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Design, synthesis and anti-plasmodial evaluation in vitro of new 4-aminoquinoline isatin derivatives.

Abstract：

:A new class of 4-aminoquinoline derivatives based on the natural product isatin scaffold were designed and synthesized for biological evaluation against three strains of the malaria parasite Plasmodium falciparum. These derivatives showed anti-plasmodial IC(50) values in the ranges of 1.3-0.079 and 2.0-0.050muM against a chloroquine-sensitive (D10) and two resistant (K1 and W2) strains of P. falciparum, respectively. In order to determine potential targets for this class of compounds in P. falciparum, selected compounds were also tested against the parasitic cysteine protease falcipain-2. In terms of further development of this class of isatin derivatives, two of the compounds based on a flexible alkyl chain linker and a thiosemicarbazone moiety warrant further investigation as potential anti-plasmodial leads. These two derivatives showed good in vitro activity against K1 and W2 with IC(50) values of 51 and 54nM, respectively, while retaining potency against the D10 strain with IC(50) values of 79 and 95nM, respectively. Generally speaking, the inhibitory potency of all compounds in the series against the parasites did not strongly correlate with inhibitory potency against falcipain-2 for selected compounds tested, which at best was weak to moderate, suggesting other mechanisms of inhibition may also be involved or compounds may be selectively taken up by Plasmodium falciparum.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Chiyanzu I,Clarkson C,Smith PJ,Lehman J,Gut J,Rosenthal PJ,Chibale K

doi

10.1016/j.bmc.2005.02.037

subject

Has Abstract

pub_date

2005-05-02 00:00:00

pages

3249-61

issue

9

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(05)00150-1

journal_volume

13

pub_type

杂志文章

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