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Iron(II)-Induced Degradation of Antimalarial β-Sulfonyl Endoperoxides. Evidence for the Generation of Potentially Cytotoxic Carbocations

2001; American Chemical Society; Volume: 66; Issue: 20 Linguagem: Inglês

10.1021/jo001265z

1520-6904

Alex M. Szpilman, Edward E. Korshin, Roland Hoos, Gary H. Posner, Mario D. Bachi,

Pharmacogenetics and Drug Metabolism

Reactions of antimalarial β-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 β-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.