New syntheses and potential antimalarial activities of new ‘retinoid-like chalcones’

A series of ‘retinoid-like chalcones’ and diverse derivatives relative to licochalcone A were synthesized from a new enaminone synthon. These syntheses occurred via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agents. The 4-hydroxy-chalcone-like (compound 6a, derived from β-ionone) exhibits a good and reproducible inhibitory effect on the in vitro culture of Plasmodium falciparum, with an IC 50 lower than 10 μM for inhibition of 3H-hypoxanthine uptake by parasites (respectively, 4.93 and 8.47 μM for strains K1 and Thaï).

Graphical abstractA series of ‘retinoid-like chalcones’ were synthesized from a new enaminone synthon, via a new aromatic annelation. These new derivatives have been tested in vitro as potential antimalarial agentsFigure optionsDownload full-size imageDownload as PowerPoint slide