Pseudoceratidine, a marine natural product with antifouling activity: Synthetic and biological studies

Tetrahedron

Volumn 54, Issue 25, 1998, Pages 6977-6986

  Ponasik, James A ^a   Conova, Susan ^b   Kinghorn, Denise ^c   Kinney, William A ^c   Rittschof, Daniel ^b   Ganem, Bruce ^a  

^a Department of Molecular Biology and Genetics   (United States)

^b DUKE UNIVERSITY   (United States)

^c Genaera Corporation   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIFOULING AGENT; ANTIINFECTIVE AGENT; PSEUDOCERATIDINE; UNCLASSIFIED DRUG;

ACYLATION; ANTIMICROBIAL ACTIVITY; ARTICLE; BROMINATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY; PAINT INDUSTRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

EID: 0032543734     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00340-8     Document Type: Article

References (28)

1. 1. Layman, P. L. Chemical and Engineering News 1995, (May 1), 23.
2. 2. Iwata, H.; Tanabe, S.; Mizuno, T.; Tatsukawa, R. Environ. Sci. Tech. 1995, 29, 2959.
3. 3. Ohhira, S.; Matsui, H.; Nitta, K. Vet. Human Toxicol. 1996, 38, 206.
4. 4. Tsukamoto, S.; Kato, H.; Hiroka, H.; Fusetani, N. Tetrahedron Lett. 1996, 37, 1439.
5. 5. Tsukamoto, S.; Kato, H.; Hiroka, H.; Fusetani, N. Tetrahedron 1996, 52, 8181.
6. 6. Roll, D. M.; Chang, C. W. J.; Scheuer, P. J.; Gray, G. A.; Shoolery, J. N.; Matsumoto, G. K.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1985, 107, 2916.
7. 7. Tsukamoto, S.; Kato, H.; Hiroka, H.; Fusetani, N. J. Org. Chem. 1996, 61, 2936.
8. 8. Hamana, M. T.; Scheuer, P. J.; Kelly-Borges, M. J. Org. Chem. 1993, 58, 6565.
9. 9. (a) Ponasik, J. A.; Kassab, D. J.; Ganem, B. Tetrahedron Lett. 1996, 37, 6041;
10. (b) Behrens, C.; Christoffersen, M. W.; Gram, L.; Nielsen, P. H. Bioorg. Med. Chem. Lett. 1997, 7, 321.
11. 10. (a) Forenza, S.; Minale, L.; Riccio, R. J. Chem. Soc. Chem. Commun. 1971, 1129;
12. (b) Gunasekera, S. P.; Cranick, S.; Longley, R. E. J. Nat. Prod. 1989, 52, 757.
13. 11. Garcia, E. E.; Benjamin, L. E.; Fryer, R. I. J. Chem. Soc. Chem. Commun. 1973, 78.
14. 12. Walker, R. P.; Faulkner, D. J.; Van Engen, D.; Clardy, J. J. Am. Chem. Soc. 1981, 103, 6772.
15. 13. Anderson, H. J.; Lee, S.-F. Can. J. Chem. 1965, 43, 409.
16. 14. Hodge, P.; Rickards, R. W. J. Chem. Soc. 1965, 459.
17. 15. Joshua, A. V.; Scott, J. R. Tetrahedron Lett. 1984, 25, 5725.
18. 16. McManis, J. S.; Ganem, B. J. Org. Chem. 1980, 45, 2041.
19. 17. Takeuchi, T.; Saino, T.; Yoshida, M.; Takahashi, K.; Nakamura, T.; Umezawa, H. Eur. Pat. Appl. 1986, EP 241,797.
20. 18. Takeuchi, T.; Tomioshi, T.; Saino, T.; Takahashi, K.; Nakamura, T. Eur. Pat. Appl. 1989, EP 309,971.
21. 19. Schmitz, F. J.; Hollenbeak, K. H.; Prasad, R. S. Tetrahedron Lett. 1979, 3387.
22. 20. Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925.
23. 21. (a) Moore, K. S.; Wehrli, S.; Roder, H.; Rogers, M.; Forrest, Jr., J. N.; McCrimmon, D.; Zasloff, M. Proc. Natl. Acad. Sci. U. S. A. 1993, 90, 1354;
24. (b) Wehrli, S. L.; Moore, K. S.; Roder, H.; Durell, S.; Zasloff, M. Steroids 1993, 58, 370.
25. 22. "Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically," National Committee for Clinical Laboratory Standards, 3rd Ed.; Approved Standard M7-A3, NCCLS, Wayne PA, 1993.
26. 23. "Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeast," National Committee for Clinical Laboratory Standards; Tentative Standard M27-T, NCCLS, Wayne PA, 1995.
27. 24. Rittschof, D.; Clare, A. S.; Gerhart, D. J.; Sister Avelin Mary; Bonaventura, J. Biofouling 1992, 6, 115.
28. 25. Lieberman, H. R. Drug. Chem. Toxicol. 1983, 6, 111.