Investigations on the antiplasmodial activity of ferrocenyl chalcones

Abstract

A series of ferrocenyl chalcones were synthesized and their antiplasmodial activities were evaluated. A structure-activity relationship study was carried out with multivariate tools and the mode of antiplasmodial action was also investigated.About 1/3rd of the ferrocenyl chalcones showed antiplasmodial activity with IC50 values less than 20 i?-M. The most active compounds were 1-(3a??-pyridinyl)-3-ferrocenyl-2-propen-1-one (6) (IC50 4.6 i?-M) and 1-ferrocenyl-3-(4a??-nitrophenyl)-2-propen-1-one (28) (IC50 5.1 i?-M).In the QSAR study, oxidizability of ferrocene and the polarity of carbonyl linkage were identified as important parameters for antiplasmodial activity.The investigations on the scavenging of ABTS radical cation and free radical generation showed that ferrocenyl chalcones could generate free radicals rapidly but without a robust correlation with their antiplasmodial activity.In conclusion, the study has shown that ferrocenyl chalcones demonstrated antiplasmodial activity in vitro. Ferrocene was found to markedly affect the physicochemical properties of ferrocenyl chalcones and to influence antiplasmodial activity of these compounds.