Synthesis and antimalarial activity of (+)-deoxoartemisinin

(+)-Deoxoartemisinin (2), a new and more active antimalarial agent, was successfully prepared from artemisinin in one step using NaBH4 and BF3.Et2O in THF. (-)-Deoxodeoxyartemisinin (5), a potential metabolite of deoxoartemisinin, was also prepared either from 2 or from artemisinic acid. 2 shows 8-f...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1990-05, Vol.33 (5), p.1516-1518
Main Authors: Jung, Mankil, Li, Xun, Bustos, Daniel A, ElSohly, Hala N, McChesney, James D, Milhous, Wilbur K
Format: Article
Language:English
Subjects:
Animals
Antimalarials - chemical synthesis
Artemisinins
Chemical Phenomena
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives
Malaria - drug therapy
Mice
Organic chemistry
Preparations and properties
Sesquiterpenes - chemical synthesis
Sesquiterpenes - pharmacology
Sesquiterpenes - therapeutic use
Stereoisomerism
Structure-Activity Relationship
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Summary:(+)-Deoxoartemisinin (2), a new and more active antimalarial agent, was successfully prepared from artemisinin in one step using NaBH4 and BF3.Et2O in THF. (-)-Deoxodeoxyartemisinin (5), a potential metabolite of deoxoartemisinin, was also prepared either from 2 or from artemisinic acid. 2 shows 8-fold increased antimalarial activity in vitro against chloroquine-resistant malaria as compared to artemisinin (1). Compound 2 possesses superior in vivo antimalarial activity to 1.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00167a036