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Antiparasitic hybrids of Cinchona alkaloids and bile acids.

Abstract：

: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 IC₅₀ values in the same range as the commercial drug suramine. Moreover all the 16 hybrids showed antiplasmodial activity (IC₅₀ ≤ 6 μg/ml), particularly those containing a nor-chenodeoxycholane moiety (4b, 4d, 4f, 4h, 5b, 5d, 5f, 5h) with IC₅₀ values comparable to those of the natural alkaloids, and selectivity indices in the range of 5.6-15.7.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Leverrier A,Bero J,Frédérich M,Quetin-Leclercq J,Palermo J

doi

10.1016/j.ejmech.2013.06.004

subject

Has Abstract

pub_date

2013-08-01 00:00:00

pages

355-63

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(13)00369-3

journal_volume

66

pub_type

杂志文章

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