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Iron(II)-induced degradation of antimalarial β-sulfonyl endoperoxides.: Evidence for the generation of potentially cytotoxic carbocations

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JOURNAL OF ORGANIC CHEMISTRY
卷 66, 期 20, 页码 6531-6540

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AMER CHEMICAL SOC
DOI: 10.1021/jo001265z

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Reactions of antimalarial P-sulfonyl endoperoxides 9 and 10, which, like yingzhaosu A (2), derive from the 2,3 -dioxabicyclo[3.3.1]nonane system 3, with iron(II) salts were studied. Product analysis of the iron(II)-induced degradations provided evidence for the intermediacy of carbon-centered cyclohexyl, radicals 20 and 31 and their possible oxidation to the corresponding carbocations 21 and 32. It is conceivable that the antimalarial activity of beta -sulfonyl endoperoxides of type 5 may derive from alkylation of vital intraparasitic. biomolecules by free radicals and/or carbocations, generated within the malaria parasite through a similar iron(II)-induced degradation process.

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