Article (Scientific journals)
Antiparasitic hybrids of Cinchona alkaloids and bile acids.
Leverrier, Aurelie; Bero, Joanne; Frederich, Michel et al.
2013In European Journal of Medicinal Chemistry, 66, p. 355-63
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Keywords :
Antiparasitic activity; Barton–Zard reaction; Bile acids; Cinchona alkaloids; Hybrids
Abstract :
[en] A series of 16 hybrids of Cinchona alkaloids and bile acids (4a-h, 5a-h) was prepared by means of a Barton-Zard decarboxylation reaction. Quinine, quinidine, cinchonine and cinchonidine were functionalized at position C-2 of the quinoline nucleus by radical attack of a norcholane substituent. The newly synthesized hybrids were evaluated in vitro for their antitrypanosomal, antileishmanial and antiplasmodial activities, along with their cytotoxicity against WI38, a normal human fibroblast cell line. Seven compounds (4d, 4f, 4h, 5b, 5d, 5f, 5h) showed promising trypanocidal activity with IC(5)(0) values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC(5)(0) </= 6 mug/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC(5)(0) values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6-15.7.
Disciplines :
Pharmacy, pharmacology & toxicology
Author, co-author :
Leverrier, Aurelie
Bero, Joanne
Frederich, Michel  ;  Université de Liège - ULiège > Département de pharmacie > Pharmacognosie
Quetin-Leclercq, Joelle
Palermo, Jorge
Language :
English
Title :
Antiparasitic hybrids of Cinchona alkaloids and bile acids.
Publication date :
2013
Journal title :
European Journal of Medicinal Chemistry
ISSN :
0223-5234
eISSN :
1768-3254
Publisher :
Elsevier, Netherlands
Volume :
66
Pages :
355-63
Peer reviewed :
Peer Reviewed verified by ORBi
Commentary :
Copyright (c) 2013 Elsevier Masson SAS. All rights reserved.
Available on ORBi :
since 02 December 2013

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