Synthesis, characterization, antioxidant and antitumor evaluation of new phthalocyanines containing peripherally functionalized fused heterocyclic compounds

Abstract

Our work has been heavily engaged in the synthesis of novel phthalocyanines with various functional groups and/or heterocycles at peripheral and axial positions via the reaction of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) with 1,4-diazabicyclo[2.2.2]octane (DBO). Also, reaction of modified phthalonitrile derivatives 4, 8, 9 and 13 with hydroquinone or DDQ afforded the corresponding new phthalocyanine derivatives 5, 10, 11 and 14, respectively. Moreover, a new generation of phthalocyanine derivatives 17, 21a,b and 25 has been synthesized by cyclotetramerization of phthalic anhydride derivatives 15, 20 a, b and 24 in the presence of 1,3-divinyl-1,1,3,3-tetramethyldisilazane as catalyst. The structures of newly synthesized compounds have been established by both elemental and spectral analyses. The antioxidant activity of the products was screened in series of in vitro tests. In addition, the toxicity of the synthesized compounds was studied at four different cell lines HepG2, WI-38, Vero and MCF-7 cell lines. According to our results, compounds 13 and 14 have a very strong activity against all cell lines and act as good antioxidant agents.