Synthesis, characterization and bioactive evaluation of copper(II) 5,10,15,20-tetrakis[alpha,alpha,alpha,alpha-2-(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethyl phenol)phenyl] porphyrin: a picket-fence porphyrin

Abstract

We are interested in constructing deeper small cavities by adding more bulky substituents at the ortho-phenyl positions of tetrakis(o-aminophenyl)porphyrin. The synthesis of picket-fence porphyrin is initiated by the preparation of the tetrakis(o-nitrophenyl)porphyrin followed by the nitro to amino reduction and subsequent condensation with Schiff base ligand to form imine linkages of porphyrin complexes. The synthesis and characterization of a new series of picket-fence porphyrins and their copper complexes are described. 5,10,15,20-Tetrakis[alpha,alpha,alpha,alpha-2-(2,6-bis(4-methyl piperazine-1-yl-methyl)-4-iminomethyl phenol)phenyl] porphyrin can be synthesized from 2,6-bis[4-methylpiperazin-1-yl-methyl]-4-formylphenol (L) and 5,10,15,20-tetra[alpha,alpha,alpha,alpha-o-nitropheny1]-porphyrin. 5,10,15,20-Tetra[alpha,alpha,alpha,alpha-o-aminopheny1]-porphyrin was obtained by the reduction of 5,10,15,20-tetra[alpha,alpha,alpha,alpha-o-nitropheny1]-porphyrin. The spectral, electrochemical, antibacterial, antifungal and cytotoxicity properties of all the picket-fence porphyrin complexes were characterized and studied.