Synthesis of new 1,2,3-triazole substituted phthalocyanines by click reaction and investigation of their activities on acetylcholinesterase enzyme

In this study, firstly, 2-(2-azido-ethoxy)-ethanol (1) was synthesized from the 2-(2-chloro-ethoxy)-ethanol according to the literature. Secondly, 2-(2-(4-((Dimethylamino)methyl)-1H-1,2,3-triazolile)ethoksi)ethanol (2) was synthesized by the click reaction between 3-dimethylamino-1-propyne and 2-(2-azido-ethoxy)-ethanol (1). In the three stage of the study, the dinitrile derivative (6), which would facilitate our transition to the phthalocyanines, was synthesized by the SNAr type substitution reaction of compound 2 with 4-nitrophthalonitrile. In the last part of the work, 1,2,3-triazole substituted novel metal-free and metallo phthalocyanines (6a-c) and their water soluble derivatives (10a-c) were synthesized by the cyclotetramerization of the dinitrile (6) for the first time and inhibition effects on acetylcholinesterase enzyme were investigated. Keywords: Click reaction, Phthalocyanine, Acetylcholinesterase, Inhibition