Applied Organometallic Chemistry, cilt.38, sa.5, 2024 (SCI-Expanded)
In this work, a series of aldehyde-substituted phthalocyanine compounds (1, 3, and 5) were prepared by the cyclotetramerization of the 4-(5-(diethylamino)-2-formylphenoxy) phthalonitrile (a) and the corresponding metal salts. Schiff base-substituted phthalocyanines (2, 4, and 6) were derived from an aldehyde-substituted phthalocyanine (1, 3, and 5) via the reaction of aldehyde-substituted phthalocyanines with an amine reagent. The compounds that were obtained were characterized using FT-IR, 1H {13C} NMR, UV–Vis, and MS spectra (a and 1–6). The inhibitory qualities of synthesized aldehyde and Schiff base-substituted complexes against the enzymes butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) were assessed. The majority of phthalocyanines exhibited strong enzyme-inhibiting properties. Out of the six produced phthalocyanines, 3 and 4 displayed the most intriguing profiles as submicromolar selective AChE inhibitors (IC50 = 0.060 μM), whereas 1 demonstrated the most potent BChE inhibitor (IC50 = 0.024 μM). The aggregation studies of CoPcs, CuPcs, and ZnPcs (1–6) were also carried out in this work.