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Title

Synthesis, Structure, and Antimalarial Activity of Tricyclic 1,2,4-Trioxanes Related to Artemisinin
Authors
Jefford, Charles
Velarde Mendoza, Javier Antonio
Bernardinelli, Gérald Hugues
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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Article (Published version) (831 Kb) - document accessible for UNIGE members only Limited access to UNIGE
Structures
Faculté des sciences / Section de chimie et biochimie / Département de chimie organique
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(ISO format) 		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. doi: 10.1002/hlca.19930760804 https://archive-ouverte.unige.ch/unige:84783

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Deposited on : 2016-06-28

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