A series of (Z)-2-benzylidenebenzofuran-3-(2H)-ones (aurones) bearing a variety of substituents on rings A and B were synthesized and evaluated for their antiparasitic activity against the intracellular amastigote form of Leishmania infantum and their cytotoxicity against human THP1-differentiated macrophages. In general, aurones bearing no substituents on ring A (compounds 4a–4f) exhibit higher toxicity than aurones with 4,6-dimethoxy substitution (compounds 4g–4l). Among the latter, two aurones possessing a 2′-methoxy or a 2′-methyl group (compounds 4i and 4j) exhibit potent antileishmanial activity (IC50 = 1.3 ± 0.1 μM and IC50 = 1.6 ± 0.2 μM, resp.), comparable to the activity of the reference drug Amphotericin B, whereas they present significantly lower cytotoxicity than Amphotericin B as deduced by the higher selectivity index.

The electrochemical behaviour of 13 chalcone analogues was systematically studied by means of cyclic voltammetry and chronoamperometry at a glassy carbon (GC), gold and platinum working electrodes using two different supporting electrolyte/solvent combinations. It was found that chalcone analogues can be easily oxidized at both GC and gold working electrodes, but not at a platinum electrode. Principal component analysis was further employed to reveal similarities/dissimilarities between oxidation potentials, chronoamperometric signals and ability of the compounds to scavenge the reactive oxygen species H 2 O 2 . The study reveals the inverse proportional relationship between the scavenging ability of H 2 O 2 , expressed as IC 50 , and chronoamperometric signal at 800 mV using gold as working electrode.