Synthesis of novel antibacterial metal free and metallophthalocyanines appending with four peripheral coumarin derivatives and their separation of structural isomers

Abstract

The preparation of novel metal-free phthalocyanines and metallophthalocyanine complexes 6 and 7 (MPcs, M = Co, Zn, Cu and Mn), with four peripheral 6-hydroxy-4-methylcoumarin and 6-hydroxycoumarin substituents, were prepared by cyclotetramerization of compounds 4 and 5 with the corresponding metal salts (Zn(OAc)22H2O, Co(OAc)24H2O, CuCl, Mn(OAc)24H2O) as a template for macrocycle formation in 2-(N,Ndimethylamino) ethanol whereby a mixture of four different structural isomers is obtained; two of these isomers, with C2 and Cs-symmetry are isolated by HPLC and characterized by FT-IR, UV-vis, elemental analyses, 1H NMR and 13C NMR spectroscopies. The electronic spectra exhibit a band of coumarin identity together with characteristic bands of the phthalocyanine core. The new compounds were screened for antibacterial activity. Most of them are more active against E. coli and S. aureus. © 2013 The Japan Institute of Heterocyclic Chemistry.