edoc

Natural product derived antiprotozoal agents : synthesis, biological evaluation, and structure-activity relationships of novel chromene and chromane derivatives

Harel, Dipak and Schepmann, Dirk and Prinz, Helge and Brun, Reto and Schmidt, Thomas J. and Wünsch, Bernhard. (2013) Natural product derived antiprotozoal agents : synthesis, biological evaluation, and structure-activity relationships of novel chromene and chromane derivatives. Journal of medicinal chemistry, 56 (18). pp. 7442-7448.

Full text not available from this repository.

Official URL: http://edoc.unibas.ch/dok/A6194655

Downloads: Statistics Overview

Abstract

Various natural products with the chromane and chromene scaffold exhibit high antiprotozoal activity. The natural product encecalin (7) served as key intermediate for the synthesis of different ethers 9, amides 11, and amines 12. The chromane analogues 14 and the phenols 15 were obtained by reductive amination of ketones 13 and 6, respectively. Angelate 3, ethers 9, and amides 11 did not show considerable antiprotozoal activity. However, the chromene and chromane derived amines 12, 14, and 15 revealed promising antiprotozoal activity and represent novel lead compounds. Whereas benzylamine 12a and α-methylbenzylamine 12g were active against P. falciparum with IC50 values in the range of chloroquine, the analogous phenols 15a and 15b were unexpectedly 10- to 25-fold more potent than chloroquine with selectivity indexes of 6760 and 1818, respectively. The phenylbutylamine 14d based on the chromane scaffold has promising activity against T. brucei rhodesiense and L. donovani.
Faculties and Departments: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)
UniBasel Contributors:Brun, Reto
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:American Chemical Society
ISSN:0022-2623
Note:Publication type according to Uni Basel Research Database: Journal article
Related URLs:
Identification Number:
Last Modified:13 Sep 2018 14:31
Deposited On:31 Jan 2014 09:49

Repository Staff Only: item control page