The biomimetic iron-mediated degradation of ARTEFLENE (cas 123407-36-3) (Ro-42-1611),an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity

Add time:07/20/2019    Source:sciencedirect.com

ARTEFLENE (cas 123407-36-3) 4 reacts with FeCl2.4H2O in acetonitrile or with hemin / N-acetylcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with ZnAcOH, a model of NADH dehydrogenase, results in the formation of the diol 5 in 80% yield. The formation of the enone 6 indicates that arteflene fragments to a non-stabilised carbon-centred radical. This radical intermediate is proposed to mediate the potent antimalarial activity of 4.

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