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Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin

Authors
Bray, Dorothy H.
Warhurst, David C.
Milhous, Wilbur K.
Published in Helvetica Chimica Acta. 1993, vol. 76, no. 8, p. 2775-2788
Abstract Two sets of tricyclic 1,2,4-trioxanes containing the ABC (10, 11) and ACD ring portions (21, 22, 32, 33, 37, and 38) of artemisinin (1) were synthesized by successive photo-oxygenation of appropriate enol-ether precursors to 1,2-dioxanes and inter- and intramolecular reaction with a carbonyl compound or oxo-substituted side-chain. The structures of 10, 21, and 22 were determined by X-ray analysis. The anti-malarial activity of all trioxanes, except 37 and 38, was evaluated in vitro against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum parasites. Trioxanes 11 and 21 were as active as artemisinin (1). It was found that neither the lactone function nor rings B and D of 1 were essential for activity. A possible pharmacophore for artemisinin-like activity, which embodies a spirocyclopentane group attached to C(3) of 1,2,4-trioxane, was proposed.
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Other version: http://doi.wiley.com/10.1002/hlca.19930760804
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JEFFORD, Charles et al. Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin. In: Helvetica Chimica Acta, 1993, vol. 76, n° 8, p. 2775-2788. https://archive-ouverte.unige.ch/unige:84783

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