Antitrypanosomal structure-activity-relationship study of synthetic cynaropicrin derivatives

Bioorg Med Chem Lett. 2014 Feb 1;24(3):794-8. doi: 10.1016/j.bmcl.2013.12.099.

Toyonobu Usuki ¹, Makiko Sato ², Shihori Hara ², Yukiko Yoshimoto ², Ryosuke Kondo ², Stefanie Zimmermann ³, Marcel Kaiser ⁴, Reto Brun ⁴, Matthias Hamburger ⁵, Michael Adams ⁵

Affiliations

1 Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan. Electronic address: t-usuki@sophia.ac.jp.
2 Department of Materials and Life Sciences, Faculty of Science and Technology, Sophia University, 7-1 Kioicho, Chiyoda-ku, Tokyo 102-8554, Japan.
3 Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland; Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Socinstrasse 57, CH-4002 Basel, Switzerland.
4 Department of Medical Parasitology and Infection Biology, Swiss Tropical and Public Health Institute, Socinstrasse 57, CH-4002 Basel, Switzerland.
5 Division of Pharmaceutical Biology, Department of Pharmaceutical Sciences, University of Basel, Klingelbergstrasse 50, CH-4056 Basel, Switzerland.

PMID: 24433861 DOI: 10.1016/j.bmcl.2013.12.099

Abstract

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.

Keywords

Cynaropicrin; Derivatization; Guaianolide; SAR; Trypanosoma brucei.

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