title: 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.
authors.affiliation: Department of Inorganic Chemistry, University of Madras, Chennai, Tamil Nadu, India.
authors.forename: K
authors.initials: K
authors.lastname: Rajesh
authors.forename: A Kalilur
authors.initials: AK
authors.lastname: Rahiman
authors.forename: K Shanmuga
authors.initials: KS
authors.lastname: Bharathi
authors.forename: S
authors.initials: S
authors.lastname: Sreedaran
authors.forename: V
authors.initials: V
authors.lastname: Gangadevi
authors.forename: V
authors.initials: V
authors.lastname: Narayanan
mesh_terms: D000890:Anti-Infective Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D001234:Aspergillus niger / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D045744:Cell Line, Tumor / Q000187:drug effects / Q000648:ultrastructure; D056831:Coordination Complexes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D052978:Disk Diffusion Antimicrobial Tests; D004353:Drug Evaluation, Preclinical; D004354:Drug Screening Assays, Antitumor; D055664:Electrochemical Techniques; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006801:Humans; D008665:Metalloporphyrins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010879:Piperazines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013050:Spectrometry, Fluorescence; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013211:Staphylococcus aureus / Q000187:drug effects
chemical_list: D000890:Anti-Infective Agents; D056831:Coordination Complexes; D008665:Metalloporphyrins; D010879:Piperazines; C554189:copper(II) 5,10,15,20-tetrakis(alpha,alpha,alpha,alpha-2-(2,6-bis(4-methylpiperazine-1-ylmethyl)-4-iminomethylphenol)phenyl)porphyrin