Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity
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CitationAktas Kamiloglu, A., Direkel, S., Yalazan, H., Kantekin, H., & Acar, I. (2020). Octa-and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity. Journal of Coordination Chemistry, 73(7), 1177-1190
In this study, the novel phthalonitrile derivatives1and2weresynthesized. Tetra-substituted metal-free1a(H2Pc) and metalloph-thalocyanines (ZnPc1b,CoPc1cand CuPc1d) bearing four per-ipheral 4-allyl-2,6-dimethoxyphenol (methoxy-eugenol) groupsand octa-substituted metal-free2aand metallophthalocyanines(ZnPc2b,CoPc2cand CuPc2d) bearing eight peripheralmethoxy-eugenol group were synthesized. All new synthesizedcompounds are characterized by IR,13Cf1HgNMR (for1and2),UV-Vis (for1a–2d) and mass spectroscopy. Antimicrobial activitiesof the synthesized phthalonitrile derivatives (1and2) andphthalocyanine compounds1a–2dwere determined by microdi-lution broth method against nine different bacteria and one yeastspecies. In this study, CoPc (2c) compound, which has eight per-ipheral 4-allyl-2,6-dimethoxyphenol, had the highest antibacterialactivity (minimum inhibitory concentration [MIC]¼312lg/mL). Inaddition,1b,1d,2band2dwere found to be effective on atleast three different bacterial species at different concentrations(MIC¼1250–5000lg/mL).Shigella flexneriwere the most affectedbacteria, but none of the compounds were effective against fun-gal isolate.