Various benzylideneamino-5H-thiochromeno[2,3-b]pyridin-5-one derivatives were synthesized by the reaction of 7-amino-5H-[1] benzothiopyrano[2,3-b]pyridin-5-one and different benzaldehydes. Their structures were confirmed on the basis of Mass, 1H NMR, IR spectra and elemental analysis. These compounds were screened for their antioxidant and antibacterial properties. The results reveal that some compounds have pronounced antioxidant and antibacterial activities.