Mono- and binuclear copper(II) complexes of new hydrazone ligands derived from 4,6-diacetylresorcinol: Synthesis, spectral studies and antimicrobial activity

Shebl, Magdy; El-ghamry, Mosad A.; Khalil, Saied M. E.; Kishk, Mona A.A.

doi:10.1016/j.saa.2014.02.014

Cited by 84 publications

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“…The complexes displayed a strong band in the range 3217– 3430 cm −1 that may be attributed to ν(NH) and/ or ν(OH) of the non‐coordinated or coordinated water and/ or ethanol molecules associated with the complexes. The band assigned to the azomethine (C=N) group, observed at 1660 cm −1 in the free ligand, was shifted to lower a wave number in the complexes (1576– 1638 cm −1 ), pointing to the involvement of the azomethine N in complex formation . Moreover, the two bands at 1550 and 1449 cm −1 , attributed to ν(C=N) and ν(N=N) of the triazine moiety, respectively, were shifted to lower wave number (1513– 1539 and 1424– 1431 cm −1 ) in all complexes, pointing to the involvement of the triazinic N in complex formation .…”

Section: Resultsmentioning

confidence: 94%

“…The band assigned to the azomethine (C=N) group, observed at 1660 cm −1 in the free ligand, was shifted to lower a wave number in the complexes (1576– 1638 cm −1 ), pointing to the involvement of the azomethine N in complex formation . Moreover, the two bands at 1550 and 1449 cm −1 , attributed to ν(C=N) and ν(N=N) of the triazine moiety, respectively, were shifted to lower wave number (1513– 1539 and 1424– 1431 cm −1 ) in all complexes, pointing to the involvement of the triazinic N in complex formation . In complexes 1 , 3 , and 5 , new bands were detected between 1358– 1381 and 802– 824 cm −1 , which may be due to the monodentate nitrate group .…”

Section: Resultsmentioning

confidence: 94%

“…Triazine‐based ligands have attracted special interest as a result of the importance of these heterocyclic compounds and their various applications, including biological, pharmaceutical, and industrial applications.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Samy

2020

Applied Organom Chemis

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New mononuclear Fe (III), Cu (II), Ag (I), ZrO ( IV) and UO2(VI) complexes were synthesized by the reaction of metal ions with (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime. The structures of the metal complexes were characterized using analytical, spectral (infrared, electronic, 1H NMR, electron spin resonance (ESR), and mass), magnetic moment, molar conductance, thermal gravimetric analysis, and powder X‐ray diffraction (XRD) measurements. All complexes have octahedral geometries except the Cu (II) complex, which has square planar geometry, and the UO2(VI) complex, in which the coordination number is seven. The ligand acts as a (neutral, monoanionic or dianionic) tridentate with N2O coordinating sites: N‐azomethine, N‐triazine, and O‐oxime. Fluorescence spectral studies were carried out in solid state and in dimethylformamide (DMF). The kinetic parameters of the thermal decomposition stages were calculated using Coats–Redfern equations. The morphological structures of the ligand and some complexes were determined using XRD. The molecular orbital calculations were carried out for the ligand and metal complexes using the Hyperchem 7.52 program on the basis of the PM3 level. The antimicrobial activities of the ligand and its complexes were investigated towards the microorganisms S. aureus and B. subtilis as Gram‐positive bacteria, S. typhimurium and E. coli as Gram‐negative bacteria, C. albicans, and A. fumigatus. The ligand and its complexes showed antitumor activity against Hep G‐2 cell lines, where Cu (II) and Ag (I) complexes seem to be promising as they showed IC50 values that are lower than and comparable to that of the antitumor drug doxorubicin.

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Section: Resultsmentioning

confidence: 94%

Section: Resultsmentioning

confidence: 94%

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Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Samy

2020

Applied Organom Chemis

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“…The FT‐IR spectral data of the ligand (Table ) show four characteristic absorption bands at 3427, 1711, 1652 and 1620 cm −1 . The first two bands may be assigned to ν(NH) and ν(C&dbond;O) of the isatin moiety, respectively, while the third and fourth bands may be attributed to ν(C&dbond;O) of the chromone moiety and ν(C&dbond;N), respectively . The UV–visible spectral data of the hydrazone ligand in DMF (Table ) display three bands at 267, 407 and 436 nm.…”

Section: Resultsmentioning

confidence: 99%

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

Khalil

Kishk

EL-Mekkawi

et al. 2019

Applied Organom Chemis

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A new dual‐functional Cu(II) complex and its nanohybrid form encapsulated into NaY zeolite cavities were synthesized. The synthesized compounds were characterized using elemental analyses, X‐ray fluorescence, infrared, 1H NMR, electronic, electron spin resonance and mass spectra, powder X‐ray diffraction, surface area and transmission electron microscopy in addition to conductivity and magnetic susceptibility measurements. The encapsulated Cu(II) complex was catalytically tested for degradation of industrial wastewater. The decolorization and mineralization results indicate that the Cu(II) complex encapsulated into zeolite host is an effective heterogeneous catalyst for real industrial wastewater remediation. In addition, both free and encapsulated Cu(II) complexes were tested as anti‐microbial and anti‐tumour agents. The results show that the Cu(II) complex encapsulated into zeolite has a high activity (IC50 = 14.4 μg ml−1). The results of in vivo toxicity experiments indicate that the Cu(II) complex encapsulated into zeolite is a less toxic biocompatible material (LD50 = 1245 mg kg−1). The catalytic properties, cytotoxicity and toxicity of the new nanohybrid Cu(II) complex encapsulated into zeolite make it a promising eco‐friendly and biocompatible material for water remediation and biomedical applications.

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“…Various hydrazones derived from 4,6‐diacetyl resorcinol and their coordination complexes of nickel(II), cobalt(II), copper(II) and zinc(II) have been investigated against gram‐negative ( Salmonella Typhi and Escherichia Coli ), and gram positive ( Bacillus Subtilis and Staphylococcus Aureus ) bacteria, as well as antifungal activity against Candida Albicans, Aspergillus Niger and Cladosporium oxy‐sporum , with positite results . In copper(II) complexes derived from the products of condensation of 4,6‐diacetyl resorcinol with 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine or isatin monohydrazone the antimicrobial activity of the ligands was enhanced by Cu‐chelation …”

Section: Introductionmentioning

confidence: 99%

4,6‐Diacetyl Resorcinol Based Vanadium(V) Complexes: Reactivity and Catalytic Applications

et al. 2019

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Four ONO donor ligands are isolated from the condensation of 4,6‐diacetyl resorcinol with isonicotinoyl hydrazide (H2dar‐inh, I), nicotinoyl hydrazide (H2dar‐nah, II), benzoyl hydrazide (H2dar‐bhz, III), and 2‐furoyl hydrazide (H2dar‐fah, IV) on refluxing in MeOH. The reaction of in situ generated aqueous K[H2VVO4] with ligands I–IV at neutral pH gives complexes [K(H2O)2][VO2(dar‐inh)] (1), [K(H2O)2][VO2(dar‐nah)] (2), [K(H2O)2][VO2(dar‐bhz)] (3), and [K(H2O)2][VO2(dar‐fah)] (4), respectively. The reaction of [VIVO(acac)2] (acac = acetylacetonato) with these ligands (I–IV) under aerobic conditions in methanol yields oxidomethoxidovanadium(V) complexes [VO(OMe)(MeOH)(dar‐inh)] (5), [VO(OMe)(MeOH)(dar‐nah)] (6), [VO(OMe)(MeOH)(dar‐bhz)] (7), and [VO(OMe)(MeOH)(dar‐fah)] (8). All the isolated complexes are characterized by elemental, thermal, electrochemical, and spectroscopic techniques [FTIR, UV/Vis, NMR (1H, 13C and 51 V NMR)], and single‐crystal X‐ray diffraction analysis (for 1, 6, 7, and 8). X‐ray analysis confirms the coordination of the ligands through Ophenolate, Nazomethine, and Oenolate to the metal center. In the molecular structure of [K(H2O)(EtOH)][VVO2(dar‐inh)] (abbreviated as 1a where one molecule of water is replaced by EtOH), water molecules act as bridges between two K+ ions and the complex shows a dimeric structure due to the presence of electrostatic interactions between V=O oxygen atoms with K+ ions. These complexes are active catalysts for the oxidative bromination of thymol in the presence of KBr, HClO4, and H2O2 and give 2‐bromothymol, 4‐bromothymol, and 2,4‐dibromothymol as major products. Complexes 1–4 were also tested as catalysts for the epoxidation of various alkenes (namely styrene, cyclohexene, cis‐cyclooctene, 1‐hexene, 1‐octene, cyclohexenone, and trans‐stilbene) with H2O2 in the presence of NaHCO3 as promoter, giving the corresponding epoxides selectively.

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Mono- and binuclear copper(II) complexes of new hydrazone ligands derived from 4,6-diacetylresorcinol: Synthesis, spectral studies and antimicrobial activity

Cited by 84 publications

References 47 publications

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

Synthesis, spectroscopic, biological, and theoretical studies of new complexes from (E)‐3‐(2‐(5, 6‐ diphenyl‐1,2,4‐ triazin‐3‐ yl)hydrazono)butan‐2‐ one oxime

New less toxic zeolite‐encapsulated Cu(II) complex nanomaterial for dual applications in biomedical field and wastewater remediation

4,6‐Diacetyl Resorcinol Based Vanadium(V) Complexes: Reactivity and Catalytic Applications

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