Sulfated meroterpenoids from the Brazilian sponge Callyspongia sp. are inhibitors of the antileishmaniasis target adenosine phosphoribosyl transferase

Journal of Organic Chemistry

Volumn 71, Issue 23, 2006, Pages 8685-8690

  Gray, Christopher A ^a   De Lira, Simone P ^b   Silva, Marcio ^b   Pimenta, Eli F ^b   Thiemann, Otavio H ^b   Oliva, Glaucius ^b   Hajdu, Eduardo ^c   Andersen, Raymond J ^a   Berlinck, Roberto G S ^b  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b UNIVERSITY OF SÃO PAULO   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DATA REDUCTION; ENZYME INHIBITION; ENZYMES; NUCLEAR MAGNETIC RESONANCE; OLEFINS;

CARBON SKELETONS; DISULFATED MEROTERPENOIDS; LEISHMANIA;

NITROGEN COMPOUNDS;

ADENINE PHOSPHORIBOSYLTRANSFERASE; ILHABELANOL; ILHABRENE; ISOAKATERPIN; MEROTERPENOID DERIVATIVE; SULFUR DERIVATIVE; TERPENOID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CALLYSPONGIA; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; IC 50; LEISHMANIASIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; SPONGE (PORIFERA); STRUCTURE ANALYSIS;

ADENINE PHOSPHORIBOSYLTRANSFERASE; ANIMALS; CALLYSPONGIA; ENZYME INHIBITORS; LEISHMANIA; MOLECULAR CONFORMATION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TERPENES;

EID: 33750888881     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060295k     Document Type: Article

References (23)

1. (a) Gramkcia, M.; Gradoni, L. Int. J. Parasitol. 2005, 35, 1169-1180.
2. (b) Davis, A. J.; Murray, H. W.; Handman, E. Trends Parasitol. 2004, 20, 73-76.
3. (c) Croft, S. L.; Barrett, M. P.; Urbina, J. A. Trends Parasitol. 2005, 21, 508-512.
4. (d) Croft, S. L.; Coombs, G. H. Trends Parasitol. 2003, 19, 502-508.
5. Chan-Bacab, M. J.; Peña-Rodríguez, L. J. Nat. Prod. Rep. 2001, 18, 674-688.
6. Silva, M.; Silva, C. H. T. P.; Iulek, J.; Oliva, G.; Thiemann, O. H. Biochim. Biophys. Acta 2004, 1696, 31-39.
7. Marr, J. J. J. Lab. Clin. Med. 1991, 118, 111-119.
8. Stonik, V. A.; Makarieva, T. N.; Dmitrenok, A. S. J. Nat. Prod. 1992, 55, 1256-1260.
9. Isaacs, S.; Kashman, Y. Tetrahedron Lett. 1992, 33, 2227-2230.
10. Isaacs, S.; Hizi, A.; Kashman, Y. Tetrahedron 1993, 49, 4275-4282.
11. Loya, S.; Tal, R.; Hizi, A.; Issacs, S.; Kashman, Y.; Loya, Y. J. Nat. Prod. 1993, 56, 2120-2125.
12. Fukami, A.; Ikeda, Y.; Kondo, S.; Naganawa, H.; Takeuchi, T.; Furuya, S.; Hirabayashi, Y.; Shimoike, K.; Hosaka, S. Tetrahedron Lett. 1997, 38, 1201-1202.
13. Blackburn, C. L.; Hopmann, C.; Sakowicz, R.; Berdelis, M. S.; Goldstein, L. S. B.; Faulkner, D. J. J. Org. Chem. 1999, 64, 5565-5570.
14. Blackburn, C. L.; Faulkner, D. J. Tetrahedron 2000, 56, 8429-8432.
15. Castro, J. M.; Salido, S.; Altarejos, J.; Nogueros, M.; Sanchez, A. Tetrahedron 2002, 58, 5941-5949.
16. Akita, H.; Nozawa, M.; Shimizu, H. Tetrahedron: Asymmetry 1998, 9, 1789-1799.
17. Kawai, N.; Takao, K. I.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 4193-4196.
18. Kawai, N.; Fujibayashi, Y.; Kuwabara, S.; Takao, K.; Ijuin, Y.; Kobayashi, S. Tetrahedron 2000, 56, 6467-6478.
19. Hattori, T.; Adachi, K.; Shizuri, Y. J. Nat. Prod. 1997, 60, 411-413.
20. Abdel-Kader, M.; Berger, J. M.; Slebodnick, C.; Hoch, J.; Malone, S.; Wisse, J. H.; Werkhoven, M. C. M.; Mamber, S.; Kingston, D. G. I. J. Nat. Prod. 2002, 65, 11-15.
21. (a) Silva, M.; Napolitano, H. B.; Ellena, J.; Rocha, W. C.; Vieira, P. C.; Oliva, G.; Thiemann, O. H. Acta Crystallogr. 2003, E59, 1575-1577.
22. (b) Napolitano, H. B.; Silva, M.; Ellena, J.; Rocha, W. C.; Vieira, P. C.; Thiemann, O. H.; Oliva, G. Acta Crystallogr. 2003, E59, 1503-1505.
23. (c) Napolitano, H. B.; Silva, M.; Ellena, J.; Rocha, W. C.; Vieira, P. C.; Thiemann, O. H.; Oliva, G. Acta Crystallogr. 2003, E59, 1506-1508.