(S)-(4-(Prop-1-en-2-yl)cyclohex-1-enyl)methanol Substituted Phthalocyanines: Synthesis, Photochemical and Photophysical Properties, and Enzyme Inhibition Behaviors

Abstract

In this study, (S)-4-((4-(prop-1-en-2-yl)cyclohex-1-enyl)methoxy)phthalonitrile, as a novel phthalonitrile derivative, which is the starting material for phthalocyanine synthesis, was prepared and characterized. Then, its symmetric metal-free [H₂Pc (2)] and metallophthalocyanine derivatives [ZnPc (3), CuPc (4), and CoPc (5)] were successfully synthesized, and their structures were characterized with the combination of suitable spectroscopic methods. The solubility and aggregation properties of novel phthalocyanines were investigated. Also, the photophysical and photochemical properties of the newly synthesized H₂Pc (2) and ZnPc (3) were studied in solution media. The singlet oxygen quantum values are 0.45 for H₂Pc (2) and 0.75 for ZnPc (3). According to these results, the peripheral perillyl alcohol substitution of phthalocyanines increased the therapeutic efficacy. At the same time, the newly synthesized phthalocyanines (2–5) displayed the strongest inhibitory effect. The results indicate a high affinity and selectivity for carbonic anhydrases. This underscores their potential as promising lead compounds for developing therapeutic agents to treat conditions such as glaucoma, epilepsy, and certain types of cancer.