Antimalarial endoperoxides that are potent and easily synthesized

Journal of Pharmacy and Pharmacology

Volumn 49, Issue SUPPL. 2, 1997, Pages 55-57

  Posner, Gary H ^a  

^a JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIMALARIAL AGENT; ARTEMISININ; ATOVAQUONE; ENDOPEROXIDE;

ANTIMALARIAL ACTIVITY; ARTICLE; DRUG METABOLISM; DRUG STRUCTURE; DRUG SYNTHESIS;

EID: 0030956443     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.2042-7158.1997.tb06161.x     Document Type: Article

References (14)

1. Avery, M. A., Fan, P., Karle, J. M., Bank, J. D., Miller, R., Goins, D. K. (1996) Structure-activity relationships of the antimalarial agent artemisinin. 3. Total synthesis of (+)-13-carbaartemisinin and related tetra- and tricyclic structures. J. Med. Chem. 39: 1885
2. Cumming, J. N., Ploypradith, P., Posner, G. H. (1996) Antimalarial activity of artemsinin (qinghaosu) and related trioxanes: mechanism(s) of action. Adv. Pharmacol. 37: 253-296
3. Fishwick, J., McLean, W. G., Edwards, G., Ward, S. A. (1995) The toxicity of artemisinin and related compounds on neuronal and glial cells in culture. Chem. Biol. Interact. 96: 263-271
4. Goldsmith, R. S. (1992) Antiprotozoal drugs, In: Katzung, B. G. (ed.) Basic and Clinical Pharmacology. Appleton & Lange, Norwalk, CT, p. 735
5. Meshnick, S. R., Taylor, T. E., Kamchonwongpaisan, S. (1996) Artemisinin and the antimalarial endoperoxides: from herbal remedy to targeted chemotherapy. Microbiol. Rev. 60: 301-315
6. Ortiz de Montellano, P. R. (1985) Chapter 5. In: Anders, M. W. (ed.) Bioactivation of Foreign Compounds. Academic Press, New York, p. 121-155
7. Ou-Yang, K., Krug, E. C., Marr, J. J., Berens, R. L. (1990) Inhibition of growth of Toxoplasma gondii by qinghaosu and derivatives. Antimicrob. Agents Chemother. 34: 1961-1965
8. Peters, W., Robinson, B. L., Tovey, G., Rossier, J. C., Jefford, C. W. (1993) The chemotherapy of rodent malaria. L. The activities of some synthetic 1,2,4-trioxanes against chloroquine-sensitive and chloroquine-resistant parasites. Part 3: observations on 'fenozan-50F', a difluorinated 3,3′-spirocyclopentane 1,2,4-trioxane. Ann. Trop. Med. Parasitol. 87: 111-123
9. Posner, G. H., Oh, C. H., Wang, D., Gerena, L., Milhous, W. K., Meshnick, S. R., Asawamahasakda, W. (1994) Mechanism-based design, synthesis, and in vitro antimalarial testing of new 4-methylated trioxanes structurally related to artemisinin: the importance of a carbon-centered radical for antimalarial activity. J. Med. Chem. 37: 1256-1258
10. Posner, G. H., Cumming, J. N., Ploypradith, P., Oh, C. H. (1995) Evidence for Fe(IV) = O in the molecular mechanism of action of the trioxane antimalarial artemisinin. J. Am. Chem. Soc. 117: 5885-5886
11. Posner, G. H., Wang, D. W., Gonzlez, L., Tao, X., Cumming, J. N., Klinedinst, D., Shapiro, T. A. (1996a) Mechanism-based design of simple, symmetrical, easily prepared, potent antimalarial endoperoxides. Tetrahedron Lett. 37: 815-818
12. Posner, G. H., Tao, X., Cumming, J. N., Klinedinst, D., Shapiro, T. A. (1996b) Antimalarially potent, easily prepared, fluorinated endoperoxides. Tetrahedron Lett. 37: 7225-7228
13. Sweeney, T. R. (1981) The present status of malaria chemotherapy: mefloquine, a novel antimalarial. Med. Res. Rev. 1: 281-301
14. Zhou, W. S., Xu, X. X. (1994) Total synthesis of the antimalarial sesquiterpene peroxide qinghaosu and yingzhaosu A. Acc. Chem. Res. 27: 211-216