Amphimic acids and related long-chain fatty acids as DNA topoisomerase I inhibitors from an Australian sponge, Amphimedon sp.: Isolation, structure, synthesis, and biological evaluation

Tetrahedron

Volumn 53, Issue 49, 1997, Pages 16699-16710

  Nemoto, Takayuki ^a   Yoshino, Go ^a   Ojika, Makoto ^a   Sakagami, Youji ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

DNA TOPOISOMERASE INHIBITOR; LONG CHAIN FATTY ACID; NATURAL PRODUCT;

ARTICLE; DEGRADATION; DRUG ACTIVITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; PRIORITY JOURNAL; SPECTROSCOPY; SPONGE (PORIFERA); STEREOCHEMISTRY;

AMPHIMEDON; PORIFERA;

EID: 0030807806     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)10099-0     Document Type: Article

References (23)

1. Ojika, M.; Yoshino, G.; Sakagami, Y. Tetrahedron Lett. 1997, 38, 4235-4238.
2. Nemoto, T.; Ojika, M.; Sakagami, Y. Tetrahedron Lett. 1997, 38, 5667-5670.
3. Tomer, K. B.; Crow, F. W.; Gross, M. L. J. Am. Chem. Soc. 1983, 105, 5487-5488.
4. Litchfield, C.; Marcantonio, E. E. Lipids 1978, 13, 199-202.
5. Ayanoglu, E.; Rizzolio, M.; Beaulieu, S.; Roberts, J.; Oz, O.; Djerassi, C. Comp. Biochem. Physiol. 1990, 96B, 597-603.
6. Carballeira, N. M.; Shalabi, F.; Maldonado, M. E. Lipids 1990, 25, 235-237.
7. Carballeira, N. M.; Maldonado, M. E. Lipids 1989, 24, 371-374.
8. Ayanoglu, E.; Walkup, R., D.; Sica, D.; Djerassi, C. Lipids 1982, 17, 617-625.
9. (a) Bestmann, H.-J.; Denzel, T. Tetrahedron Lett. 1966, 3591-3593.
10. (b) Utimoto, K.; Tamura, M.; Sisido, K. Tetrahedron 1973, 29, 1169-1171.
11. (c) Crawford, R. J.; Tokunaga, H.; Schrijver, L. M. H. C.; Godard, J. C.; Nakashima, T. Can. J. Chem. 1978, 56, 992-997.
12. Smolic, S.; Kvita, V.; Weichet, J.; Trcka, V. Collect. Czech. Chem. Commun. 1960, 25, 259-264.
13. Finan, J. M.; Kishi, Y. Tetrahedron Lett. 1982, 23, 2719-2722.
14. (a) Buss, A. D.; Warren, S. J. Chem. Soc. Perkin Trans. I 1985, 2307-2325.
15. (b) Buss, A. D; Warren S. J. Chem. Soc., Chem. Commun. 1981, 100-101.
16. Tamura, H.; Kohchi, C.; Yamada, R.; Ikeda, T.; Koiwai, O.; Patterson, E; Keene, J. D.; Okada, K.; Kjeldsen, E.; Nishikawa, K.; Andoh, T. Nucleic Acids Res. 1991, 19, 69-75.
17. Hsiang, Y.-H.; Hertzberg, R.; Hecht, S.; Liu, L. F. J. Biol. Chem. 1985, 260, 14873-14878.
18. Tamura, H.; Ikegami, Y.; Ono, K.; Sekimizu, K.; Andoh, T. FEBS Lett. 1990, 261, 151-154.
19. For example, (a) Barnathan, G.; Kornprobst, J. -M.; Doumenq, P.; Miralles, J. Lipids 1996, 31, 193-200.
20. (b) Carballeira, N. M.; Shalabi, F. J. Nat. Prod. 1994, 57, 1152-1159.
21. (c) Christie, W. W.; Brechany, E. Y.; Marekov, I. N.; Stefanov, K. L.; Andreev, S. N. Comp. Biochem. Physiol. 1994, 109B, 245-252.
22. Hill, J. G.; Rossiter, B. E.; Sharpless, K. B. J. Org. Chem. 1983, 48, 3607-3608.
23. Kraus, G. A.; Taschner, M. J. J. Org. Chem. 1980, 45, 1175-1176.