Synthesis and Characterization of New Azopyrimidine Complexes

Z)-5-((1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)diazenyl)-6hydroxy-2-mercaptopyrimidin-4(3H)-one (H 3 L) was exploited as a ligand for the synthesis of a series of metal complexes, where the metal was Mn(II), Co(II), Ni(II), Cu(II), Zn(II), Pd(II), Cr(III) and Ru(III). The structural features of the ligand and the synthesized complexes were characterized using various analytical, spectral and thermal measurements. Infrared spectra showed that the ligand coordinates to all metal ions in a neutral keto-enol-thiol manner. It behaves in a tetradentate fashion in all binuclear complexes except the Cr(III) complex, where it is hexadentate, and in a tridentate fashion in mononuclear complexes. The azo group participates in chelation only in the case of binuclear complexes. All complexes exhibit octahedral geometry except Pd(II) and Cu(II) acetate which are square planar and square pyramidal, respectively. Kinetic parameters were computed from thermal decomposition data. Axial electron spin resonance spectra were obtained for Cu(II) complexes indicating (d x 2 −y 2 ) 1 as a ground state with small g || values affording strong interaction between the ligand and metal ions. The biological measurements reveal that the ligand has antioxidant activity relative to the metal complexes, while the metal complexes have cytotoxicity in comparison to the free ligand. KEYWORDSantioxidant and anticancer activity, azodye ligand, metal complexes, spectral methods, thermal studies

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Synthesis, spectral characterization, thermal studies and biological activity of (Z)‐5‐((1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)diazenyl)‐6‐hydroxy‐2‐mercaptopyrimidin‐4(3H)‐one and its metal complexes

Emam

Abouel‐Enein

Abouzayed

2017

Applied Organom Chemis

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Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Abouel‐Enein

Emam

Monir

2018

Applied Organom Chemis

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Nine new azodye metal complexes of Mn(II), Co(II), Ni(II), Cu(II), Cr(III), Fe(III), Ru(III), Hf(IV) and Zr(IV) ions have been prepared via the reaction of 5,5′‐((1E,1′E)‐(methylenebis(1,4‐phenylene))bis(diazene‐2,1‐diyl))bis(6‐hydroxy‐2‐thioxo‐2,3‐dihydropyrimidin‐4(5H)‐one) (H4L) with the corresponding metal salts affording sandwich (1 L:1 M), mononuclear (2 L:1 M), binuclear (1 L,2 M) and tetranuclear (1 L,4 M) complexes. Elemental analyses, spectral methods, magnetic moment measurements and thermal studies were utilized to confirm the mode of bonding and geometrical structure for the ligand and its metal complexes. Infrared spectral data show that the H4L ligand chelates with some metal ions in keto–enol–thione or keto–thione manner. It behaves in a neutral/dibasic tetradentate fashion in sandwich and binuclear complexes. Also, it acts as a neutral bidentate moiety in the Cr(III) complex. The spectra reveal that azo group participates in chelation in all complexes. Octahedral geometry was suggested for all chelates but the Cu(II) complex with square planar geometry. The thermal stability and decomposition of the compounds were studied, the data showing that the thermal decomposition ended with metal or metal oxide mixed with carbon as final product. The electron spin resonance spectrum of the Cu(II) complex demonstrates that the free electron is located in the ( dx2−y2) orbital. Measurements of biological activity against human cell lines Hep‐G2 and MCF‐7 reveal that the Cu(II) complex has a higher cytotoxicity in comparison to the free ligand and other metal complexes, with IC50 values of 6.10 and 5.2 μg ml−1, respectively, while the ligand has anti‐tumour activity relative to some of the investigated metal complexes.

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Photophysical and Complexation Behavior of (4‐Dimethylamino‐benzylidene)‐(4,6‐dimethyl‐pyrimidin‐2‐yl)‐amine

El-Sayed

Fayed²,

Gaber

2010

Chin. J. Chem.

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The absorption and fluorescence characteristics of (4-dimethylamino-benzylidene)-(4,6-dimethyl-pyrimidin-2yl)-amine (SB) have been investigated in different solvents. Both the absorption and emission spectra of SB exhibit red shifts as the solvent polarity increases. This indicats a change in dipole moment of molecules upon excitation as a result of intramolecular charge transfer interaction. The fluorescence quantum yield depends strongly on the properties of the solvents, which was discussed on the bases of positive and negative solvatokinetic effects. The effect of some divalent transition metal ions such as Mn 2＋ , Co 2＋ , Ni 2＋ , Cu 2＋ , Zn 2＋ , Cd 2＋ , and Hg 2＋ on the absorption and fluorescence spectra of SB is also investigated. The results were consistent with formation of highly colored metal-SB complex which is responsible for the extreme quenching of the fluorescence of SB. The variations of both the formation constant of the complex and Stern-Volmer constant were correlated with the electronic structure of the used metal ion.

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Synthesis and Characterization of New Azopyrimidine Complexes

Cited by 43 publications

References 38 publications

Synthesis, spectral characterization, thermal studies and biological activity of (Z)‐5‐((1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)diazenyl)‐6‐hydroxy‐2‐mercaptopyrimidin‐4(3H)‐one and its metal complexes

Synthesis, spectral characterization, thermal studies and biological activity of (Z)‐5‐((1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)diazenyl)‐6‐hydroxy‐2‐mercaptopyrimidin‐4(3H)‐one and its metal complexes

Coordination modes of multidentate azodye ligand derived from 4,4′‐methylenedianiline towards some transition metal ions: Synthesis, spectral characterization, thermal investigation and biological activity

Photophysical and Complexation Behavior of (4‐Dimethylamino‐benzylidene)‐(4,6‐dimethyl‐pyrimidin‐2‐yl)‐amine

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