Synthesis and X-ray crystal structures of three new nickel(II) complexes of benzoylhydrazones: Catalytic applications in the synthesis of 2-arylbenzoxazoles

Layek, Samar; Agrahari, Bhumika; Kumar, Akash; Dege, Necmi; Pathak, Devendra Deo

doi:10.1016/j.ica.2019.119222

Cited by 15 publications

(10 citation statements)

References 87 publications

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“…As seen in these complexes, the tensile frequency of the C=N vibration shifts to lower frequencies (i.e., from 1595, 1591 cm −1 in ligands to 1581, 1585 cm −1 in the studied complexes, ν(C=N) it was shifted to lower wavenumber), which approves the coordination of the nitrogen of the azomethine ligand for the metal center. [ 45,51,66,67 ] The band ν(C=O) of the complexes relative to ligands was shifted to lower wavenumber by 35, 30 cm −1 , respectively. A prominent band is observed at 1271, 1269 cm −1 in the spectra of the ligands that can be due to phenolic and naphtolic C‐O vibration.…”

Section: Resultsmentioning

confidence: 99%

“…[47][48][49] Limited crystalline structures of the 4-amino-antipyrine derivatives have been reported. [44,[50][51][52][53][54][55][56] This report documents the first structurally characterized the Cu (II) complex with the 4-([5-bromo-2-hydroxybenzyl]amino)-1,5-dimethyl-2phenyl-1H-pyrazol-3(2H)-one (H 2 L 1 ) and the Ni (II) complex with the 4-([2-hydroxynaphthyl]amino)-1,-5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one (H 2 L 2 ) coordination with 4-amino-antipyrine based ligands (Scheme 1), the purpose of this manuscript is to study various structural features, spectroscopy, and electronics, by modeling density function theory (DFT), molecular electrostatic potential (MEP), atoms in molecules (AIM), and a Monte Carlo adsorption locator, that facilitate and develop the applications of these compounds. In addition, using Hirshfeld analysis, different intermolecular interactions in the crystal structures of the complexes are investigated.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Parvarinezhad

Salehi

Malekshah

et al. 2022

Applied Organom Chemis

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Metal (II) complexes of Cu (II) (1), and Ni (II) (2) with Schiff base derived from 4‐amino‐antipyrine were synthesized. These complexes were fully characterized by FTIR, and UV–Vis spectroscopies, crystallography, and cyclic voltammetry. Crystal structures of these two complexes were mononuclear. Furthermore, complex Cu (II) (1), of [CuII(H2L1)(NO3)] composition, is 4‐coordinated in a square‐planar environment. Complex Ni (II) (2) is six‐coordinated in an octahedral geometry and can be described as [NiII (H2L2)2]; this crystal structure additionally contains solvent—DMSO molecule. The experimental structural models are interpreted by Hirshfeld surface analysis, density functional theory calculations, Molecular Electrostatic Potential, and the atoms in molecules method. Density functional theory calculations support all experimental results, as well as predict the correct structure of complexes. In addition, the types of interactions in the structure of the complexes were identified by Hirshfeld surface analysis, and molecular electrostatic potential was used to confirm the formation of these interactions, and the results of these studies are consistent. Then the theory of atom in molecule was performed, which predicts the type of interaction of the ligand metal non‐covalently with ionic nature. To determine the mechanism of adsorption of complexes on chitosan, a Monte Carlo adsorption locator was utilized. The adsorption process of complex [CuII (H2L1)NO3]and [NiII(H2L2)2(C2H6SO)] in the aqueous phase on CS was calculated by Monte Carlo adsorption locator. The results showed complex [NiII(H2L2)2(C2H6SO)] had a high binding efficiency on CS compared with complex [CuII (H2L1)NO3]. Moreover, the anticancer effects of ligands and complexes toward MTT assay against SW480 cancer cell lines were investigated. The biological activity results illustrate that the ligands and complexes have anticancer activity. Molecular docking studies were also carried out for both complexes to find their binding affinity with protein B‐cell lymphorna (BCL‐2, PDB ID: 4LXD).

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Parvarinezhad

Salehi

Malekshah

et al. 2022

Applied Organom Chemis

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“…GC-MS (EI, 70 eV) m/z: 51, 63, 77, 92, 103, 115, 139, 167, 195. 2-(4-tert-Butylphenyl)benzoxazole (3b) (Layek et al, 2020;Sirgamalla et al, 2020) White solid, mp ¼ 107-108 C 1 H NMR (500 MHz, CDCl 3 ): δ ¼ 8.19 (dt, J ¼ 2.0 Hz, 9.0 Hz, 2H), 7.78-7.76 (m, 1H), 7.59-7.57 (m, 1H), 7.55 (dt, J ¼ 2.0 Hz, 9.0 Hz, 2H), 7. 35-7.34 (m, 2H), 1.38 (s, 9H).…”

Section: General Procedures For the Synthesis Of Benzoxazolementioning

confidence: 99%

“…Azoles scaffolds have been associated with biological activities such as antitumor, antihypertensive, anti-histaminic, and antimicrobial activities ( Figure 1 ) ( Aiello et al., 2008 ; Boyer et al., 2011 ; Daletos et al., 2014 ; He et al., 2017 ; Johnson et al., 2008 ; Ko et al., 2001 ; Leventhal et al., 2006 ; Mishra et al., 2019 ; Oksuzoglu et al., 2008 ; Sun et al., 2004 ; Wang et al., 2014 ). The synthesis of benzoxazoles has been studied extensively via different pathways, including (a) cyclization of 2-aminophenols with β -diketones ( Mayo et al., 2014 ; Miao et al., 2019 ), carboxylic acids ( Dev et al., 2016 ; Yuan et al., 2018 ), aldehydes ( Layek et al., 2020 ; Matloubi Moghaddam et al., 2006 ; Sirgamalla et al., 2020 ), acyl chloride ( Tian et al., 2019 ; Zheng et al., 2019 ), isocyanides ( Akbay et al., 2003 ), alcohols ( Doan et al., 2019 ; Kaldhi et al., 2019 ), (b) oxidative intramolecular C–O coupling, (c) C–H arylation reaction, and (d) oxidative cyclization of phenolic Schiff base ( Chang et al., 2002 ). However, the condensation and aromatization of o -aminophenol was the most popular method for the synthesis of benzoxazoles.…”

Section: Introductionmentioning

confidence: 99%

A green approach for the synthesis of 2-substituted benzoxazoles and benzothiazoles via coupling/cyclization reactions

Nguyen

Pham

et al. 2021

Heliyon

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“…[27] In addition to its biological relevance, hydrazonic chelators play a vital role as potent corrosion inhibitors [28][29][30][31] and as catalyst in several reactions. [31][32][33][34][35] Recently, hydrazonic ligands were acted as a good corrosion inhibitors to safeguard the metals and alloys as steel. [36] As a result of the exciting bioeffect of hydrazonic chelators and in continuance of our earlier researches, on the designing of bioeffective metal complexes.…”

Section: Introductionmentioning

confidence: 99%

Structure investigation, density functional theory, and biostudy of synthesized dihydrazone incorporating isatin moiety and its homo‐bimetallic complexes

Shakdofa

Saleem

Shakdofa

2021

Applied Organom Chemis

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Seven homo-bimetallic complexes derived from 3-(-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene)hydrazono)indolin-2-one with Fe 3+ , Co 2+ , Cu 2+ , and UO 2 2+ have been prepared and structurally investigated using elemental and thermo-gravimetric analyses and spectral, magnetic, and molar conductivity measurements. This structural investigation leads us to conclude that the bis-hydrazone has behaved as neutral tetradentate chelator chelated to the Fe 3+ , Co 2+ , Cu 2+ , and UO 2 2+ ions via the carbonyl and azomethine groups adopting distorted octahedral structure for Fe 3+ , Co 2+ , and Cu 2+ complexes (2-5), whereas the Cu 2+ complexes (6-7) have square planar structures. The structural characterization of bis-hydrazone and its chelated compounds has been supported by density functional theory calculations. The optimized geometry, global reactivity descriptors, and lowest unoccupied molecular orbital (LUMO) and highest occupied molecular orbital (HOMO) of the molecules have been calculated in accordance with the density functional theory (DFT)-Beckee3eLeeeYangeParr (B3LYP) technique and 6e311G(d,p) basis set. The molecular electrostatic potential image was also drawn by the DFT-B3LYP technique and 6e311G(d,p) basis set to envision the charge distribution and chemical reactivity on the molecules. The bioeffect of bis-hydrazone and its chelated compounds was assessed against bacterial strains Bacillus subtilis, Escherichia coli, as well as fungal strains Canadian albicans and Aspergillus niger. The observed data imply encouraging bioeffect of some of these complexes in comparing with the free bis-hydrazone or amphotericin B (AmB) against all fungal C. albicans and A. niger.

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Synthesis and X-ray crystal structures of three new nickel(II) complexes of benzoylhydrazones: Catalytic applications in the synthesis of 2-arylbenzoxazoles

Cited by 15 publications

References 87 publications

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

Synthesis, characterization, spectral studies two new transition metal complexes derived from pyrazolone by theoretical studies, and investigate anti‐proliferative activity

A green approach for the synthesis of 2-substituted benzoxazoles and benzothiazoles via coupling/cyclization reactions

Structure investigation, density functional theory, and biostudy of synthesized dihydrazone incorporating isatin moiety and its homo‐bimetallic complexes

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