Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.

Synthesis of (+)-7,20-Diisocyanoadociane and Liver-Stage Antiplasmodial Activity of the Isocyanoterpene Class.
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DOI:
10.1021/jacs.6b03899
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发表时间:
2016-06-15
影响因子:
15
通讯作者:
Shenvi RA
Shenvi RA
中科院分区:
化学1区
文献类型:
--
作者:
Lu HH;Pronin SV;Antonova-Koch Y;Meister S;Winzeler EA;Shenvi RA

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7,20-Diisocyanoadociane 是一种稀有的海洋代谢物,具有有效的抗疟活性,是通过简单的构建模块(17 个线性步骤)通过 13 个步骤合成为单一对映体。化学合成能够鉴定 ICT 抗肝期寄生虫的抗疟原虫活性,这表明血红素解毒并不完全是此类药物的作用机制。
7,20-Diisocyanoadociane, a scarce marine metabolite with potent antimalarial activity, was synthesized as a single enantiomer in 13 steps from simple building blocks (17 linear steps). Chemical synthesis enabled identification of ICT antiplasmodial activity against liver-stage parasites, which suggested heme detoxification does not exclusively underlie the mechanism of action of this class.
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