Title
Synthesis and in vitro evaluation of tropane halogenated-derivatives against malaria, sleeping sickness, Chagas disease and leishmaniasis Synthesis and in vitro evaluation of tropane halogenated-derivatives against malaria, sleeping sickness, Chagas disease and leishmaniasis
Author
Faculty/Department
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences . Biomedical Sciences
Publication type
article
Publication
Subject
Chemistry
Pharmacology. Therapy
Source (journal)
Medicinal chemistry
Volume/pages
10(2014) :8 , p. 753-758
ISSN
1875-6638
ISI
000344525700001
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
A series of twelve analogs carrying fluoro, chloro, bromo and iodo halogens on the ortho, meta and para positions of a benzoyloxytropane skeleton were synthesized by a simple acylation of 8-methyl-8-aza-bicyclo[3.2.1]octan- 3α-ol by halogenobenzoyl chlorides. The compounds were evaluated in vitro against Plasmodium falciparum (P. f.), Trypanosoma brucei brucei (T. b. b.), Trypanosoma cruzi (T. c.) and Leishmania infantum (L. i.). This study shows that the presence of a halogenated atom and its position on the aromatic ring are important for in vitro activity. Compounds 4 (IC50 = 3.6 µM), 8 (IC50 = 6.7 µM), 5 (IC50 = 8.1 µM) and 7 (IC50 = 9.5 µM) were found the most active against P. f., whereas compounds 12 (IC50 = 5.1 µM), 11 (IC50 = 5.6 µM) and 9 (IC50 = 5.8 µM) exhibited the most pronounced activity against T. b. b. This series of compounds can be considered as non-toxic to the human cell line MRC-5.
E-info
https://repository.uantwerpen.be/docman/iruaauth/44e843/a1cac34ab44.pdf
Full text (open access)
https://repository.uantwerpen.be/docman/irua/9d2c11/9162.pdf
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