Synthesis, characterization, spectroscopy and biological activity of 4-((3-formyl-4-hydroxyphenyl)azo)-1-alkylpyridinium salts
Abstract
The reaction of 2-hydroxy-5-(pyridine-4-yldiazenyl)benzaldehyde with n-alkyl bromides generated five novel azo pyridinium salts in good to excellent yields. The \(^{1}\hbox {H}\) and \(^{13}\hbox {C}\) NMR and UV-Vis absorption spectra indicated several tautomers for the new compounds. The NMR, UV-Vis absorption spectra and quantum chemical calculations show that the azo pyridinium salts have a new resonant structure compared to the corresponding azo precursor. Antibacterial activity was studied by disc diffusion and MIC methods. Diphenylpicrylhydrazyl (DPPH) assay was used to determine the antioxidant properties. The effects of carbon chain length on antimicrobial activity were also investigated. The results showed that existence of alkyl groups is crucial for the antibacterial properties. The new compound with decyl group displayed the best antibacterial activity.
Graphical Abstract
SYNOPSIS Five novel azo pyridinium salts were synthesized in high yield. Resonant structures in azo pyridinuim were studied by
\(^{1}\hbox {H}\)
NMR and UV-Vis spectra. Antibacterial and antioxidant properties were also investigated.
Publisher URL: https://link.springer.com/article/10.1007/s12039-018-1521-5
DOI: 10.1007/s12039-018-1521-5
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