Novel thiophene-benzothiazole derivative azomethine and amine compounds: Microwave assisted synthesis, spectroscopic characterization, solvent effects on UV–Vis absorption and DFT studies

Ermiş, Emel; Durmuş, Kaan

doi:10.1016/j.molstruc.2020.128354

Cited by 20 publications

(4 citation statements)

References 61 publications

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“…Schiff bases are considered a well-known category of organic components due to their easy synthesis reactions between several primary aromatic amines and carbonyl compounds. [1][2][3][4][5] Also, due to azomethine moiety, their value has increased in the field of coordination chemistry. This is because they have a wide range of biological properties, [6][7][8][9][10][11][12] as they can form stable structures that can increase the biological effects of ligands through their coordination with many transition metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Abdel‐Rahman

Basha

Al–Farhan

et al. 2021

Applied Organom Chemis

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In this study, five novel complexes for Co(II), Ni(II), VO(II), Cr(III), and La(III) ions were synthesized from a tridentate NNO monobasic chelating Schiff base ligand, (Z)-2-((pyridin-2-ylimino)methyl)phenol (HL). Spectral and analytical tools were applied to elucidate the structural compositions of the new compounds. Then, geometry optimization was conducted for all the syntheses by the Gaussian 09 program via the density functional theory method to obtain optimal structures and the most essential parameters. Moreover, the biochemical behaviors of all the syntheses were explored based on the reactivity, which was tested against various cancer cell lines (HepG-2, MCF-7, and HCT-116). The complexes exhibited an interestingly antiproliferative potential against human cancer cell lines, and the cytotoxicities of the new complexes were arranged to follow the order: VOL > CrL > NiL > LaL > CoL > HL. The antioxidant behaviors of the complexes were studied using the DPPH assay, and VOL showed the maximum antioxidant activity, followed by LaL. The antibacterial activities of the HL ligand and its complexes were studied. Moreover, the binding nature of the complexes with calf thymus DNA (CT-DNA) was investigated based on the spectrophotometric absorption titration, viscosity, and gel electrophoresis methods. The binding ability of the complexes with CT-DNA was proposed to be just intercalation or replacement mode. The intrinsic binding constant K b was calculated and arranged based on the following order: VOL (5.2 Â 10 5 ) > CrL (3.6 Â 10 5 ) > NiL (3.3 Â 10 5 ) > LaL (3.0 Â 10 5 ) > CoL (1.12 Â 10 5 ) mol À1 dm À3 . Docking investigations were performed using the receptors of COVID-19's main protease viral protein (PDB ID: 6LU7) and Escherichia coli (gram [-ve] bacteria [PDB ID: 1fj4]).

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Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Abdel‐Rahman

Basha

Al–Farhan

et al. 2021

Applied Organom Chemis

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“…Crystallographic data: Crystals of APP (C 60 H 60 N 9 O 6 P 3 , M = 1096.08) are monoclinic, space group P2 1 /n; at 296 K: a = 8.4373(2), b = 14.9917(3), c = 46.2319(8) Å, β = 94.4940 (10) • , V = 5829.9(2) Å 3 , Z = 4, d calc = 1.249 g cm −3 , µ(MoKα) = 1.60 cm −1 , and F(000) = 2304. The intensities of 66102 reflections were measured with a Bruker Quest D8 CMOS diffractometer (Bruker AXS, Madison, USA) [λ(MoKα) = 0.71073 Å, ω-scans, 2θ < 54 • ], and 12686 independent reflections were used for further refinement.…”

Section: Methodsmentioning

confidence: 99%

“…Azomethines inhibit steel corrosion in hydrochloric [6] and sulfuric [7] acid solutions since they are easily adsorbed at the metal/solution interface. Azomethines with various substituents at nitrogen and carbon atoms are applied in medicine and pharmacology owing to their antimicrobial action, lack of toxicity [8,9], and biological activity [10,11]. Schiff bases with benzothiazole and sulfonate groups inhibit a pancreatic enzyme: lipase; this is important for the treatment of obesity [12].…”

Section: Introductionmentioning

confidence: 99%

Crystallization of Nano-Sized Macromolecules by the Example of Hexakis-[4-{(N-Allylimino)methyl}phenoxy]cyclotriphosphazene

2022

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The synthesized compound was characterized by 31P, 13C, and 1H NMR spectroscopy and MALDI-TOF mass spectroscopy. According to DSC data, the compound was initially crystalline, but the crystal structure was defective. The crystals suitable for X-ray diffraction study were prepared by slow precipitation of the compound from a solution by a vapor of another solvent. A study of the single crystal obtained in this way demonstrated that the phosphazene ring has a flattened chair conformation. It was found that the sphere circumscribed around the compound molecule has a diameter of 2.382 nm.

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“…The imine group (azomethine) of Schiff bases attracted much attention due to widely usage in biological studies and which was use in chemistry (Venkataramana et al, 2010;Yan et al, 2012;Gupta & Goklani, 2017;Ermiş & Durmuş, 2020). Piperazine ring is also an important class of N-heterocyclics having biological activities including antitumor (Xu et al, 2019), antiviral drugs (Hooshmand et al, 2021), antibacterial (Jalagari et al, 2019) and antifungal etc (Suryavanshi & Rathore, 2017) and pharmaceutical applications (Ullh et al, 2022).…”

Section: Introductionmentioning

confidence: 99%

Design, DFT Calculations and Antimicrobial Activity of New Synthesized Piperazine Derivative

MUHAMMET>

2023

Gazi University Journal of Science Part A: Engineering and Innovation

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The title compound (2,2'-(piperazine-1,4-diyl)bis(N'-((E)-5-chloro-2-hydroxybenzylidene) acetohydrazide) (5-ClPAH) was synthesized by reacting 1,4-Piperazinediacetic acid, 1,4-dihydrazide and 5 -Chloro-2-hydroxybenzaldehyde. Mass spectrometry, 1H, 13C-NMR, IR results of the synthesized compound were examined. Many information about physical and chemical properties of 5-ClPAH can be obtained by theoretical calculations. Density functional theory (DFT) is widely used theoretical method for predicting of chemical structures. The structure was optimized using DFT/6311G method with GAUSSIAN09. Frontier Molecular Orbitls (HOMO and LUMO) energies were calculated. Global reactivity descriptors and also electrophilic and nucleophilic regions were defined by molecular electrostatic potential surface. Antibacterial and fungal activity were evaluated.

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Novel thiophene-benzothiazole derivative azomethine and amine compounds: Microwave assisted synthesis, spectroscopic characterization, solvent effects on UV–Vis absorption and DFT studies

Cited by 20 publications

References 61 publications

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Synthesis, characterization, potential antimicrobial, antioxidant, anticancer, DNA binding, and molecular docking activities and DFT on novel Co(II), Ni(II), VO(II), Cr(III), and La(III) Schiff base complexes

Crystallization of Nano-Sized Macromolecules by the Example of Hexakis-[4-{(N-Allylimino)methyl}phenoxy]cyclotriphosphazene

Design, DFT Calculations and Antimicrobial Activity of New Synthesized Piperazine Derivative

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