Characterization of the main radical and products resulting from a reductive activation of the antimalarial arteflene (Ro 42-1611)

Journal of Organic Chemistry

Volumn 64, Issue 18, 1999, Pages 6776-6781

  Cazelles, Jérôme ^a   Robert, Anne ^a   Meunier, Bernard ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEFLENE; ARTEMISIN DERIVATIVE; PLANT EXTRACT;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG ISOLATION; DRUG MECHANISM; DRUG STRUCTURE; MALARIA; NONHUMAN; PHYTOTHERAPY; PLANT; PLASMODIUM FALCIPARUM;

EID: 0032886808     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990744z     Document Type: Article

References (38)

1. Klayman, D. L. Science 1985, 228, 1049-1055.
2. Meshnick, S. R.; Taylor, T. E.; Kamchonwongpaisan, S. Microbiol. Rev. 1996, 60, 301-315.
3. Kamchonwongpaisan, S.; Meshnick, S. R. Gen. Pharmacol. 1696, 27, 587-592.
4. Krungkrai, S. R.; Yuthavong, Y. Trans. R. Soc. Trop. Med. Hyg. 1987, 81, 710-714.
5. Cumming, J. N.; Ploypradith, P.; Posner, G. H. Adv. Pharmacol. 1997, 37, 253-297.
6. Posner, G. H.; Oh, C. H.; Wang, D.; Gerena, L.; Milhous, W. K.; Meshnick, S. R.; Asawamahasakda, W. J. Med. Chem. 1994, 37, 1266-1258.
7. Hong, Y.-L.; Yang, Y.-Z.; Meshnick, S. R. Mol. Biochem. Parasitol. 1994, 63, 121-128.
8. Asawamahasakda, W.; Ittarat, I.; Pu, Y.-M.; Ziffer, H.; Meshnick, S. R. Antimicrob. Agents Chemother. 1994, 38, 1854-1858.
9. Meshnick, S. R. Lancet 1994, 344, 1441-1442.
10. Jefford, C. W.; Kohmoto, S.; Jaggi, D.; Timari, G.; Rossier, J.-C.; Rudaz, M.; Barbuzzi, O.; Gérard, D.; Burger, U.; Kamalaprrja, P.; Mareda, J.; Bernardinelli, G.; Manzanares, I.; Canfield, C. J.; Fleck, S. L.; Robinson, B. L.; Peters, W. Helv. Chim. Acta 1995, 78, 647-662.
11. Robert, A.; Meunier, B. J. Am. Chem. Soc. 1997, 119, 5968-5969.
12. Robert, A.; Meunier, B. Chem. Eur. J. 1998, 4, 1287-1296.
13. Robert, A.; Meunier, B. Chem. Soc. Rev. 1998, 27, 273-279.
14. Jefford, C. W. Adv. in Drug Res. 1997, 29, 271-325.
15. Torok, D. S.; Ziffer, H.; Meshnick, S. R.; Pan, X.-Q. J. Med. Chem. 1965, 38, 5045-5050.
16. Lin, A. J.; Zikry, A. B.; Kyle, D. E. J. Med. Chem. 1897, 40, 1396-1400.
17. Avery, M. A.; Fan, P.; Karle, J. M.; Miller, R.; Goins, K. Tetrahedron Lett. 1995, 36, 3965-3968.
18. Posner, G. H.; Cumming, J. N.; Woo, S.-H.; Ploypradith, P.; Xie, S.; Shapiro, T. A. J. Med. Chem. 1998, 41, 940-951.
19. Cumming, J. N.; Wang, D.; Park, S. B.; Shapiro, T. A.; Posner, G. H. J. Med. Chem. 1998, 41, 952-964.
20. Kamchonwongpaisan, S.; Nilanonta, C.; Tarnchompoo, B.; Thebtaranonth, C.; Thebtaranonth, Y.; Yuthavong, Y.; Kongsaeree, P.; Clardy J. Tetrahedron Lett. 1995, 36, 1821-1824.
21. Zhang, L.; Zhou, W.-S.; Xu, X.-X. J. Chem. Soc., Chem. Commun. 1988, 523-524.
22. Hofheinz, W.; Bürgin, H.; Gocke, E.; Jaquet, C.; Masciadri, R.; Schmid, G.; Stohler, H.; Urwyler, H. Trop. Med. Parasitol. 1994, 45, 261-265.
23. Jaquet, C.; Stohler, H. R.; Chollet, J.; Peters, W. Trop. Med. Parasitol. 1994, 45, 266-271.
24. Weidekamm, E.; Dumont, E.; Jaquet, C. Trop. Med. Parasitol. 1994, 45, 278-283 and references therein.
25. Hoffmann, P.; Robert, A.; Meunier, B. Bull. Soc. Chim. Fr. 1992, 129, 85-97.
26. Jacobsen, E. N.; Deng, L.; Furukawa, Y.; Martinez, L. E. Tetrahedron 1994, 50, 4323-4334.
27. Sullivan, D. J., Jr.; Gluzman, I. Y.; Goldberg, D. E. Science 1996, 271, 219-222.
28. O'Neill, P. M.; Bishop, L. P.; Searle, N. L.; Maggs, J. L.; Ward, S. A.; Bray, P. G.; Storr, R. C.; Park, B. K. Tetrahedron Lett. 1997, 38, 4263-4266.
29. Posner, G. H.; Cumming, J. N.; Ploypradith, P.; Oh, C. H. J. Am. Chem. Soc. 1995, 117, 5885-5886.
30. Jefford, C. W.; Vicente, M. G. H.; Jacquier, Y.; Favarger, F.; Mareda, J.; Millasson-Schmidt, P.; Brunner, G.; Burger, U. Helv. Chim. Acta 1996, 79, 1475-1487.
31. Haynes, H. K.; Vonwiller, S. C. Tetrahedron Lett. 1996, 37, 257-260.
32. Chateauneuf, J.; Lusztyk, J.; Ingold, K. U. J. Org. Chem. 1988, 53, 1629-1632.
33. Root, K. S.; Hill, C. H.; Lawrence, L. M.; Whitesides, G. M. J. Am. Chem. Soc. 1988, 111, 5405-5412.
34. Chérest, M.; Felkin, H. Tetrahedron Lett. 1968, 2205-2208
35. Schauble, J. H.; Walter, G. J.; Morin, J. G. J. Org. Chem. 1974, 39, 755-760.
36. Giese, B. Angew. Chem., Int. Ed. Engl. 1983, 22, 753-764.
37. Krungkrai, S. R.; Yuthavong, Y. Trans. R. Soc. Trop. Med. Hyg. 1987, 81, 710-714.
38. Scott, M. D.; Mesnick, S. R.; Williams, R. A.; Chiu, D. T.-Y. J. Lab. Clin. Med. 1989, 114, 401-406.