Synthesis, characterization and spectroscopic properties of some new azo disperse dyes derived from 4-hydroxybenzo[h]quinolin-2-(1H)-one as a new synthesized enol type coupling component

Rufchahi, E.O. Moradi; Gilani, A. Ghanadzadeh

doi:10.1016/j.dyepig.2012.06.008

Cited by 45 publications

(28 citation statements)

References 24 publications

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“…Also, IR spectra did not reveal broad signal at 3434 cm −1 , which is characteristic for OH of azo-enol form. 30) These spectroscopic analysis allows to rule out the azo-enol form (B) and CH-azo form (C) (Fig. 1).…”

Section: Resultsmentioning

confidence: 99%

Azoles and <i>bis</i>-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

Kheder

Riyadh

Asiry

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Resultsmentioning

confidence: 99%

Azoles and <i>bis</i>-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

Kheder

Riyadh

Asiry

2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Many reports have been published for diazotization and also for azo-coupling reactions in literature [5][6][7]. However, many of these reported methods suffer from one or more practical drawbacks associated with hazardous reagents, long reaction times, less effective catalysts, formation of side products and difficult and time consumed work-up procedure.…”

Section: Introductionmentioning

confidence: 98%

“…1 Hz); 5.31 (1H, s-br);13 C NMR (100 MHz, DMSO-d6 ) δ (ppm): 161.3, 152.8, 146.3, 131.8, 129.1, 125.5, 124.7, 122.0, 116.4, 116.1. Anal.…”

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confidence: 99%

“…H NMR (400 MHz, DMSO-d6 ) δ (ppm): 8.55 (1H, d, J = 8.2 Hz); 8.11 (1H, d, J = 1.6 Hz); 7.96 (1H, d, J = 9.4 Hz); 7.80 (2H, d, J = 8.2 Hz); 7.62 (2H, t, J = 8.2 Hz); 7.51 (1H, d, J = 10.1 Hz); 7.45 (1H, d, J = 10.1 Hz); 6.965 (1H, d, J = 9.4 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ (ppm): 148.6, 148.1, 147.6, 138.: FT-IR (KBr, cm -1 ): 3411 (bs), 1650, 1613. 1 H NMR (400 MHz, CDCl 3 ) δ (ppm): 12.16 (OH, s), 8.58 (1H, dd, J = 8.13 and 2.03 Hz); 7.85 (2H, d, J = 7.88 Hz); 7.68 (2H, d, J = 7.88); 7.51 (1H, d, J = 7.28 Hz); 7.49 (1H, d, J = 7.28 Hz); 7.45 (1H, dd, J = 7.95 and 2.02 Hz); 7.43 (1H, dt, J = 7.65 and 1.99 Hz); 7.42 (1H, dt, J = 7.75 and 1.97 Hz); 13 C NMR (100 MHz, CDCl 3 ) δ (ppm): 143.33, 137.30, 134.15, 131.15, 128.47, 127.87, 124.12, 121.33, 120.13, 119.35, 119.23, 117.14, 115.71, 111.18.…”

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confidence: 99%

“…Infrared spectra were recorded in KBr and determined on a Perkin Elmer FT-IR spectrometer. 1 HNMR and 13 CNMR spectra were recorded on a Bruker Avance AC-400 MHz using DMSO-d6 or CDCl 3 as the deuterated solvent and TMS as internal standard. All melting point measured in open glass-capillaries using a Stuart melting point apparatus.…”

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confidence: 99%

See 2 more Smart Citations

Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions

et al. 2015

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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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Synthesis, characterization and spectroscopic properties of some new azo disperse dyes derived from 4-hydroxybenzo[h]quinolin-2-(1H)-one as a new synthesized enol type coupling component

Cited by 45 publications

References 24 publications

Azoles and <i>bis</i>-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

Azoles and <i>bis</i>-Azoles: Synthesis and Biological Evaluation as Antimicrobial and Anti-cancer Agents

Synthesis of a nitrite functionalized star-like poly ionic compound as a highly efficient nitrosonium source and catalyst for the diazotization of anilines and subsequent facile synthesis of azo dyes under solvent-free conditions

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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