Antitrypanosomal structure–activity-relationship study of synthetic cynaropicrin derivatives

Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2014-02, Vol.24 (3), p.794-798
Main Authors: Usuki, Toyonobu, Sato, Makiko, Hara, Shihori, Yoshimoto, Yukiko, Kondo, Ryosuke, Zimmermann, Stefanie, Kaiser, Marcel, Brun, Reto, Hamburger, Matthias, Adams, Michael
Format: Article
Language:English
Subjects:
Cynaropicrin
Derivatization
Guaianolide
Inhibitory Concentration 50
Lactones - chemical synthesis
Lactones - chemistry
Lactones - pharmacology
Molecular Structure
SAR
Sesquiterpenes - chemical synthesis
Sesquiterpenes - chemistry
Sesquiterpenes - pharmacology
Structure-Activity Relationship
Trypanocidal Agents - chemical synthesis
Trypanocidal Agents - chemistry
Trypanocidal Agents - pharmacology
Trypanosoma brucei
Trypanosoma brucei brucei - drug effects
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Summary:Cynaropicrin is a guaianolide sesquiterpene lactone with a 5-7-5 tricyclic skeleton, four exo-olefins, and two hydroxyl groups. Recently, it was found that the compound is a potent in vitro and in vivo inhibitor of the protozoan parasite Trypanosoma brucei, which causes human African trypanosomiasis (HAT; sleeping sickness). In this Letter, chemical derivatization of cynaropicrin and the structure–activity-relationship (SAR) study against T. brucei is described.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2013.12.099