New NO-donors with antithrombotic activities and vasodilating activities, III: 3,4-disubstituted N-nitroso-5-sydnone imines

Article abstract of DOI:10.1002/ardp.19933261204

38 title compounds have been synthesized. They bear a wide variety in substituents including alkyl-, aryl-, arylalkyl-, and styryl groups. The antiplatelet activities elucidated in the Born-test with collagen cover more than two orders of magnitude (IC₅₀ = 0.3-45 μmol/L). These effects depend on the presence of the N-NO-group. This is shown by comparison with the corresponding sydnone imines, sydnone cyanimines, and sydnones. The most suitable substituents were phenylethyl, styryl, and hexyl at either position of the molecule. Seven compounds, most of them styryl derivatives, have IC₅₀ values below 1 μmol/L. It is suggested that the differences in activity are connected with the ability of the compounds to bind to the platelet membrane.