The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyldiazenyl)phenol

Kakanejadifard, Ali; Azarbani, Farideh; Zabardasti, Abedien; Kakanejadifard, Sahar; Ghasemian, Motaleb; Esna-ashari, Fatemeh; Omidi, Sakineh; Shirali, Somayeh; Rafieefar, Maryam

doi:10.1016/j.dyepig.2012.10.004

Cited by 32 publications

(30 citation statements)

References 28 publications

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“…These chemical shifts propose that azo-azomethine compounds undergo a keto-enol tautomerism that is in agreement with the results obtained from other similar azo Schiff bases [23][24][25][26][27][28][38][39][40]. The 13 C NMR spectra of 3a-e exhibits three signals for the CN-C=C-O, CH=N and C-OH in the ranges of 163.…”

Section: Synthesissupporting

confidence: 85%

“…It shows that enolimine-keto-amine equilibrium is dependent on the pH (Scheme S1). The results indicated that solvatochromism as well as hydrogen bonding and dipole moment of azo-azomethine dyes depends on the nature of substitutions, solvent environment, temperature and acidity of media [23][24][25][26][27][28][38][39][40]. showed lower antibacterial activity than the others.…”

Section: Accepted Manuscriptmentioning

confidence: 90%

“…The UV-Vis absorption spectra of 3a-e in these solvents indicate one band at 340-363 nm due to π→π* transition of the aromatic ring involving the π electrons of the azomethine groups and a red shift similar to the same spectra of azo-Schiff bases [23][24][25][26][27][28][38][39]. In addition, the electronic absorption spectra of 3a-e in DMF…”

Section: Figurementioning

confidence: 93%

“…7 solvent shows another broad band in the range of 447-453nm that can be assigned to an n→π* electronic transition of azo-aromatic chromophore and intramolecular charge transfer interaction like the other dyes [23][24][25][26][27][28][38][39][40].The intramolecular charge transfer bands can be assigned to the existence of enol-keto equilibrium originating from hydrogen transferred form hydroxyl group to imine or azo nitrogen. The absorption bands at 447-453 nm in DMF show bathochromic shift with polarity change of solvent (Fig.…”

Section: Accepted Manuscriptmentioning

confidence: 96%

“…S1). It shows that the positive solvatochromism may be due to the effect of other causes such as dipole moment changes and the hydrogen bonding strength in polar solvents [23][24][25][26][27][28]. The absorption curves of 3a-e in DMF solvent are shown in Fig.…”

Section: Accepted Manuscriptmentioning

confidence: 98%

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Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Kakanejadifard

Azarbani

Khosravani

et al. 2016

Journal of Molecular Liquids

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Section: Synthesissupporting

confidence: 85%

Section: Accepted Manuscriptmentioning

confidence: 90%

Section: Figurementioning

confidence: 93%

Section: Accepted Manuscriptmentioning

confidence: 96%

Section: Accepted Manuscriptmentioning

confidence: 98%

See 3 more Smart Citations

Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Kakanejadifard

Azarbani

Khosravani

et al. 2016

Journal of Molecular Liquids

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Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Mahmoud

Sayed

Mohamed

2016

Applied Organom Chemis

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A new azo dye with N3O2 donor set of atoms has been synthesized via coupling reaction of 2,6-diaminopyridine with p-methoxybenzaldehyde. The molecular and electronic structure of the azo dye ligand (L) was optimized theoretically and the quantum chemical parameters were calculated. Molecular docking was used to predict the binding between L and the receptors of breast cancer mutant 3hb5-oxidoreductase, crystal structure of Escherichia coli (3 T88) and crystal structure of Staphylococcus aureus (3q8u). The newly synthesized L was used for complex formation with Cr(III), Mn(II), Fe(III), Co.(II), Ni(II), Cu(II), Zn(II) and Cd (II) ions. The nature of bonding and the stoichiometry of L and its mononuclear complexes were deduced from elemental analyses, spectroscopic, magnetic susceptibility, molar conductance, electron spin resonance and conductivity measurements, thermogravimetric analyses and powder X-ray diffraction. Elemental analysis data show that the complexes have composition of ML type with an octahedral geometry for all the complexes. The activation thermodynamic parameters were calculated. The prepared azo dye and its metal complexes were tested against various Gram-positive and Gram-negative bacteria and a fungus. Most complexes exhibit antibacterial and antifungal activities against these organisms. Anticancer evaluation studies against standard breast cancer cell line were performed using various concentrations. The activity index was calculated.

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Azo dye with nitrogen donor sets of atoms and its metal complexes: Synthesis, characterization, DFT, biological, anticancer and Molecular docking studies

Mahmoud

Sayed

2018

Applied Organom Chemis

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An azo derivative was synthesized by coupling diazotized 2,6-diaminopyridine with p-dimethyl amino benzaldehyde and this new ligand formed a series of metal complexes with Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II) and Cd(II) salts. These complexes were characterized on the basis of elemental analyses, molar conductance, infrared spectroscopy, UV-Vis, 1 H NMR, mass spectrometry, electronic spectra, magnetic susceptibility and ESR spectral studies, conductivity measurements, thermogravimetric analyses (TG-DTG). The molecular and electronic structure of the azo ligand was optimized theoretically and the quantum chemical parameters were calculated. The ligand and its metal complexes were subjected to X-ray powder diffraction study. The thermal stability of the ligand and its metal complexes was examined by thermogravimetry. The ligand and its complexes were tested for their in vitro antimicrobial activity, some of the complexes showed good antimicrobial activities against some selected bacterial and fungal strains. Anticancer activity of the ligand and its metal complexes are evaluated against human cancer (MCF-7 cells viability). Molecular docking was used to predict the binding between azo ligand and the receptors of nucleoside diphosphate kinase of Staphylococcus aureus (3Q8U) and (3HB5) which is breast cancer mutant oxidoreductase. The docking study provided useful structural information for inhibition studies.

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The synthesis, structural characterization and antibacterial properties of some 2-((4-amino-1,2,5-oxadiazol-3-ylimino)methyl)-4-(phenyldiazenyl)phenol

Cited by 32 publications

References 28 publications

Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Synthesis, structural characterization, X-ray, solvatochromism and biological properties of 7-hydroxy-2-(2-hydroxy-5-(phenyldiazenyl)benzylidene)amino)-4-phenyl-4H-chromene-3-carbonitrile

Synthesis, characterization and in vitro antimicrobial and anti‐breast cancer activity studies of metal complexes of novel pentadentate azo dye ligand

Azo dye with nitrogen donor sets of atoms and its metal complexes: Synthesis, characterization, DFT, biological, anticancer and Molecular docking studies

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