| Literature DB >> 25740635 |
Maria De Mieri1, Marcel Kaiser2, Reto Brun2, Ursula Thormann3, Georgios Imanidis3, Matthias Hamburger4.
Abstract
Acid-catalyzed transannular cyclization of the germacrene-type sesquiterpene lactone nobilin 1 was investigated with the aim of obtaining new anti-trypanosomal cadinane derivatives. The reaction was regiospecific in all tested reaction conditions. Compounds were fully characterized by spectroscopic and computational methods, and the anti-trypanosomal activity was evaluated and compared to nobilin (IC50 3.19±1.69μM). The tricyclic derivative 11 showed most potent in vitro activity against Trypanosoma brucei rhodesiense bloodstream forms (IC50 0.46±0.01μM). Acid-catalyzed transannular cyclization of natural cyclodecadienes is an efficient strategy to generate new natural product derivatives with anti-protozoal activity.Entities:
Keywords: Anti-trypanosomal activity; Heliangolide; Sesquiterpene lactones; Transannular cyclization
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Year: 2015 PMID： 25740635 DOI： 10.1016/j.bmc.2015.02.005
Source DB: PubMed Journal: Bioorg Med Chem ISSN： 0968-0896 Impact factor: 3.641