Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and <i>in vitro</i> antimicrobial activity

The synthesis of novel metallophthalocyanines (M = Zn, Mg, and Co) derived from ( E)-3-(3-bromophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one and ( E)-3-(3-fluorophenyl)-1-(3-hydroxyphenyl)prop-2-en-1-one is achieved. These complexes and the synthesized novel phthalonitrile derivatives are characterized by FTIR, 1H NMR, 13C NMR, UV-Vis, mass spectrometry, and elemental analysis. The aggregation properties of the metallophthalocyanines ZnPc, MgPc, and CoPc are investigated in different solvents and at different concentrations in dimethyl formamide. The electrochemical behavior is also investigated. The cyclic voltammograms give one oxidation reaction for all the bromo-derived metallophthalocyanines and one reduction reaction for all the fluoro-derived metallophthalocyanines. Fe3+, Cd2+, Hg2+, Cu2+, Ni2+, and Co2+ ions are titrated fluorometrically with the phthalocyanines. The bromo- and fluoro-substituted phthalocyanine compounds show different effects on the metal ion titrations.

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“…Due to the paramagnetic nature of complexes 3c and 4c , the 1 H NMR spectra of these compounds could not be determined. 28…”

Section: Resultsmentioning

confidence: 99%

New chalcone-substituted metallophthalocyanines: Synthesis, characterization, and investigation of their properties

Kamiloğlu

Karaca

Çelik

et al. 2020

Journal of Chemical Research

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“…Moreover, eugenol can be used as a scaffold to synthesize biologically active natural products [ 183 , 184 ]. The possibility to introduce eugenol skeleton in complex structures such as phthalocyanines [ 185 ], platinum(II) complexes [ 186 ], and organic antimicrobial polymers [ 187 ] has been explored, obtaining new interesting biologically active species ( Figure 3 ).…”

Section: Monophenolsmentioning

confidence: 99%

“… Structure of eugenol phthalocyanine derivative ( EUG-1 ) [ 185 ] and eugenol Pt(II) complexes EUG-2-4 [ 186 ]. …”

Section: Figures Schemes and Tablesmentioning

confidence: 99%

Tailored Functionalization of Natural Phenols to Improve Biological Activity

et al. 2021

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Phenols are widespread in nature, being the major components of several plants and essential oils. Natural phenols’ anti-microbial, anti-bacterial, anti-oxidant, pharmacological and nutritional properties are, nowadays, well established. Hence, given their peculiar biological role, numerous studies are currently ongoing to overcome their limitations, as well as to enhance their activity. In this review, the functionalization of selected natural phenols is critically examined, mainly highlighting their improved bioactivity after the proper chemical transformations. In particular, functionalization of the most abundant naturally occurring monophenols, diphenols, lipidic phenols, phenolic acids, polyphenols and curcumin derivatives is explored.

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“…Substituted metal phthalocyanine complexes and their gold nanoparticle and graphene conjugates have been known to exhibit antibacterial and photodynamic antibacterial activities. Representative precedents are mentioned here [28][29][30][31][32].…”

Section: Introductionmentioning

confidence: 99%

Antifungal Activity and Staining Properties of Some Symmetrically Functionalized Metal Phthalocyanine Dyes

Somashekarappa¹,

Keshavayya²

2022

JASR

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Effects of 1, 8, 15, 22-tetranitro Co(II) and Zn(II) phthalocyanines [3-NO2CoPc, 3-NO2ZnPc], 1,8,15,22-tetracyano Co(II) phthalocyanine [3-CNCoPc] and 2, 9, 16, 23-tetranitro iron(III)chlorophthalocyanine [4-NO2FePc] on the growth of the fungus Aspergillus niger were studied. All the four complexes inhibited the radial spread of the fungus selected for the study to different extents. A considerable inhibitory effect on growth was seen even in l ppm concentration. The order of inhibitory effect, measured for a period of 5 days is 3-NO2 ZnPc > 3-CNCoPc > 3-NO2CoPc > 4-NO2FePc. The presence of the peripherally substituted phthalocyanine complexes is found to alter the pigmentation property of the selected fungus. Safranin-phthalocyanine double staining technique using 3-NO2CoPc, 3-NO2ZnPc, 4-NO2FePc and 2, 9, 16, 23-tetrahydroxy iron(III)chlorophthalocyanine [4-OHFePc] on the stem sections of Hemidesmus indicus R Br and Polygonum punctatum Buch-Hum have been studied.

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Octa- and tetra-substituted phthalocyanines with methoxyeugenol group: synthesis, characterization and in vitro antimicrobial activity

Cited by 13 publications

References 24 publications

New chalcone-substituted metallophthalocyanines: Synthesis, characterization, and investigation of their properties

New chalcone-substituted metallophthalocyanines: Synthesis, characterization, and investigation of their properties

Tailored Functionalization of Natural Phenols to Improve Biological Activity

Antifungal Activity and Staining Properties of Some Symmetrically Functionalized Metal Phthalocyanine Dyes

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