Iron(II)-Induced Degradation of Antimalarial β-Sulfonyl Endoperoxides. Evidence for the Generation of Potentially Cytotoxic Carbocations
| Autor: | Gary H. Posner, Bachi, Roland Hoos, Edward E. Korshin, Alex M. Szpilman |
|---|---|
| Rok vydání: | 2001 |
| Předmět: |
Sulfonyl
chemistry.chemical_classification Free Radicals Iron Organic Chemistry Yingzhaosu A Carbocation Sulfinic Acids Combinatorial chemistry Peroxides Antimalarials Product analysis chemistry.chemical_compound chemistry Cytotoxic T cell Degradation (geology) Prodrugs Nonane Beta (finance) Oxidation-Reduction |
| Zdroj: | The Journal of Organic Chemistry. 66:6531-6540 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/jo001265z |
| Popis: | Reactions of antimalarial beta-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. |
| Databáze: | OpenAIRE |
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