RESUMO
The macrocyclic azo-azomethine dyes 2,2'-(((6-methoxy-1,3,5-triazine-2,4-diyl)bis(sulfanediyl)bis(2,1-phenylene))bis(azanylylidene)bis(methanylylidene))bis(4-(phenyldiazenyl)phenol) and its derivatives were synthesized and characterized by elemental analysis, mass, FT-IR, UV-vis and NMR spectroscopy. The solvatochromism as well as effects of substitutions on the electronic absorption of these compounds have been studied in the DMSO, DMF, THF, CH3CN, CH3OH and CH3COOH as solvents. Also they positive solvatochromism behaviors are explained on the basis of intramolecular hydrogen bonding, enol-keto tautomeric and dipole moment changes. Compounds having electron donating substituent on the phenyl ring showed good antioxidant activity. However, none of them has a considerable antibacterial activity.
Assuntos
Compostos Azo/química , Compostos Azo/síntese química , Corantes/química , Corantes/síntese química , Solventes/química , Tiossemicarbazonas/química , Tiossemicarbazonas/síntese química , Triazinas/química , Antioxidantes/farmacologia , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Elétrons , Espectroscopia de Prótons por Ressonância Magnética , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , TemperaturaRESUMO
Azo-azomethine dyes 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyl diazenyl)phenols (2a-h) have been synthesized by condensation reaction of 3,4-diamino-1,2,5-oxadiazole with 2-hydroxy-5-[(E)-(aryldiazenyl)]benzaldehyde (1a-h) in methanol. The structures of dyes have been characterized by elemental analysis, mass, IR, UV-Vis, 1H and 13С NMR spectroscopy. UV-Vis absorption spectra indicated enol-keto tautomeric and positive solvatochromism in compounds 2a-h which is dependent on the substitution, solvent, pH and environment temperature. The synthesized compounds were investigated for their in vitro antioxidant activity by diphenylpicrylhydrazyl assay. Compounds substituted with electron donating groups, such as, alkyl and methoxy groups showed moderate antioxidant activity. The in vitro antibacterial activity of all compounds was determined by disk diffusion method. The test compounds showed varying degree of inhibition against B. cereus and S. aureus strains.
Assuntos
Oxidiazóis/síntese química , Oxidiazóis/farmacologia , Fenol/síntese química , Fenol/farmacologia , Fenóis/síntese química , Fenóis/farmacologia , Solventes/química , Antibacterianos/farmacologia , Bactérias/efeitos dos fármacos , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Dimetil Sulfóxido/química , Dimetilformamida/química , Elétrons , Furanos/química , Testes de Sensibilidade Microbiana , Modelos Moleculares , Oxidiazóis/química , Fenol/química , Fenóis/química , Espectroscopia de Prótons por Ressonância Magnética , Teoria Quântica , Espectrofotometria Ultravioleta , Espectroscopia de Infravermelho com Transformada de Fourier , TemperaturaRESUMO
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.
Assuntos
Compostos de Anilina/farmacologia , Antibacterianos/farmacologia , Antioxidantes/farmacologia , Compostos Azo/farmacologia , Solventes/química , Bactérias/efeitos dos fármacos , Espectroscopia de Ressonância Magnética Nuclear de Carbono-13 , Análise Diferencial Térmica , Elétrons , Testes de Sensibilidade Microbiana , Modelos Moleculares , Espectroscopia de Prótons por Ressonância Magnética , Teoria Quântica , Espectrofotometria Infravermelho , Espectrofotometria Ultravioleta , Temperatura , TermogravimetriaRESUMO
The condensation reaction of 2-hydroxy-5-(aryldiazenyl)benzaldehyde (1a-d) with 2-aminothiophenole affored Schiff base compounds 2-((2-mercaptophenylimino)methyl-4-(-aryldiazenyl)phenol (2a-d). The structures of compounds (2a-d) were characterized by elemental analysis, mass, infrared, UV-vis and NMR spectroscopy. The 2a-d shows enol-keto tautomeric and positive solvatochromism. The antibacterial activities of 2a-d were also evaluated by disc diffusion method. Compound 2b displayed activity against Staphylococcus aureus and Bacillus cereus, 2a and 2c were active against B. cereus but 2d did not exhibit activity against the tested organisms. Among the tested compounds, 2b showed the best antioxidant properties as evaluated by free radical scavenging activity on 1,1-diphenyl-2-picryl-hydrazyl and ferric reducing power determination.
