Synthesis of zinc phthalocyanine containing 1,2-phenylene bis(3-chloropropanoate) substituted groups and investigation of their metabolic enzyme inhibitory effects

In this study, 4,5-dicyano-1,2-phenylene dinicotinate compound was obtained as a result of the reaction of 4,5-dichlorophthalonitrile and nicotinic acid. This compound was reacted with the zinc chloride salt to obtain the original zinc phthalocyanine compound bearing 1,2-phenylene bis(3-chloropropanoate) substituted groups. This compound and its starting material were characterized with the assist of ¹H NMR, IR, UV–vis, Mass spectrum. In the docking study of compounds (3) and (4) against each target (AChE, BChE, α-Amy and α-Gly), Zn complex (4) exhibits more binding affinity with the target models considered compared to ligand structure (3). Especially, AChE protein and complex (4) form the best binding affinity with a binding energy value of −10.55 kcal/mol. They are compatible and supportive with the data obtained as a result of in vitro analysis. These 4,5-dicyano-1,2-phenylene dinicotinate (3) and 2, 10, 16, 24 – tetrakis 1,2-phenylene bis(3-chloropropanoate) phthalocyaninato) zinc(II) (4) complexes had effective inhibition against α-glucosidase, α-amylase, butyrylcholinesterase and AChE. Also, IC₅₀ amounts were found as 7.84 and 12.36 µM for AChE, 3.80 and 4.56  µM for BChE, 27.08 and 38.14  µM for α-amylase, and 5.30 and 9.73  µM for α-glucosidase.