4.8 Article

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

Journal

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 138, Issue 23, Pages 7268-7271

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/jacs.6b03899

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Funding

  1. NIH [GM105766]
  2. Eli Lilly
  3. Novartis
  4. Bristol-Myers Squibb
  5. Amgen
  6. Boehringer-Ingelheim
  7. Sloan Foundation
  8. Baxter Foundation

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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.

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