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Synthesis and Pharmacological Screening of Novel meso ‐Substituted Porphyrin Analogs
Author(s) -
Fadda Ahmed A.,
ElMekawy Rasha E.,
ElShafei Ahmed I.,
Freeman Harold
Publication year - 2013
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.201200313
Subject(s) - chemistry , porphyrin , pyrrole , hemolysis , biological activity , oxidative phosphorylation , aldehyde , stereochemistry , aryl , medicinal chemistry , photochemistry , organic chemistry , biochemistry , in vitro , catalysis , alkyl , immunology , biology
A novel series of meso tetrakis[aryl]‐21 H ,23 H ‐porphyrin derivatives 2a – j was synthesized from the condensation of aldehyde derivatives 1a – j 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 bleomycin–iron complex. Compounds 2d , 2f , 2i , and 2j were proved to exhibit antioxidative activity.