Synthesis of metallocomplexes of water soluble bisquinolinylporhyrins as potential antimicrobial agents

Abstract

At present, extensive research is being carried out on the phenomenon of resistance of microbes to antibiotics, including the newest of them. Among the most promising drug candidates for treatment such superbugs is derivatives of 5,15-disubstituted water-soluble porphyrins developed and patented by Destiny Pharma, UK. Here, we continued of our investigation of quinolinylporphyrins and report about synthesis of 5,15-di(n-propyl)-10,20-di(3-quinolinyl)porphyrine and its isomer - 5,10-di(n-propyl)-15,20-di(3-quinolinyl)porphyrine and their complexes with Fe and Mn. The porphyrins was obtained by mixed aldehydes condensation of mixture quinoline-3-carbaldehyde and n-butyraldehyde with pyrrole in propionic acid with small amount propionic anhydride. Above mentioned porphyrins was separated and purified by column chromatography on silica gel and their Fe and Mn complexes was synthesized in refluxing DMF by treatment respectively FeCl3 and Mn(CH3CO2)2. Water-soluble form of the metalloporphyrines was obtained by quaternization of nitrogen atom of quinolinyl substituents by methyl-paratoluenesulfonate for further investigation their antimicrobial properties.