In vitro antibacterial, radical scavenging and solvato-chromism properties of some 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino)methyl) phenols

doi:10.1007/s13738-016-0970-3

Paper

In vitro antibacterial, radical scavenging and solvato-chromism properties of some 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino)methyl) phenols

Published 2016 · Farideh Azarbani, A. Kakanejadifard, Vahid Nadri

Journal of the Iranian Chemical Society

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Abstract

The 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino) methyl) phenols were synthesized from the reaction of 5-((4-R-phenyl)diazenyl)-2-hydroxybenzaldehyde with aminopyridines in absolute ethanol and characterized by elemental analysis, mass, FT-IR, UV and NMR spectroscopy. The absorption maxima of synthesized compounds show bathochromic shift in various solvents. The nature of substitutions, solvent environment, hydrogen bonds, temperature, pH and dipole moment of the molecules are the key factors in deciding the solvato-chromism of azo–azomethine dyes. Antibacterial activity was studied by disk diffusion and broth microdilution methods. Diphenylpicrylhydrazyl assay was used to determine the radical scavenging properties. Compounds having electron donating groups in the aryl azo component showed significant antibacterial activity against Bacillus cereus, Staphylococcus aureus, Escherichia coli and Klebsiella pneumonia. Derivative 2-((E)-(pyridin-4-ylimino) methyl)-4-((E)-p-tolyldiazenyl) phenol (2h) with excellent antibacterial activity showed the highest scavenging effect, while the minimum antibacterial and scavenging activity was observed by 4-((E)-(4-chlorophenyl)diazenyl)-2-((E)-(pyridin-2-ylimino)methyl) phenol (2f) having electron withdrawing Cl substituent in the aryl azo component. The antibacterial and scavenging activity of synthesized derivatives are affected by the nature and position of the substituent groups and position of the nitrogen atoms in the pyridine ring.Graphical AbstractThe aminopyridine-based azo–azomethine compounds have been synthesized by condensation reaction of 5-((4-R-phenyl)diazenyl)-2-hydroxybenzaldehyde with n-aminopyridine. The spectra indicated positive solvato-chromism in prepared substances which is dependent on the solvent, substitution, pH and temperature. All the synthesized azo Schiff bases except 2f showed significant antibacterial activity.

Study Snapshot

4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino)methyl) phenols show significant antibacterial activity against various bacteria, with their antibacterial and scavenging properties influenced by substituent groups and nitrogen atom positions.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

In vitro antibacterial, radical scavenging and solvato-chromism properties of some 4-((4-R-phenyldiazenyl-2-(pyridin-2-ylimino)methyl) phenols

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Citations

Solvent, structural, quantum chemical study and antioxidative activity of symmetrical 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides

Symmetric 1-methyl-2,6-bis[2-(substituted phenyl)ethenyl]pyridinium iodides show moderate antioxidant potential due to their unique structure and electronic transition dependence.