Synthesis, spectroscopic characterization and antimicrobial studies of some metal complexes with 2-acetylpyridine phenoxyacetyl hydrazone (HAPPA)

Bekheit, M. M.; El-Shobaky, A.R.; Allah, Mohamed T.Gad

doi:10.1016/j.arabjc.2013.11.048

Cited by 9 publications

(5 citation statements)

References 44 publications

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“…The sharp azomethine >C=N‐ bands at about 1630 cm −1 in both the ligands shifted to lower frequencies by about 25–30 cm −1 in all the complexes, confirming the formation of azine group and coordination through one of its nitrogens . The bands at 1588 and 1591 cm −1 assigned to aromatic pyridine C=N absorptions in both the ligands shift to a lower frequency by 10–15 cm −1 in all the complexes, suggesting complexation through this nitrogen . Hence, the IR spectra support the behaviour of both the ligands as tridentate; utilizing pyridine‐N, azine‐N and diimino enolate‐O as donor sites.…”

Section: Resultssupporting

confidence: 61%

“…[35] The bands at 1588 and 1591 cm −1 assigned to aromatic pyridine C=N absorptions in both the ligands shift to a lower frequency by 10-15 cm −1 in all the complexes, suggesting complexation through this nitrogen. [36] Hence, the IR spectra support the behaviour of both the ligands as tridentate; utilizing pyridine-N, azine-N and diimino enolate-O as donor sites. The spectra are rather complex in the region below 500 cm −1 , where the various M-L bond stretching vibrations are often found in combination with other bands (the IR spectra of ligand precursor 2, ligands and their complexes are provided in the Supporting information).…”

Section: Infrared Spectral Studiesmentioning

confidence: 54%

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Copper (II) complexes of 3,5‐di‐tert‐butyl‐2‐hydroxybenzoylhydrazones of 2‐formylpyridine and 2‐acetylpyridine, with tautomeric azine‐scaffold‐based architecture: Synthesis, crystal structures, the effect of counteranions on complexation, and their anti‐microbial and anti‐tuberculosis evaluation

Hegde

Netalkar

Revankar

2019

Applied Organom Chemis

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A series of air‐ and moisture‐stable copper (II) complexes of 3,5‐di‐tert‐butyl‐2‐hydroxy‐N′‐(pyridin‐2‐ylmethylene)benzohydrazide (L1H) and 3,5‐di‐tert‐butyl‐2‐hydroxy‐N′‐(1‐(pyridin‐2‐yl)ethylidene)benzohydrazide (L2H) were synthesized. The two newly designed hydrazone Schiff base ligands with the tautomeric azine‐scaffold involving N, N and O ligating architecture were derived from the condensation of 3,5‐di‐tert‐butyl‐2‐hydroxybenzoylhydrazide with 2‐formylpyridine and 2‐acetylpyridine, respectively. The resultant ligands and their copper complexes were characterized using various spectro‐analytical techniques, like infrared (IR), 1H‐NMR, 13C‐NMR, electron paramagnetic resonance, electronic spectroscopy, thermogravimetric analysis and conductance measurements. The interesting inter‐convertible E/Z geometrical isomeric forms of the ligand L1H was established by NMR and IR spectra. In addition, the molecular structures of L2H, C3 and C4 were unambiguously established using the single‐crystal X‐ray diffraction technique. The dichlorido‐bridged dinuclear square pyramidal complexes, with the [Cu2(μ‐Cl)2L2] type of core units, were resulted for the complexes C1 and C3, whereas z‐in compressed mononuclear 1:2 (M:L) octahedral complex geometries resulted for C2, C4 and the rest of the complexes even when various copper (II) precursor salts with different counteranions were used. The ligands and their complexes were investigated for the anti‐microbial activities against gram‐positive and gram‐negative bacteria. The ligand L2H and its complexes C3 and C4 exhibited better anti‐tuberculosis activity than the controls.

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Section: Resultssupporting

confidence: 61%

Section: Infrared Spectral Studiesmentioning

confidence: 54%

Copper (II) complexes of 3,5‐di‐tert‐butyl‐2‐hydroxybenzoylhydrazones of 2‐formylpyridine and 2‐acetylpyridine, with tautomeric azine‐scaffold‐based architecture: Synthesis, crystal structures, the effect of counteranions on complexation, and their anti‐microbial and anti‐tuberculosis evaluation

Hegde

Netalkar

Revankar

2019

Applied Organom Chemis

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“…In particular, 2-acetylpyridine hydrazone derivatives of benzothiazole exhibit a potent toxic effect on lymphomas, leukemias, and breast tumors. , Also, Cu(II) complexes are more potent against rheumatoid arthritis and ulcers due to their role as acidic anti-inflammatory supplementary agents in gastrointestinal damage . Moreover, VO(II) complexes showed a very similar strength of activity to standard drugs such as ciprofloxacin (an antibacterial drug) and clotrimazole (an antifungal drug) .…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization, Cyclic Voltammetry, Biological Investigations, MOE, and Gaussian Calculations of VO(II), Cu(II), and Cd(II) Heteroleptic Complexes

et al. 2023

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A novel hydrazone ligand (o-H2BMP) N-(benzo[d]thiazol-2-yl)-3-oxo-3-(2-(1-(pyridin-2-yl)ethylidene)hydrazinyl)propanamide alongside its Cu(II), Cd(II), and VO(II) complexes were prepared and structurally characterized via various spectroscopic analyses (Fourier transform infrared spectroscopy, UV–visible spectroscopy, 1H/13C NMR spectroscopy, liquid chromatography coupled to mass spectrometry, and electron paramagnetic resonance spectroscopy) as well as by elemental analysis, thermal gravimetry analysis/differential thermal analysis, and magnetic moment measurements. Powder X-ray diffraction analysis was also performed for the free ligand and its metal complexes to determine the crystallographic structures and atomic spacing. It also provided information on unit cell dimensions and the average crystallite size. Furthermore, geometric optimization and computational studies were carried out by applying Gaussian (09) software based on density-functional theory coupled with the B3LYP functional and LANL2DZ/6-31+G(d,p) mixed basis set to evaluate some distinct features such as molecular electrostatic potential, E HOMO, and E LUMO. Moreover, electrochemical measurements were performed for Cu(II) in the absence/presence of the chelating agent to predict the effect of complexation interaction in the solution state study. As part of the biological examination, antioxidant and antimicrobial assays were conducted for each compound individually, in addition to cytotoxicity evaluations via MTT assays for all isolated complexes compared to the corresponding metal salts. The MOE (molecular operating environment) approach was also applied to model the interface between the isolated compounds and proteins that were expressed in breast cancer at the atomic level.

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“…Some complexes of N,N′-bis[2-hydroxynaphthylidene]/ [2-methoxybenzylidene] amino]oxamides with Cu(II), Ni(II) and Pd(II) have been reported elsewhere [8][9][10], and this study is an expansion of the past work. In terms of biological activity, hydrazones including oxalic dihydrazone and their complexes offer a wide scope of pharmacological applications as antitumoral, antiviral and antimicrobial agents [8,[11][12][13]. Metal complexes obtained from arylhydrazones are helpful in the pharmaceutical field [14] and act as enzyme inhibitors.…”

Section: Introductionmentioning

confidence: 99%

N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells

Ahmed

2020

Open Chemistry

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AbstractManganese(ii) complexes of oxalic dihydrazones {N,N′-bis[2-hydroxynaphthylidene]amino]oxamide (BHO) and N,N′-bis[2-methoxybenzylidene]amino]oxamide (BMO)} have been synthesized by a general methodology. Hydrazone ligands (BHO and BMO) were obtained by the condensation of oxalic dihydrazide with 2-hydroxynaphthalene-1-carbaldehyde and 2-methoxybenzaldehyde. From the data obtained from the spectral (mass, IR, 1H-NMR, UV-Vis, ESR), magnetic and thermal measurements in addition to the elemental analyses (CHNM), the structures of ligands and their complexes have been determined. The scanning electron microscope (SEM) was used to characterize the morphology of the complex surface. The ligands coordinated with the metal center in a bi-dentate way forming binuclear Mn–BHO and mononuclear Mn–BMO complexes. The manganese complexes are proposed to have octahedral stereochemistry. The ligands and manganese(ii) complexes have been assessed for their antibacterial and antileukemia activities. The proliferation hindrance for the free ligands was enhanced upon coordination with the manganese(ii) ions.

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Synthesis, spectroscopic characterization and antimicrobial studies of some metal complexes with 2-acetylpyridine phenoxyacetyl hydrazone (HAPPA)

Cited by 9 publications

References 44 publications

Spectroscopic Characterization, Cyclic Voltammetry, Biological Investigations, MOE, and Gaussian Calculations of VO(II), Cu(II), and Cd(II) Heteroleptic Complexes

N,N′-Bis[2-hydroxynaphthylidene]/[2-methoxybenzylidene]amino]oxamides and their divalent manganese complexes: Isolation, spectral characterization, morphology, antibacterial and cytotoxicity against leukemia cells

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