Abstract In this study, the novel phthalonitrile derivatives 1 and 2 were synthesized. Tetra-substituted metal-free 1a (H2Pc) and metallophthalocyanines (ZnPc 1b, CoPc 1c and CuPc 1d) bearing four peripheral 4-allyl-2,6-dimethoxyphenol (methoxy-eugenol) groups and octa-substituted metal-free 2a and metallophthalocyanines (ZnPc 2b, CoPc 2c and CuPc 2d) bearing eight peripheral methoxy-eugenol group were synthesized. All new synthesized compounds are characterized by IR, 13C{1H} NMR (for 1 and 2), UV-Vis (for 1a–2d) and mass spectroscopy. Antimicrobial activities of the synthesized phthalonitrile derivatives (1 and 2) and phthalocyanine compounds 1a–2d were determined by microdilution broth method against nine different bacteria and one yeast species. In this study, CoPc (2c) compound, which has eight peripheral 4-allyl-2,6-dimethoxyphenol, had the highest antibacterial activity (minimum inhibitory concentration [MIC] = 312 μg/mL). In addition, 1b, 1d, 2b and 2d were found to be effective on at least three different bacterial species at different concentrations (MIC = 1250–5000 μg/mL). Shigella flexneri were the most affected bacteria, but none of the compounds were effective against fungal isolate. Graphical Abstract

中文翻译：

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具有甲氧基丁香酚基团的八取代和四取代酞菁：合成、表征和体外抗菌活性

摘要 本研究合成了新型邻苯二甲腈衍生物1和2。四取代的无金属 1a (H2Pc) 和金属酞菁（ZnPc 1b、CoPc 1c 和 CuPc 1d）带有四个外围 4-烯丙基-2,6-二甲氧基苯酚（甲氧基丁香酚）基团和八取代的无金属 2a 和金属酞菁合成了带有八个外围甲氧基丁香酚基团的 (ZnPc 2b、CoPc 2c 和 CuPc 2d)。所有新合成的化合物均通过 IR、13C{1H} NMR（对于 1 和 2）、UV-Vis（对于 1a-2d）和质谱进行表征。通过微量稀释肉汤法测定合成的邻苯二甲腈衍生物（1 和 2）和酞菁化合物 1a-2d 对九种不同细菌和一种酵母菌的抗菌活性。在这项研究中，CoPc (2c) 化合物，它有八个外围 4-烯丙基-2,6-二甲氧基苯酚，具有最高的抗菌活性（最低抑菌浓度 [MIC] = 312 μg/mL）。此外，发现 1b、1d、2b 和 2d 对至少三种不同浓度的细菌有效（MIC = 1250–5000 μg/mL）。弗氏志贺氏菌是受影响最大的细菌，但没有一种化合物对真菌分离物有效。图形概要