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Probing the aurone scaffold against Plasmodium falciparum: design, synthesis and antimalarial activity.

Abstract：

:A library comprising 44 diversely substituted aurones derivatives was synthesized by straightforward aldol condensation reactions of benzofuranones and the appropriately substituted benzaldehydes. Microwave enhanced synthesis using palladium catalyzed protocols was introduced as a powerful strategy for extending the chemical space around the aurone scaffold. Additionally, Mannich-base derivatives, containing a 7-aminomethyl-6-hydroxy substitution pattern at ring A, were also prepared. Screening against the chloroquine resistant Plasmodium falciparum W2 strain identified novel aurones with IC50 values in the low micromolar range. The most potent compounds contained a basic moiety, with the ability to accumulate in acidic digestive vacuole of the malaria parasite. However, none of those aurones revealed significant activity against hemozoin formation and falcipain-2, two validated targets expressed during the blood stage of P. falciparum infection and functional in digestive vacuole of the parasite. Overall, this study highlight (i) the usefulness of aurones as platforms for synthetic procedures using palladium catalyzed protocols to rapidly deliver lead compounds for further optimization and (ii) the potential of novel aurone derivatives as promising antimalarial compounds.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Carrasco MP,Newton AS,Gonçalves L,Góis A,Machado M,Gut J,Nogueira F,Hänscheid T,Guedes RC,dos Santos DJ,Rosenthal PJ,Moreira R

doi

10.1016/j.ejmech.2014.04.076

subject

Has Abstract

pub_date

2014-06-10 00:00:00

pages

523-34

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(14)00405-X

journal_volume

80

pub_type

杂志文章

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