Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Tiwari, Dilip Kumar; Basnet, Kanchan; Lamichhane, Janardan; Niraula, Prasodhan; Bhandari, Sunil; Yadav, Pravesh

doi:10.14233/ajchem.2016.20127

Cited by 15 publications

(9 citation statements)

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“…The 1 H NMR spectrum of the ligand presents a singlet at δ 12.60 ppm corresponding to the azide N-H proton and the singlet at δ 8.63 ppm is attributed to the thioamide S=C-NH2 proton. These results are similar to the chemical shifts reported for imidazole-2-carbaldehyde N-(4)-substituted thiosemicarbazones, which exist in the E isomeric form [15]. On the other hand, the resonance lines of the protons in the multiplet, corresponding to the aromatic ring, were observed at δ 7.31-7.43 ppm.…”

Section: Nmr Spectral Analysissupporting

confidence: 88%

“…These vibration modes suggest the involvement of the sulfur atom in coordination, thus confirming the tridentate nature of the 2-(phenyl(pyridin-2-yl)methylene)hydrazine-1-carbothioamide ligand in the complexes [29,33]. This is further supported by the appearance of new bands at 484-580 and 410-415 cm -1 in the far-infrared region, assigned to ν(M-N), and ν(M-S), respecttively [15]. Furthermore, infrared spectra of Cu(II) complexes show a new absorption band around 1037-1235 cm -1 , initially absent in the ligand spectrum, that is assigned to the coordination of the nitrate group with the central metal ion [34,35].…”

Section: Infrared Spectroscopymentioning

confidence: 56%

“…Thiosemicarbazones have received a lot of attention due to their structural flexibility, variable binding modes, and ease to form stable chelates with metal ions [10][11][12]. Thiosemicarbazones containing nitrogen atoms have been the subject of extensive study due to their potential industrial and biological applications [13][14][15]. Most tridentate donor ligands have been shown to stabilize metal ion centers, forming strain-free five-or six-membered rings [14].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and biological activity of Cu(II), Ni(II), and Zn(II) complexes of a tridentate heterocyclic Schiff base ligand derived from thiosemicarbazide and 2-benzoylpyridine

et al. 2022

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Ni(II), Cu(II), and Zn(II) complexes of the tridentate heterocyclic ligand, 2-(phenyl(pyridin-2-yl)methylene)hydrazine-1-carbothioamide (HL) have been synthesized and characterized by various spectroscopic techniques and elemental analyses. Infrared spectroscopy shows that the ligand coordinates to the metal ions through the azomethine and pyridine nitrogen atoms as well as the sulfur atom of the thioamide group to form a tridentate chelate system. In vitro screening of metal complexes against four bacterial strains (Staphylococcus aureus (ATCC 43300), Klebsiella pneumoniae (ATCC 700603), Methicillin resistant staphylococcus aureus (ATCC 33591), Shigella flexneri (NR 518)) and four fungal strains (Candida albicans (NR 29444), Candida albicans (NR 29445), Candida albicans (NR 29451), Candida krusei (HM 1122)) indicate that the Cu(II) complex showed good antibacterial activity on Methicillin resistant staphylococcus aureus (ATCC 33591) while the Zn(II) complex showed moderate activity against some of the bacterial and fungi strains. Antioxidant studies reveal that the complexes are more potent than the ligand to eliminate free radicals, with the Ni(II) complex showing the best free radical scavenger.

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Section: Nmr Spectral Analysissupporting

confidence: 88%

Section: Infrared Spectroscopymentioning

confidence: 56%

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, and biological activity of Cu(II), Ni(II), and Zn(II) complexes of a tridentate heterocyclic Schiff base ligand derived from thiosemicarbazide and 2-benzoylpyridine

et al. 2022

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“… 40 Chlorine percentages in the complexes were determined by the reported method of potentiometric titration. 41 …”

Section: Methodsmentioning

confidence: 99%

“…Synthesis of copper(II) chitosan TSCs employed an extensive stirring of an equimolar mixture of chitosan thiosemicarbazone and copper(II) chloride in 1% acetic acid solution for 3 h at 65 °C and pH 6 and recovery of the complex in the dry state after filtration and oven-drying overnight at 40 °C, and this process followed subsidiary modifications , in the method of preparation of copper(II) chitosan complexes . Chlorine percentages in the complexes were determined by the reported method of potentiometric titration …”

Section: Methodsmentioning

confidence: 99%

Pyridine-Based NNS Tridentate Chitosan Thiosemicarbazones and Their Copper(II) Complexes: Synthesis, Characterization, and Anticancer Activity

et al. 2022

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Chitosan-functionalized pyridine-based thiosemicarbazones and their copper(II) complexes have been found to own a substantial antiproliferative activity against the tumorigenic Madin Darby canine kidney (MDCK) and MCF-7 cancer cell lines. In the current study, chitosan oligosaccharide (CS) (87% DDA, M w < 3000 Da) and crab shell chitosan (CCS) (67% DDA, M w 350 kDa) were functionalized as chitosan pyridine-2-thiosemicarbazones and chitosan 2-acetyl pyridine-2-thiosemicarbazones, and their copper(II) complexes were synthesized. The formation of chitosan thiosemicarbazones and their NNS tridentate behavior to give the square planar copper(II) chitosan thiosemicarbazone complexes were established by spectroscopic studies, powder X-ray diffraction, elemental analysis, and magnetic moment measurements. The thermal study showed a marked stability of these derivatives before the outset of chitosan backbone degradation at 200 °C. The colorimetric MTT assay revealed a higher activity of CS thiosemicarbazones, viz., CSTSC series (IC 50 375–381 μg mL –1 in the MDCK cell line and 281–355 μg mL –1 in the MCF-7 cell line) than that of high-molecular-weight CCS thiosemicarbazones, viz., CCSTSC series (IC 50 335–400 μg mL –1 in the MDCK cell line and 365–400 μg mL –1 in the MCF-7 cell line), showing an enhanced activity with a decrease in M w and an increase in DDA of constituent chitosan, a higher activity of both of these series of thiosemicarbazones than that of their native chitosan, viz., CS (IC 50 370 μg mL –1 in the MCF-7 cell line and >400 μg mL –1 in the MDCK cell line) and CCS (IC50 > 400 μg mL –1 in both cell lines), and a higher activity of the Cu-CSTSC complexes (IC 50 322–342 μg mL –1 in the MDCK cell line and 278–352 μg mL –1 in the MCF-7 cell line) and Cu-CCSTSC complexes (IC 50 274–400 μg mL –1 in the MDCK cell line and 231–352 μg mL –1 in the MCF-7 cell line) than that of their respective ligands.

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N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones

Habashi

Marjani

2022

Res Chem Intermed

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Copper Complexes of Imidazole-2-carbaldehyde N(4)-Substituted Thiosemicarbazones: Synthesis, Characterization and Antimicrobial Activity

Cited by 15 publications

References 0 publications

Synthesis, characterization, and biological activity of Cu(II), Ni(II), and Zn(II) complexes of a tridentate heterocyclic Schiff base ligand derived from thiosemicarbazide and 2-benzoylpyridine

Synthesis, characterization, and biological activity of Cu(II), Ni(II), and Zn(II) complexes of a tridentate heterocyclic Schiff base ligand derived from thiosemicarbazide and 2-benzoylpyridine

Pyridine-Based NNS Tridentate Chitosan Thiosemicarbazones and Their Copper(II) Complexes: Synthesis, Characterization, and Anticancer Activity

N-methylpyrrolidine as an effective organocatalyst for the regioselective synthesis of 3-hydroxy-3,5/6-di-aryl-1H-imidazo[1,2-a]imidazol-2(3H)-ones

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