New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies

Purtaş, Fatih; Sayın, Koray; Ceyhan, Gökhan; Köse, Muhammet; Kurtoğlu, Mükerrem

doi:10.1016/j.molstruc.2017.02.065

Cited by 28 publications

(13 citation statements)

References 34 publications

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“…Azo dyes have been widely used in various areas, such as textile dyes (1-2), printing systems (2), photoelectronics (3), coloring fibres (4) and optical storage technology. They are also commonly utilised in many biological reactions (5,6) and in analytical chemistry (7)(8). Schiff bases are also an important class of organic compounds that exhibit a broad range of biological activities, including antibacterial (9), antifungal (9), antiproliferative (8), anti-inflammatory (4), antimalarial (8), antipyretic (8) and antiviral (5) properties (6,10).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Özkınalı¹,

Çavuş²,

Sakin³

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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In this study, azo dyes containing an imine group were synthesised by coupling phydroxybenzylidene aniline with the diazonium salts of p-toluidine, 4-aminophenol, aniline, pchloroaniline, p-fluoroaniline and p-nitroaniline. The compounds were characterised by melting point, elemental, UV-Vis and IR analyses as well as 1 H-NMR and 13 C-NMR spectroscopies. Moreover, the experimental data were supplemented with density functional theory (DFT) calculations. The experimental data on FT-IR and UV-Vis spectra of the compounds were compared with theoretical results. The DFT calculations were performed to obtain the ground state geometries of the compounds using the B3LYP hybrid functional level with 6-311++g(2d,2p) basis set. Frontier molecular orbital energies, band gap energies and some chemical reactivity parameters, such as chemical hardness and electronegativity, were calculated and compared with experimental values. A significant correlation was observed between the dipole moment and polarities of the solvents and the absorption wavelength of the compounds.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Özkınalı¹,

Çavuş²,

Sakin³

2017

Journal of the Turkish Chemical Society, Section A: Chemistry

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“…The experimental frequency at 964 cm −1 was calculated as 983.8 cm −1 and the corresponding vibration mode of this frequency was labeled as C−Br bond stretching. The experimental frequency at 759, 728 and 682 cm −1 was calculated as 808.9, 742.3 and 709.5 cm −1 , respectively, and this frequency labeled as wagging in hydrogens attached to the aromatic carbon. The similar data were obtained for other compounds.…”

Section: Resultsmentioning

confidence: 99%

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Ceylan

Erkan

Yağlıoğlu

et al. 2020

Chemistry & Biodiversity

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The 2-[2-(2-phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were synthesized from the reactions of 7benzylidenebicyclo[3.2.0]hept-2-en-6-ones with 2-aminobenzenethiol. The antiproliferative activities of 2-[2-(2phenylethenyl)cyclopent-3-en-1-yl]-1,3-benzothiazoles were determined against C6 (rat brain tumor) and HeLa (human cervical carcinoma cells) cell lines using BrdU cell proliferation ELISA assay. Cisplatin and 5-fluorouracil (5-FU) were used as standards. The most active compound was 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl] cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 cell lines with IC 50 = 5.89 μM value (cisplatin, IC 50 = 14.46 μM and 5-FU, IC 50 = 76.74 μM). Furthermore, the most active compound was 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl) ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa cell lines with IC 50 = 3.98 μM (cisplatin, IC 50 = 37.95 μM and 5-FU, IC 50 = 46.32 μM). Additionally, computational studies of related molecules were performed by using B3LYP/6-31G + (d,p) level in the gas phase. Experimental IR and NMR data were compared with the calculated results and were found to be compatible with each other. Molecular electrostatic potential (MEP) maps of the most active 2-{(1S,2S)-2-[(E)-2-(2methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against HeLa and the most active 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole against C6 were investigated, aiming to determine the region that the molecule is biologically active. Biological activities of mentioned molecules were investigated with molecular docking analyses. The appropriate target protein (PDB codes: 1 M17 for the HeLa cells and 1JQH for the C6 cells) was used for 2-{(1S,2S)-2-[(E)-2-(2-methoxyphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole and 2-{(1S,2S)-2-[(E)-2-(4-methylphenyl)ethenyl]cyclopent-3-en-1-yl}-1,3-benzothiazole molecules exhibiting the highest biological activity against HeLa and C6 cells in the docking studies. As a result, it was determined that these molecules are the best candidates for the anticancer drug. Figure 5. Interaction of molecule 5c (pink balls) with protein 1M17 and that of molecule 5e (red balls) with protein 1JQH.1 H-NMR (400 MHz, CDCl 3 ): 8.02 (d, J = 8.2, 1H), 7.87 (d, J = 7.8, 1H), 7.48 (ddd, J = 8.3, 7.2, 1.3, 2H), 7.43-7.31 (m, 4H), 7.06 -6.97 (m, 2H), 6.46 (d, J = 15.8, 1H), 6.22 (dd, J = 15.8, 8.0, 1H), 5.98 -5.92 (m, 1H), 5.82 -5.76 (m, 1H), 3.99 -3.87 (m, 1H), 3.77 (dt, J = 8.8, 7.3, 1H), 3.16 -3.03 (m, 1H), 3.00 -2.89 (m, 1H). 13 C-NMR (101 MHz,

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“…There are several compounds reported containing even more than one azo chromophore per molecule, also linked to heterocyclic systems (Patni & Patni, 2016). The compounds are commonly prepared through a coupling reaction between an arenediazonium salt and typically aromatic data reports phenols or amines, although other substituents such as carboxylates or aldehydes can also be present (Purtas et al, 2017). Besides the wide application of these compounds in both textile and paint industries, the molecular structures of the azo dyes can be modified and tuned to act as ligands in coordination chemistry.…”

Section: Structure Descriptionmentioning

confidence: 99%

Bis{μ-ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}bis[aqua(4-{[4-(ethoxycarbonyl)phenyl]diazenyl}phenolato-κO){ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}potassium]

et al. 2017

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] are connected through a double bridge involving two centrosymmetrically related ethyl-4-(phenylazophenol)benzoate ligands. Each cation is also bound to a further non-bridging ligand, one ethyl-4-(phenylazophenolate)benzoate anion and a water molecule, leading to a distorted fivefold coordination. The two uncharged ligands are almost planar, whereas in the anionic ligand the aromatic systems display a dihedral angle of 21.14 (11). A supramolecular network formed by hydrogen-bonding interactions between phenolate anions, phenol groups and water molecules connects the dimeric species along [001]. Hirshfeld surface calculations revealed the following contributions related to intermolecular interactions: CÁ Á ÁH (24.4%), OÁ Á ÁH (13.2%) and NÁ Á ÁH (7.4%). The azo fragment is disordered over two sets of sites [occupancy ratio 0.824 (15):0.176 (5)].

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New fluorescent azo-Schiff base Cu(II) and Zn(II) metal chelates; spectral, structural, electrochemical, photoluminescence and computational studies

Cited by 28 publications

References 34 publications

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Synthesis, Characterisation and DFT Calculations of Azo-Imine Dyes

Antiproliferative Evaluation of Some 2‐[2‐(2‐Phenylethenyl)‐cyclopent‐3‐en‐1‐yl]‐1,3‐benzothiazoles: DFT and Molecular Docking Study

Bis{μ-ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}bis[aqua(4-{[4-(ethoxycarbonyl)phenyl]diazenyl}phenolato-κO){ethyl 4-[(4-hydroxyphenyl)diazenyl]benzoate-κO}potassium]

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