Novel benzildihydrazone based Schiff bases: Syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies

Elmacı, Gökhan; Duyar, Halil; Aydıner, Burcu; Yahaya, Issah; Seferoğlu, Nurgül; Şahin, Ertan; Çelik, Süheyla Pınar; Açık, Leyla; Seferoğlu, Zeynel

doi:10.1016/j.molstruc.2019.01.104

Cited by 17 publications

(11 citation statements)

References 38 publications

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“…Frontier molecular orbitals, HOMO and LUMO, play an important role in the study of chemical reactivity and optical properties . The energy bandgap between HOMO and LUMO is an important parameter for determining the molecular properties such as stability and activity . The calculated HOMO and LUMO energies were found to be −4.88 and −1.48 eV for complex 1 and −3.81 and −3.22 eV for complex 2 .…”

Section: Resultsmentioning

confidence: 99%

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

Sanatkar

Khorshidi

Janczak

2020

Applied Organom Chemis

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Two novel dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N2O2 Schiff base ligand (H2L = N,N′‐bis‐(4‐hydroxysalicylidene)‐1,3‐diaminopropane) were prepared. The structures of the H2L ligand, [4(Zn2L(μ‐O2CCH3)(O2CCH3)(H2O))]⋅4CH3OH⋅3H2O (complex 1) and [Co4L2(μ‐O2CCH3)2(O2CCH3)2]⋅2H2O (complex 2) were unambiguously characterized by elemental analysis, mass spectrometry, Fourier‐transform infrared spectroscopy (FT‐IR), 1H nuclear magnetic resonance (NMR), and UV–Vis spectroscopy. Single crystal X‐ray diffraction studies revealed that two Zn(II) nuclei of 1 were connected through μ‐phenolato and μ‐acetato bridges and had distorted square pyramidal and distorted octahedral coordination geometries. Four Co(II) nuclei of 2, on the contrary, showed a Co4O4 cubane‐like configuration in which Co(II) cations and O atoms were located at alternating corners of a distorted cube. Density functional theory studies at the B3LYP/6–31 G(d) level were carried out to gain an insight into the thermodynamic stability of the complexes. in vitro cytotoxicity of the ligand and the complexes were evaluated using the MTT assay against breast cancer MCF7 cells, melanoma cancer A375 cells, and prostate cancer PC3 cells as representative human cancer cell lines. Complex 1 showed a remarkable activity against A375 and PC3 cancer cell lines. In addition, 1 and 2 were used as precursors to produce zinc and cobalt oxide nanoparticles via pyrolysis technique. The resulting ZnO and Co3O4 nanoparticles were characterized using FT‐IR spectroscopy, UV–Vis diffuse reflectance spectroscopy, powder X‐ray diffraction, and field emission scanning electron microscopy. Then, these nanoparticles were used as heterogeneous catalysts in the oxidation of benzyl alcohol with hydrogen peroxide at room temperature. Both catalysts showed good recyclability with a negligible decrease in their efficiency during four catalytic cycles. The results of theoretical calculations showed that the most stable product was benzaldehyde, which is in good agreement with the obtained experimental results.

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Section: Resultsmentioning

confidence: 99%

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

Sanatkar

Khorshidi

Janczak

2020

Applied Organom Chemis

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“…The 3Cl-Ph-HN-N=C 9 -C 29 =N-NH-Ph-3Cl moieties were found to be in the s-Trans conformation, this positioning has been defined by the contact interactions and steric effects which forced a rotation of the two hydrazone units relative to C9-C29 single bond axis [32] . These two moieties are nearly perpendicular to one another by the dihedral angle N 8 C 9 C 29 N 28 (-80.80°).…”

Section: Resultsmentioning

confidence: 98%

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Tabbiche

Bouchama

Chafai

et al. 2022

Journal of Molecular Structure

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“…The studied (H 4 L) ligand had E HOMO > E LUMO , so it had a high ability for electron donation. The computed energy gap E g is a crucial stability indicator that aids in the identification of a molecule’s chemical reactivity and kinetic stability . The ligand to central metal ion electronic charge transfer increases as the E g drops, making it easier to offer electrons to an acceptor.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Some Novel Nanosized Chelates of Anchoring Bisazo Dye 5-[5-(4,6-Dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione and Their Applications as Antioxidant and Antitumor Agents

2021

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A novel bisazo 5-[5-(4,6-dioxo-2-thioxo-hexahydro-pyrimidin-5ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione (H 4 L) ligand has been synthesized from diazotization coupling between naphthalene-1,5diamine and 2-thiobarbituric acid. Mn(II), Co(II), Ni(II), Cu(II), Zn(II), and Fe(III) chelates were prepared. All prepared compounds were characterized by different techniques. The azo groups did not participate in chelation according to the infrared spectra, whereas the thioamide group did participate. The azo dye ligand coordinated with all metallic ions in a neutral−keto−thiol structure and behaved as a bi-and tridentate moiety. Zinc, manganese, and iron chelates had an octahedral structure, while nickel and cobalt chelates had a tetrahedral structure, but the copper chelate had a square pyramidal geometry. The thermal behavior of all prepared compounds was investigated and thermokinetic parameters were also discussed. X-ray diffraction (XRD) data reflected that Fe(III) and Zn(II) complexes were crystalline while the Cu(II) complex was amorphous. Calcination of the Fe(III) complex at 600 °C yielded a nanosized Fe 2 O 3 crystalline phase, elucidated by XRD and transmission electron microscope. The novel azo dye and some of its chelates were tested against HepG-2. The Fe 2 O 3 nanooxide showed remarkable activity against the HepG-2 cell line rather than its precursor Fe(III) complex. Co(II) had a higher antioxidant activity than the other investigated complexes. In both activities, the Cu(II) complex did not show any activity. Molecular modeling and some theoretical studies were validated, and the experimental results were interpreted.

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Novel benzildihydrazone based Schiff bases: Syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies

Cited by 17 publications

References 38 publications

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Synthesis of Some Novel Nanosized Chelates of Anchoring Bisazo Dye 5-[5-(4,6-Dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione and Their Applications as Antioxidant and Antitumor Agents

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Novel benzildihydrazone based Schiff bases: Syntheses, characterization, thermal properties, theoretical DFT calculations and biological activity studies

Cited by 17 publications

References 38 publications

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N2O2 Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N2O2 Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

New bis hydrazone: Synthesis, X-ray crystal structure, DFT computations, conformational study and in silico study of the inhibition activity of SARS-CoV-2

Synthesis of Some Novel Nanosized Chelates of Anchoring Bisazo Dye 5-[5-(4,6-Dioxo-2-thioxo-hexahydro-pyrimidin-5-ylazo)-naphthalen-1-ylazo]-2-mercapto-1H-pyrimidine-4,6-dione and Their Applications as Antioxidant and Antitumor Agents

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Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation

Dinuclear Zn(II) and tetranuclear Co(II) complexes of a tetradentate N₂O₂ Schiff base ligand: Synthesis, crystal structure, characterization, DFT studies, cytotoxicity evaluation, and catalytic activity toward benzyl alcohol oxidation