Synthesis of cynaropicrin-d(4).

Abstract

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.

• Authors: Takuya Sato, Shihori Hara, Makiko Sato, Keita Ogawa, Michael Adams, Toyonobu Usuki
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 25 Issue 23 Pg. 5504-7 (Dec 01 2015) ISSN: 1464-3405 [Electronic] England
• PMID: 26520660 (Publication Type: Journal Article)
• Copyright: Copyright © 2015 Elsevier Ltd. All rights reserved.

Chemical References

• Lactones
• Sesquiterpenes
• Trypanocidal Agents
• cynaropicrin-d
• Deuterium
• cynaropicrin

Topics

• Deuterium (chemistry)
• Lactones (chemical synthesis, chemistry)
• Molecular Structure
• Sesquiterpenes (chemical synthesis, chemistry)
• Trypanocidal Agents (chemical synthesis, chemistry)