929.
14. Because of very small scale preparations (∼100μg), absorption of the products to palladium on carbon let the yields lower.
15. Tanaka, T.; Tsukuda, E.; Nozawa, M.; Nonaka, H.; Ohno, T.; Kase, H.; Yamada, K.; Matsuda, Y. Mol. Pharmacol. 1994, 45, 724.
16. a) Nicholson, G.; Frank, H. J. High Resolut. Chromatogr. and Chromatogr. Commun. 1979, 2, 411.
17. b) Abe, I.; Musha, S. J. Chromatogr. 1980, 200, 195.
18. RES-701-1 has a extraordinary folded rigid structure, which tail portion passes through inside of the ring. Katahira, R.; Shibata, K.; Yamasaki, M.; Matsuda, Y.; Yoshida, M. Bioorg. Med. Chem. 1995, 3, 1273.
19. 16] analog (ref. 13 and unpublished result).
20. Compounds 3∼7 were generated as exclusively single products by HPLC analyses. It can not be proved why so evident epimerizations occurred only in the case of Trp-condensations. It is presumed for one reason that the Trp-condensation reactions were very slow compared to other amino acids used here.