The design, the synthesis and the study of the antioxidant and vasodilating properties of new hybrids obtained by linking different antioxidant phenolic moieties to the furoxan substructure present in CHF2363, which can release nitric oxide, are described. All the final NO-phenols were endowed with both antioxidant and vasodilating properties. The antioxidant activities were assessed on the ferrous salt/ascorbate induced autooxidation of lipids present in microsomial membranes of rat hepatocytes. The vasodilating activities were assessed on rat aorta strips precontracted with phenylephrine, in the presence and absence of ODQ. The antioxidant potencies (IC 50 values) and the vasodilating potencies (EC 50 values) were widely modulated into the series. Further in vivo studies should clarify whether these products may become preclinical candidates for the treatment of atherosclerosis and related disorders.