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The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone

✍ Scribed by Yuxiang Dong; Kevin J. McCullough; Sergio Wittlin; Jacques Chollet; Jonathan L. Vennerstrom

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 266 KB
Volume: 20
Category: Article
ISSN: 0960-894X
DOI: 10.1016/j.bmcl.2010.09.113

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✦ Synopsis

An unsaturated dispiro 1,2,4,5-tetraoxane formed by peroxidation of (+)-dihydrocarvone was converted into four structurally diverse derivatives. X-ray crystallographic analysis shows that the structures possess central tetraoxane rings with spiro-2,5-disubstituted cyclohexylidene substituents and 6-membered rings in classical chair conformations. As polarity in the tetraoxane series increased, in vitro potency against Plasmodium falciparum decreased.

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