Spectroscopy and solvatochromism studies along with antioxidant and antibacterial activities investigation of azo-azomethine compounds 2-(2-hydroxyphenylimino)methyl)-4-phenyldiazenyl)phenol.
The azo-azomethine compounds 2-(2-hydroxyphenylimino)methyl)-4-phenyldiazenyl)phenol (2a-d) were prepared from the reaction of 2-aminophenol with 2-hydroxy-5-(aryldiazenyl)benzaldehyde (1a-d). The structures of all compounds were then characterized by elemental analysis, mass, infrared, UV-vis, (1)H and (13)C NMR spectroscopy. The electronic absorption spectra indicated enol-keto tautomeric and positive solvatochromism in compounds (2a-d), which is dependent on the substitution, nature of solvent, pH and environment temperature. The compounds (2a-d) were also evaluated for antibiotic activities by disc diffusion method. Compounds 2a and 2b exhibited antibacterial activities against Staphylococcus aureus and Bacillus cereus, but 2c and 2d were found to have no remarkable antibacterial activity. All the compounds (2a-d) also showed antioxidant activity as determined by 1,1-diphenyl-2-picryl-hydrazyl (DPPH) method.
Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
Motaleb
M
Ghasemian
Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran. Electronic address: kakanejadi.a@lu.ac.ir.
Ali
A
Kakanejadifard
Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
Farideh
F
Azarbani
Department of Chemistry, Faculty of Science, Lorestan University, Khorramabad, Iran.
Abedin
A
Zabardasti
Department of Biology, Faculty of Science, Lorestan University, Khorramabad, Iran.
Sahar
S
Kakanejadifard
D000814:Aniline Compounds / Q000494:pharmacology*; D000900:Anti-Bacterial Agents / Q000494:pharmacology*; D000975:Antioxidants / Q000494:pharmacology*; D001391:Azo Compounds / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D004055:Differential Thermal Analysis; D004583:Electrons; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D066244:Proton Magnetic Resonance Spectroscopy; D011789:Quantum Theory; D012997:Solvents / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D013818:Thermogravimetry
D000814:Aniline Compounds; D000900:Anti-Bacterial Agents; D000975:Antioxidants; D001391:Azo Compounds; D012997:Solvents
Antibacterial activity; Antioxidant activity; Azo–azomethine; Enol–keto tautomeric; Schiff base; Solvatochromism