The structure and antimalarial activity of dispiro-1,2,4,5-tetraoxanes derived from (+)-dihydrocarvone
Yuxiang Dong1, Kevin J McCullough, Sergio Wittlin
1University of Nebraska Medical Center, College of Pharmacy, 986025 Nebraska Medical Center, Omaha, NE, USA.
Abstract:
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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