A series of Schiff bases have been synthesized from dicarbaldehyde of benzocoumarin, in which the reactions were regioselective and the products existed in the keto-enamine form, in which the aromaticity of the relevant ring was disrupted. The compounds were evaluated in vitro for their antioxidant and in vivo for their antidyslipidemic activity for the first time. Compounds 3 and 7 possess significant lipid lowering and antioxidant activity.