SYNTHESIS AND PHOTOCYTOTOXICITY OF SOME NEW SUBSTITUTED PHTHALOCYANINES

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Abstract
Some new, ring‐substituted phthalocyanines have been synthesized and underwent preliminary testing for photodynamic activity using the colony forming ability of Chinese hamster cells in culture as an endpoint. Using 4‐(3‐N, N‐diethylaminopropyl)phthalonitrile as a precursor, the previously unknown metal‐free 2,9,16,23‐tetra‐(3‐N, N‐diethylaminopropyl)phthalocyanine was prepared and converted to its zinc (II) and its cationic water‐soluble 2,9,16,23‐tetramethylammonium zinc (II) iodide derivatives. Other new phthalocyanine derivatives tested, include a 2,9,16,23‐tetra(2‐hydroxymethyl‐2‐methyIbutoxy)phthalocyaninato zinc (II) and 2,3,9,10,16,17,23,24‐octahydroxyphthalocyaninato zinc (II) derivatives. Boron tribromide cleavage of the newly prepared and fully characterized 2,3,9,10,16,17,23,24‐octamethoxyphthalocyanine gave the unstable metal‐free octahydroxyphthalocy‐anine, which could only be characterized by ultraviolet‐visible, NMR and IR spectroscopy.