Merobatzelladines A and B, anti-infective tricyclic guanidines from a marine sponge monanchora sp.

Organic Letters

Volumn 11, Issue 12, 2009, Pages 2655-2658

  Takishima, Shunsuke ^a   Ishiyama, Aki ^b   Iwatsuki, Masato ^b   Otoguro, Kazuhiko ^b   Yamada, Haruki ^b   Õmura, Satoshi ^b   Kobayashi, Hirotsugu ^a   Van Soest, Rob W M ^c   Matsunaga, Shigeki ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b KITASATO UNIVERSITY   (Japan)

^c UNIVERSITY OF AMSTERDAM   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIINFECTIVE AGENT; GUANIDINE DERIVATIVE; MEROBATZELLADINE A; MEROBATZELLADINE B; POLYCYCLIC HYDROCARBON;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ISOLATION AND PURIFICATION; SPONGE (PORIFERA); STEREOISOMERISM;

ANIMALS; ANTI-INFECTIVE AGENTS; GUANIDINES; MOLECULAR STRUCTURE; POLYCYCLIC COMPOUNDS; PORIFERA; STEREOISOMERISM;

EID: 67149146451     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9006794     Document Type: Article

References (23)

1. Donia, M.; Hamann, M. T. Lancet Infect. Dis. 2003, 3, 338-348.
2. Kobayashi, H.; Miyata, Y.; Okada, K.; Fujita, T.; Iwashita, T.; Nakao, Y.; Fusetani, N.; Matsunaga, S. Tetrahedron 2007, 63, 6748-6754.
3. The major cytotoxic constituent of this sponge was identified as azaspiracid-2.4 A reexamination of the sponge in ref 4 indicated that the taxonomy of the sponge should be corrected from Echinoclathria sp. to Monanchora sp.
4. Ueoka, R.; Ito, A.; Izumikawa, M.; Maeda, S.; Takagi, M.; Shinya, K.; Yoshida, M.; van Soest, R. W. M.; Matsunaga, S. Toxicon 2009, 53, 680-684.
5. Kupchan, S. M.; Britton, R. W.; Ziegler, M. F.; Sigel, C. W. J. Org. Chem. 1973, 38, 178-179.
6. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, 1990; pp 192-194.
7. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy; VCH: Weinheim, 1990; pp 236-238.
8. Heys, L.; Moore, C. G.; Murphy, P. J. Chem. Soc. Rev. 2000, 29, 51-61.
9. (a) Nagasawa, K.; Koshino, H.; Nakata, T. Tetrahedron Lett. 2001, 42, 4155-4158
10. (b) Snider, B. B.; Busuyek, M. V. J. Nat. Prod. 1999, 62, 1707-1711
11. (c) Cohen, F.; Overman, L. E. J. Am. Chem. Soc. 2001, 123, 10782-10783.
12. Snider, B.; Chen, J. Tetrahedron Lett. 1996, 39, 6977-6980.
13. Wang, Q.; Lonnberg, H. J. Am. Chem. Soc. 2006, 128, 10716-10728.
14. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113, 4092-4096.
15. Oku, N.; Matsunaga, S.; Wada, S.; Watabe, S.; Fusetani, N. J. Nat. Prod. 2000, 63, 205-209.
16. Kobayashi, M.; Aoki, S.; Kitagawa, I. Tetrahedron Lett. 1994, 35. 1243-1246,
17. Otoguro, K.; Ishiyama, A.; Namatame, M.; Nishihara, A.; Furusawa, T.; Masuma, R.; Shiomi, K.; Takahashi, Y.; Yamada, H.; Omura, S. J. Antibiot. 2008, 61, 372-378.
18. Otoguro, K.; Kohana, A.; Manabe, C.; Ishiyama, A.; Ui, H.; Shiomi, K.; Yamada, H.; Omura, S. Antibiot. 2001, 54, 658-663.
19. Berlinck, R. G. S.; Burtoloso, A. C. B.; Kossuga, M. H. Nat. Prod. Rep 2008, 25. 919-954. and previous reviews in the series,
20. Chang, L. C.; Whittaker, N. F.; Bewley, C. A. INat. Prod. 2003, 66, 1490-1494.
21. Hua, H.-M.; Peng, J.; Dunbar, D. C.; Schinazi, R. R.; Andrew, A. G.; de, C: Cuevas, C.; Garcia-Fernandez, L. R: Kelly, M.; Hamann, M. T. Teu-ahedron 2007, 63. 11179-11188.
22. Yu, M.; Pochapsky, S. S.; Snider, B. B. JJ)rg. Chem. 2008, 73, 9065-9074,
23. Cohen, R.; Overman, L. E. L Am. Chem. Soc. 2006, 128, 2594-2603.