Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 67, Issue 3, Pages 609-619Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo010688d
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The reactivity of 1,2,4-trioxane molecules 2-5, structurally related to the antimalarial drug artemisinin, with a heme model, manganese(II) tetraphenylporphyrin, is reported. With the pharmacologically active drugs 2-4, covalent adducts were obtained by addition of a drug-derived radical onto the porphyrin macrocycle, whereas no reaction was obtained with the nonactive compound 5. This confirms that alkylation is probably one of the key factors of the pharmacological activity of endoperoxide-based antimalarial drugs.
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