Pseudotheonamides, serine protease inhibitors from the marine sponge Theonella swinhoei

Journal of the American Chemical Society

Volumn 121, Issue 11, 1999, Pages 2425-2431

  Nakao, Yoichi ^a   Masuda, Akito ^a   Matsunaga, Shigeki ^a   Fusetani, Nobuhiro ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ARGININE; CYCLOTHEONAMIDE A; DIHYDROCYCLOTHEONAMIDE A; IMIDAZOLE DERIVATIVE; PIPERAZINE DERIVATIVE; PSEUDOTHEONAMIDE A1; PSEUDOTHEONAMIDE A2; PSEUDOTHEONAMIDE B2; PSEUDOTHEONAMIDE C; PSEUDOTHEONAMIDE D; PSEUDOTHEONAMIDE DERIVATIVE; SERINE PROTEINASE INHIBITOR; TYROSINE; UNCLASSIFIED DRUG;

ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; SPONGE (PORIFERA); STEREOCHEMISTRY;

EID: 0033599492     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9831195     Document Type: Article

References (19)

1. Bioactive Marine Metabolites. Part 86. Part 85: Tsukamoto, S.; Matsunaga, S.; Fusetani, N. J. Nat. Prod., in press.
2. (a) Fusetani, N.; Matsunaga, S.; Matsumoto, H.; Takebayashi, Y. J. Am. Chem. Soc. 1990, 112, 7053-7054.
3. (b) Nakao, Y.; Matsunaga, S.; Fusetani, N. Bioorg. Med. Chem. 1995, 3, 1115-1122.
4. (c) Nakao, Y.; Oku, N.; Matsunaga, S.; Fusetani, N. J. Nat. Prod. 1998, 61, 667-670.
5. (a) Maryanoff, B. E.; Qiu, X.; Padmanabhan, K. P.; Tulinsky, A.; Almond, Jr. H. R.; Andrade-Gordon, P.; Greco, M. N.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H.; Fusetani, N. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 8048-8052.
6. (b) Lee, A. Y.; Hagihara, M.; Karmacharya, R., Albers, M. W.; Schreiber, S. L.; Clardy, J. J. Am. Chem. Soc. 1993, 115, 12619-12620.
7. (c) Maryanoff, B. E.; Greco, M. N.; Zhang, H.; Andrade-Gordon, P.; Kauffman, J. A.; Nicolaou, K. C.; Liu, A.; Brungs, P. H. J. Am. Chem. Soc. 1995, 117, 1225-1239.
8. (d) Ganesh, V.; Lee, A. Y.; Clardy, J.; Tulinsky, A. Protein Sci. 1996, 5, 825-835.
9. 2 based on the same stereochemistry of the piperazinone moiety as in 2.
10. Summers, M. F.; Marzilli, L. G.; Bax, A. J. Am. Chem. Soc. 1986, 108, 4285-4294.
11. Bax, A.; Summers, M. F. J. Am. Chem. Soc. 1986, 108, 2093-2094.
12. March, J. Advanced Organic Chemistry; Willey-Interscience: New York, 1992; p 768.
13. Bax, A.; Azolos, A.; Dinya, Z.; Sudo, K. J. Am. Chem. Soc. 1986, 108, 8056-8063.
14. Edgar, G.; Hinegardner, W. S. J. Biol. Chem. 1923, 56, 881-886.
15. Deslongchamps, P. Stereoelectronic Effects in Organic Chemistry, Pergamon: Oxford, 1983; pp 4-21.
16. Marfey, P. Carlsberg Res. Commun. 1984, 49, 591-596.
17. Matsunaga, S.; Fusetani, N. J. Org. Chem. 1995, 60, 1177-1181.
18. Dondoni, A.; Fantin, G.; Fogagnolo, M.; Pedrini, P. J. Org. Chem. 1990, 55, 1439-1446.
19. Maryanoff, B. E.; Zhang, H.; Greco, M. N.; Zhang, E.; Vanderhoff-Hanaver, P.; Tulinsky, A. Tetrahedron Lett. 1996, 37, 3667-3670.