Design, synthesis of novel peripherally tetra-chalcone substituted phthalocyanines and their inhibitory effects on acetylcholinesterase and carbonic anhydrases (hCA I and II)

Abstract

In this work, phthalocyanine precursor (3), tetra-chalcone substituted metal-free (4) and metallo phthalocyanines (5, 6, 7) were synthesized for the first time and surveyed interactions against acetylcholinesterase (AChE, which are associated with Alzheimer's disease) and human CA isoenzymes I and II (hCA I and hCA II, which are ubiquitous cytosolic isoforms). The structures of the novel phthalonitrile (3) and phthalocyanines (4-7) were designated by FT-IR, NMR, UV-Vis, and mass spectroscopy. These phthalocyanines inhibited hCA I with inhibition constants in the range of 0.5621-0.6413 μM and hCA II with inhibition constants in the range of 0.4823-0.6117 μM. On the other hand, these phthalocyanines indicated notable inhibitory effect against AChE.