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

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 isocyanoterpene antiplasmodial activity against liver-stage parasites,...

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Veröffentlicht in:Journal of the American Chemical Society 2016-06, Vol.138 (23), p.7268-7271
Hauptverfasser: Lu, Hai-Hua, Pronin, Sergey V, Antonova-Koch, Yevgeniya, Meister, Stephan, Winzeler, Elizabeth A, Shenvi, Ryan A
Format: Artikel
Sprache:eng
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Zusammenfassung: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 isocyanoterpene antiplasmodial activity against liver-stage parasites, which suggested that inhibition of heme detoxification does not exclusively underlie the mechanism of action of this class.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.6b03899