De Mieri, M. and Kaiser, M. and Brun, R. and Thormann, U. and Imanidis, G. and Hamburger, M.. (2015) Anti-trypanosomal cadinanes synthesized by transannular cyclization of the natural sesquiterpene lactone nobilin. Bioorganic & medicinal chemistry, 23 (7). pp. 1521-1529.
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Official URL: http://edoc.unibas.ch/dok/A6357896
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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.
| Faculties and Departments: | 05 Faculty of Science > Departement Pharmazeutische Wissenschaften > Ehemalige Einheiten Pharmazie > Pharmazeutische Biologie (Hamburger) 09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) 09 Associated Institutions > Swiss Tropical and Public Health Institute (Swiss TPH) > Department of Medical Parasitology and Infection Biology (MPI) > Parasite Chemotherapy (Mäser) |
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| UniBasel Contributors: | Imanidis, Georgios and Brun, Reto and Hamburger, Matthias and Kaiser, Marcel and de Mieri, Maria |
| Item Type: | Article, refereed |
| Article Subtype: | Research Article |
| Publisher: | Pergamon |
| ISSN: | 0968-0896 |
| Note: | Publication type according to Uni Basel Research Database: Journal article |
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| Identification Number: |
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| Last Modified: | 08 Dec 2017 14:02 |
| Deposited On: | 10 Apr 2015 09:13 |
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