Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases

Kavitha, P.; Saritha, M.; Reddy, Kotha Laxma

doi:10.1016/j.saa.2012.10.037

Cited by 102 publications

(27 citation statements)

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“…[28]. In the spectra of the complexes, the azomethine proton (CH=N) and 2-H signals are shifted downfield indicating the participation of the former group in coordination [34,35]. In complexes, (3), (4), (5) and (8), the NH signals were absent, indicative of deprotonation of the enolized hydrazone, i.e., fcbh -functions as a mononegative tridentate ligand through pyrone carbonyl oxygen, azomethine nitrogen and deprotonated enolized hydrazone oxygen atoms [31].…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes

Elsayed

Butler

Claude

et al. 2014

Transition Met Chem

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A new Schiff base derived from 3-formylchromone and benzohydrazide (Hfcbh) and its Ni(II), Zn(II), Ru(II), Ru(III), Pd(II), Pt(II) and Ag(I) complexes were synthesized. These compounds were characterized on the basis of physicochemical and spectroscopic methods. Two modes of chelation for Hfcbh are reported: (1) neutral tridentate ligand through the chromone carbonyl oxygen, hydrazonic carbonyl oxygen and azomethine nitrogen atoms and (2) mononegative tridentate ligand via the chromone carbonyl oxygen, hydrazonic deprotonated hydroxy oxygen and azomethine nitrogen atoms. Free Hfcbh and its Ni(II), Zn(II), Ag(I), Pd(II) and Pt(II) complexes have been tested as anticancer agents against the human breast cancer (MDA-MB231) and human ovarian cancer (OVCAR-8) cell lines. The [Ag(fcbh)(PPh 3 )] complex shows the highest efficacy with a mean IC 50 values of 1.0 (MDA-MB231) and 0.87 (OVCAR-8) lM, respectively.

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Section: Resultsmentioning

confidence: 99%

Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes

Elsayed

Butler

Claude

et al. 2014

Transition Met Chem

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“…The aromatic protons appeared as a set of multiplets in the range 7.82-7.58. The SH signal which appears, in the H 2 L is at 3.37 ppm [53][54][55].…”

Section: Ft-ir and 1 H Nmr Spectral Studiesmentioning

confidence: 99%

Theoretical and experimental studies on three new coordination complexes of Co(II), Ni(II), and Cu(II) with 2,4-dichloro-6-{(E)-[(5-chloro-2 sulfanylphenyl)imino]methyl}phenol Schiff base ligand

Kusmariya

Mishra

2015

J Mol Model

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Three mononuclear coordination complexes of Co(II), Ni(II), and Cu(II) have been synthesized from 2,4-dichloro-6-{(E)-[(5-chloro-2-sulfanylphenyl)imino]methyl}phenol ligand (H 2 L) obtained by simple condensation reaction of 3,5-dichloro-2-hydroxybenzaldehyde and 2-amino-4-chlorobenzenethiol and characterized by elemental analysis, spectral (FT-IR, electronic, and (1)H-NMR), molar conductance, thermal, SEM, PXRD, and fluorescence studies. The PXRD analysis and SEM-EDX micrographs show the crystalline nature of complexes. The domain size and the lattice strain of synthesized compounds have been determined according to Williamson-Hall plot. TG of the synthesized complexes illustrates the general decomposition pattern of the complexes. The ligand exhibits an interesting fluorescence property which is suppressed after complex formation. The Co(II) complex adopted a distorted octahedral configuration while Ni(II) and Cu(II) complexes showed square planar geometry around metal center. The geometry optimization, HOMO-LUMO, molecular electrostatic potential map (MEP), and spin density of synthesized compounds have been performed by density functional theory (DFT) method using B3LYP/6-31G and B3LYP/LANL2DZ as basis set. Graphical abstract Three new coordination complexes of Co(II), Ni(II) and Cu(II) with 2,4-dichloro-6-{(E)-[(5-chloro-2 sulfanylphenyl)imino]methyl}phenol Schiff base ligand.

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“…The oxidative properties impact of these free radicals present within the human metabolic system has been of great concern as it is revealed to be the leading cause of most life endangering ailments [15]; as such the need for a closer look at understanding their origin and modes of action amongst other characteristics, which will in turn give room for strategic approach in scavenging them, is most important. Tridentate 3-formyl chromone Schiff bases showed good antioxidant activities against DPPH at different concentrations with as low as 1.27 g/ml IC 50 value compared to standard drug BHT (IC 50 value of 0.67 g/ml) [16]. More recently, Karthik and fellow researchers synthesized a series of Schiff bases with 4-(methylthio)benzaldehydes that have shown to highly scavenge free radicals [17].…”

Section: Introductionmentioning

confidence: 99%

Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies

Idemudia

Okoh

Sadimenko

et al. 2017

Journal of Chemistry

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Phenylhydrazine was reacted with synthesized acylpyrazolone derivatives 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one, to obtain two new azomethine phenylhydrazones, a study in continuation of our probe into the effects of acyl group substitutions on the physicochemical and free radical scavenging properties of acylpyrazolone Schiff bases. The keto imine tautomers of 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Empp-Ph) and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) according to single X-ray crystallography data which precipitated in good yield are reported. Furthermore they have been characterized by elemental analysis, FTIR, 13 C and 1 H NMR, and mass-spectroscopy techniques. Both phenylhydrazone Schiff bases crystallize in a triclinic crystal system, each with a space group of P-1 (number 2) having short intramolecular N3-H3. . .O1 hydrogen interaction between the first hydrazine hydrogen H3 and the pyrazolone oxygen O1. The antioxidant free radical scavenging activities of titled compounds against 2,2-diphenyl-1-picrylhydrazyl (DPPH) showed a positive response almost as good as that of vitamin c under the same conditions, with the propyl substituted 4-propyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazone (Prmpp-Ph) having a stronger activity (calculated IC 50 value of 175.66 g/ml).

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Synthesis, structural characterization, fluorescence, antimicrobial, antioxidant and DNA cleavage studies of Cu(II) complexes of formyl chromone Schiff bases

Cited by 102 publications

References 50 publications

Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes

Synthesis, characterization and anticancer activity of 3-formylchromone benzoylhydrazone metal complexes

Theoretical and experimental studies on three new coordination complexes of Co(II), Ni(II), and Cu(II) with 2,4-dichloro-6-{(E)-[(5-chloro-2 sulfanylphenyl)imino]methyl}phenol Schiff base ligand

Substituted 4-Acyl-5-methyl-2-phenyl-pyrazol-3-one-phenylhydrazones with Antioxidant Properties: X-Ray Crystal and Spectroscopic Studies

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