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Paper | Regular issue | Vol 87, No. 11, 2013, pp.2283-2297
Published online, 25th September, 2013
DOI: 10.3987/COM-13-12816
■ SYNTHESIS OF NOVEL ANTIBACTERIAL METAL FREE AND METALLOPHTHALOCYANINES APPENDING WITH FOUR PERIPHERAL COUMARIN DERIVATIVES AND THEIR SEPARATION OF STRUCTURAL ISOMERS

Rawdha Medyouni, Naceur Hamdi,* Anis Ben Hsouna, Abdullah Sulaiman Al-Ayed, Hussain Ali Soleiman, Fethi Zaghrouba, and Christian Bruneau

*Chemistry Department, College of Science, Qassim University, P.O.Box 8000, Saudi Arabia

Abstract

The preparation of novel metal-free phthalocyanine 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 and characterized by cyclotetramerization of compounds 4 and 5 with the corresponding metal salts (Zn(OAc)2·2H2O, Co(OAc)2·4H2O, CuCl, Mn(OAc)2·4H2O) as a template for macrocycle formation in 2-(N,N-dimethylamino)ethanol whereby a mixture of four different structural isomers are 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 .