Synthesis, Characterization, Biological Activity and DNA Binding Studies of Metal Complexes with 4‐Aminoantipyrine Schiff Base Ligand

Anupama, B.; Padmaja, M.; Kumari, C. Gyana

doi:10.1155/2012/291850

Cited by 26 publications

(10 citation statements)

References 26 publications

(29 reference statements)

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“…The electronic spectrum of diamagnetic Zn(II) complex showed a band at 511 nm due to metal‐to‐ligand charge transfer. Octahedral geometry was proposed based on its analytical data …”

Section: Resultsmentioning

confidence: 99%

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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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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“…The electronic spectrum of diamagnetic Zn(II) complex showed a band at 511 nm due to metal‐to‐ligand charge transfer. Octahedral geometry was proposed based on its analytical data …”

Section: Resultsmentioning

confidence: 99%

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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“…One of the most significant pyrazolone derivatives is antipyrine. Antipyrine derivatives are reported to exhibit analgesic and anti-inflammatory effects, antiviral and antibacterial activities and have also been used as hair-color additives and to increase the local anesthetic effect of lidocaine (Anupama et al, 2012 (Shakru, 2015). In light of these facts and as a continuation of our work on the synthesis of Schiff bases and hydrazones of the biological active nucleus (Mohamed et al, 2015), the title compound was synthesized.…”

Section: Structure Descriptionmentioning

confidence: 99%

“…One of the most significant pyrazolone derivatives is antipyrine. Antipyrine derivatives are reported to exhibit analgesic and anti-inflammatory effects, antiviral and antibacterial activities and have also been used as hair-color additives and to increase the local anesthetic effect of lidocaine (Anupama et al, 2012). Schiff bases of 4-aminoantipyrine and their metal complexes have a variety of applications in biological, analytical and pharmacological areas.…”

Section: Structure Descriptionmentioning

confidence: 99%

4-{(E)-[(2-Hydroxynaphthalen-1-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: a new polymorph (β-phase)

et al. 2017

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The title molecule, C 22 H 19 N 3 O 2 , is a new polymorphic modification, viz. thephase; the -phase has been previously published [Liang & Wang (2010). Acta Cryst. E66, o1968-o1969]. In the crystal of the -phase, the molecules pack in helical chains generated by C-HÁ Á ÁO hydrogen bonds and offset --stacking interactions. Adjacent chains are associated through C-HÁ Á Á interactions. In the -phase, molecules are linked by C-HÁ Á ÁO and N-HÁ Á ÁO hydrogen bonds, forming layers parallel to the (102) plane. In addition, --stacking interactions and C-HÁ Á Á(ring) interactions consolidate the packing. The packing is compared to that of the -phase. The title compound was refined as a twocomponent twin. Structure descriptionThe chemistry of pyrazolone has gained increasing attention due to its diverse pharmacological properties such as cytotoxic, anti-inflammatory, antimicrobial, antioxidant, antifungal, antiviral, oral hypoglycaemic activity (Kumar et al., 2012). One of the most significant pyrazolone derivatives is antipyrine. Antipyrine derivatives are reported to exhibit analgesic and anti-inflammatory effects, antiviral and antibacterial activities and have also been used as hair-color additives and to increase the local anesthetic effect of lidocaine (Anupama et al., 2012 (Shakru, 2015). In light of these facts and as a continuation of our work on the synthesis of Schiff bases and hydrazones of the biological active nucleus (Mohamed et al., 2015), the title compound was synthesized.Here, we present the crystal structure of a new polymorph (Fig. 1), which we have called the -phase. The -phase corresponds to the crystal form reported earlier (Liang & Wang, 2010).The -phase crystallizes in the monoclinic space group P2 1 /c, with a = 13.7321 (3), b = 6.7719 (2), c = 19.1916 (4) Å , = 99.428 (1) , V = 1760.57 (7) Å 3 and Z = 4 (Table 2), while the -phase crystallizes in the same space group, with a = 8.0636 (7) (15) , respectively. In the -phase, the corresponding angles are similar [147.2 (2) and 115.1 (2) , respectively]. In the -phase, the mean planes of the phenyl ring and the naphthalene moiety make dihedral angles of 56.97 (7) and 12.14 (6), respectively, with that of the central heterocyclic ring, while in the -phase, the corresponding dihedral angles are 50.39 (13) and 11.62 (10) . The dihedral angles between the mean planes of the phenyl ring and the naphthalene ring system in the -and -phases are 61.81 (10) and 64.63 (5) , respectively.In the -phase (Fig. 1), the conformation is partially determined by the intramolecular O2-H1Á Á ÁN3 and C12-H12Á Á ÁO1 hydrogen bonds (Table 1). In the crystal, the molecules form helical chains along the 2 1 axes which involve C4-H4BÁ Á ÁO1 i and C5-H5AÁ Á ÁO2 ii [symmetry codes: (i) x, y + 1, z; (ii) Àx + 1, y + (Table 1 and Fig. 2) as well as pairwise, offset --stacking interactions between the C1-C3/ N1/ N2 and the C17-C22 rings across centers of symmetry (Fig. 3). In these, the distance between centroids is 3.889 (1) Å , the perpendicular distance between the rings is...

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“…The weak peak at (δ8. 14) ppm was attributed to proton of azomethine group (-N=CH-). Single weak peak attributed to proton of (-COOH) appeared at (δ9.30) ppm.…”

Section: H Nmr Spectral Datamentioning

confidence: 99%

“…The spectrophotometric methods are usually based on the reactivity of the aldehyde group [11] [12]. Azido-mixed ligand complexes particular interest has been focused on the azido ligand ( ) 3 N − not only for its efficiency in ferromagnetic or antiferromagnatic coupling but also for its diversity in coordination modes, µ-1, 1, (end-on EO), µ-1, 3 (end-end, EE), µ-1, 1, 1, µ-1, 1, 3 or still other modes and polymetric bridging network, and a large number of azido-bridged complexes with different dimensionalities and various topologies have been reported in the literature [13] [14]. Polynuclear complexes and coordination polymer in which paramagnetic metal ions are bridged by short ligands have attracted great attention in recent years.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Activity of Mixed Ligand (HL) Complexes Mn(ll), Co(ll), Ni(ll), Zn(ll), Cd(ll) and Hg(ll) with Azide (N<sub>3</sub><sup style="margin-left:-6px;">-</sup>)

Sultan¹,

Lateaf²,

Rashid³

2015

OJIC

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The complexes of mixed ligand (HL) as primary ligand with azide ion ( 3 N − ) as co-ligand with Mn(ll), Co(ll), Ni(ll), Zn(ll), Cd(ll) and Hg(ll) were prepared via reaction metal (ll) chloride salt with ligand (HL) and sodium azide (NaN3) using 1:2:2 mole ratio in ethanol solvent, respectively. The complexes of mixed ligand (HL) were characterized by elemental microanalysis (C.H.N), atomic absorption chloride content, molar conductance, magnetic susceptibility, melting point, FTIR and UV-Vis spectral data. The anti bacterial activity with four kinds of bacteria, Staphylococcus aureus, Bacillus, Escherichia coli and Pseudomonas aureus was studied.

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Synthesis, Characterization, Biological Activity and DNA Binding Studies of Metal Complexes with 4‐Aminoantipyrine Schiff Base Ligand

Cited by 26 publications

References 26 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

4-{(E)-[(2-Hydroxynaphthalen-1-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: a new polymorph (β-phase)

Synthesis, Characterization and Antibacterial Activity of Mixed Ligand (HL) Complexes Mn(ll), Co(ll), Ni(ll), Zn(ll), Cd(ll) and Hg(ll) with Azide (N<sub>3</sub><sup style="margin-left:-6px;">-</sup>)

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Synthesis, Characterization, Biological Activity and DNA Binding Studies of Metal Complexes with 4‐Aminoantipyrine Schiff Base Ligand

Cited by 26 publications

References 26 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

4-{(E)-[(2-Hydroxynaphthalen-1-yl)methylidene]amino}-1,5-dimethyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: a new polymorph (β-phase)

Synthesis, Characterization and Antibacterial Activity of Mixed Ligand (HL) Complexes Mn(ll), Co(ll), Ni(ll), Zn(ll), Cd(ll) and Hg(ll) with Azide (N&lt;sub&gt;3&lt;/sub&gt;&lt;sup style=&quot;margin-left:-6px;&quot;&gt;-&lt;/sup&gt;)

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Synthesis, Characterization and Antibacterial Activity of Mixed Ligand (HL) Complexes Mn(ll), Co(ll), Ni(ll), Zn(ll), Cd(ll) and Hg(ll) with Azide (N<sub>3</sub><sup style="margin-left:-6px;">-</sup>)