A series of 5-substitutedbenzylideneamino-2-butylbenzofuran-3-yl-4-methoxyphenyl methanones is synthesized and evaluated for antileishmanial and antioxidant activities. Compounds 4f (IC50 = 52.0 ± 0.09 µg/ml), 4h (IC50 = 56.0 ± 0.71 µg/ml) and 4l (IC50 = 59.3 ± 0.55 µg/ml) were shown significant antileishmanial when compared with standard sodium stibogluconate (IC50 = 490.0 ± 1.5 µg/ml). Antioxidant study revealed that compounds 4i (IC50 = 2.44 ± 0.47 µg/ml) and 4l (IC50 = 3.69 ± 0.44 µg/ml) have shown potent comparable activity when compared with standard ascorbic acid (IC50 = 3.31 ± 0.34 µg/ml). Molecular docking study was carried out which replicating results of biological activity in case of initial hits 4f and 4h suggesting that these compounds have a potential to become lead molecules in drug discovery process. In silico ADME study was performed for predicting pharmacokinetic profile of the synthesised antileishmanial agents and expressed good oral drug like behaviour.