Synthesis and Pharmacological Screening of Novel meso-Substituted Porphyrin Analogs

A novel series of mesotetrakis[aryl]-21H,23H-porphyrin derivatives 2aj was synthesized from the condensation of aldehyde derivatives 1aj with pyrrole in the presence of p-toluenesulfonic acid. The synthesized porphyrins were considered as a model to study the free radical-induced damage of biological membranes and the protective effects of these porphyrins. It was found that these compounds effectively inhibit the free radical-induced oxidative hemolysis of red blood cells. Compounds 2c and 2d which bear a sulfur atom, a nitro group, and a chlorine atom exhibited markedly higher antihemolysis activity than the other analogous. Compounds 2a, 2c, 2d, and 2j showed the highest protection activity against DNA damage induced by the bleomyciniron complex. Compounds 2d, 2f, 2i, and 2j were proved to exhibit antioxidative activity.