Monamphilectine A, a potent antimalarial β-lactam from marine sponge hymeniacidon sp: Isolation, structure, semisynthesis, and bioactivity

Organic Letters

Volumn 12, Issue 22, 2010, Pages 5290-5293

  Avilés, Edward ^a   Rodríguez, Abimael D ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; AMPICILLIN; ANTIMALARIAL AGENT; BETA LACTAM; CARBENICILLIN; CHLOROQUINE; DITERPENE;

ANIMAL; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG RESISTANCE; ESCHERICHIA COLI; ISOLATION AND PURIFICATION; MARINE BIOLOGY; MICROBIOLOGICAL EXAMINATION; PLASMODIUM FALCIPARUM; SPONGE (PORIFERA); SYNTHESIS;

ALKALOIDS; AMPICILLIN; ANIMALS; ANTIMALARIALS; BETA-LACTAMS; CARBENICILLIN; CHLOROQUINE; DITERPENES; DRUG RESISTANCE; ESCHERICHIA COLI; MARINE BIOLOGY; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PLASMODIUM FALCIPARUM; PORIFERA;

EID: 78449270839     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol102351z     Document Type: Article

References (24)

1. Kar, S.; Kar, S. Nat. Rev. Drug Discovery 2010, 9, 511-512
2. Na-Bangchang, K.; Karbwang, J. Fundam. Clin. Pharmacol. 2009, 23, 387-409
3. Enserink, M. Science 2010, 328, 844-846
4. Kappe, S. H. I.; Vaughan, A. M.; Boddey, J. A.; Cowman, A. F. Science 2010, 328, 862-866
5. Laport, M. S.; Santos, O. C. S.; Muricy, G. Curr. Pharm. Biotechnol. 2009, 10, 86-105
6. Wratten, S. J.; Faulkner, D. J.; Hirotsu, K.; Clardy, J. Tetrahedron Lett. 1978, 4345-4348
7. 2 425.3042).
8. For a review on marine isonitriles, see
9. Garson, M. J.; Simpson, J. S. Nat. Prod. Rep. 2004, 21, 164-179
10. Amphilectane-based isonitriles have been isolated also from the marine sponges Cymbastela hooperi, Cribochalina sp., and Ciocalapata sp., see
11. König, G. M.; Wright, A. D.; Angerhofer, C. K. J. Org. Chem. 1996, 61, 3259-3267
12. Ciavatta, M. L.; Fontana, A.; Puliti, R.; Scognamiglio, G.; Cimino, G. Tetrahedron 1999, 55, 12629-12636
13. Wattanapiromsakul, C.; Chanthathamrongsiri, N.; Bussarawit, S.; Yuenyongsawad, S.; Plubrukarn, A.; Suwanborirux, K. Can. J. Chem. 2009, 87, 612-618
14. Prior to this report, only six marine β-lactams (all isolated from the marine bryozoan Chartella papyracea) have been described, see
15. Chevolot, L.; Chevolot, A.-M.; Gajhede, M.; Larsen, C.; Anthoni, U.; Christophersen, C. J. Am. Chem. Soc. 1985, 107, 4542-4543
16. Anthoni, U.; Chevolot, L.; Larsen, C.; Nielsen, P. H.; Christophersen, C. J. Org. Chem. 1987, 52, 4709-4712
17. Anthoni, U.; Bock, K.; Chevolot, L.; Larsen, C.; Nielsen, P. H.; Christophersen, C. J. Org. Chem. 1987, 52, 5638-5639
18. Ciavatta, M. L.; Gavagnin, M.; Manzo, E.; Puliti, R.; Mattia, C. A.; Mazzarella, L.; Cimino, G.; Simpson, J. S.; Garson, M. J. Tetrahedron 2005, 61, 8049-8053
19. For a review, see
20. Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168-3210
21. Dömling, A.; Kehagia, K.; Ugi, I. Tetrahedron 1995, 51, 9519-9522
22. Gedey, S.; Van der Eycken, J.; Fülöp, F. Org. Lett. 2002, 4, 1967-1969
23. 50 = 0.30 μM. For pioneering research on the antimalarial activity of terpene isonitriles from sponges, see
24. Wright, A. D.; Wang, H.; Gurrath, M.; König, G. M.; Kocak, G.; Neumann, G.; Loria, P.; Foley, M.; Tilley, L. J. Med. Chem. 2001, 44, 873-885