The biomimetic iron-mediated degradation of arteflene (Ro-42-1611), an endoperoxide antimalarial: Implications for the mechanism of antimalarial activity

被引：44

作者：

ONeill, PM ^{[1
]}

Bishop, LP ^{[1
]}

Searle, NL ^{[1
]}

Maggs, JL ^{[1
]}

Ward, SA ^{[1
]}

Bray, PG ^{[1
]}

Storr, RC ^{[1
]}

Park, BK ^{[1
]}

机构：

[1] UNIV LIVERPOOL,DEPT CHEM,LIVERPOOL L69 3BX,MERSEYSIDE,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 24期

关键词：

D O I：

10.1016/S0040-4039(97)00874-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Arteflene 4 reacts with FeCl2 . 4H(2)O in acetonitrile or with hemin / N-acetytcysteine (heme Fe(II)) in acetonitrile to produce the diol 5 and the enone 6. Treatment of arteflene with Zn/AcOH, 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. (C) 1997 Elsevier Science Ltd.

引用

页码：4263 / 4266

页数：4

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