In this paper, phthalonitrile (3) and non-peripherally tetra triclosan (5-chloro-2-(2,4-dichlorophenoxy) phenol) substituted phthalocyanine (4) and its metallo-phthalocyanine derivatives (5 and 6) were prepared. The structures of novel compounds (3-6) were characterized by spectrophotometric measurements. The acetylcholinesterase (AChE) from Electrophorus electricus, butyrylcholinesterase (BuChE) from equine serum, alpha-glucosidase from Saccharomyces cerevisiae, 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging properties of the compounds (3-6) were investigated using spectrophotometric method. The supercoiled plasmid pBR322 DNA hydrolytic nuclease effects of the compounds (3-6) were investigated on the agarose gel. The compound 5 showed the strongest AChE and BuChE inhibitory properties with IC50 values of 0.86 +/- 0.01 and 20.46 +/- 2.47 mu M, respectively and the SI value of 5 was 23.79. Also, 5 showed the highest alpha-glucosidase inhibitory and DPPH radical scavenging actions with IC50 values of 25.12 +/- 0.62 mu M and 1.11 +/- 0.02 mu M, respectively. The compounds showed no hydrolytic nuclease effects at increasing concentrations against supercoiled plasmid DNA. These results showed that 5 may be a lead compound for further research to develop a novel inhibitor for the treatments of Alzheimer's diseases and Diabetes mellitus. (C) 2020 Elsevier B.V. All rights reserved.