Synthesis of cynaropicrin-d(4)

Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated de...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2015-12, Vol.25 (23), p.5504-5507
Main Authors: Sato, Takuya, Hara, Shihori, Sato, Makiko, Ogawa, Keita, Adams, Michael, Usuki, Toyonobu
Format: Article
Language:English
Subjects:
Deuterium - chemistry
Lactones - chemical synthesis
Lactones - chemistry
Molecular Structure
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Trypanocidal Agents - chemical synthesis
Trypanocidal Agents - chemistry
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Summary:Cynaropicrin is a guaianolide sesquiterpene lactone, which has potent in vitro and in vivo inhibitory activity against Trypanosoma brucei, the protozoan parasite that causes human African trypanosomiasis (HAT; sleeping sickness). Herein, we describe the synthesis of cynaropicrin's deuterated derivative, cynaropicrin-d4, by the replacement of the side chain of natural cynaropicrin. The synthesized cynaropicrin-d4 could be employed as an internal standard for liquid chromatography-mass spectrometry (LC-MS) analysis, in the pharmacokinetic study of cynaropicrin. This could potentially advance the study of this therapeutic lead.
ISSN:1464-3405
DOI:10.1016/j.bmcl.2015.10.065