Synthesis, characterisation and DFT studies of three Schiff bases derived from histamine

Touafri, Lasnouni; Hellal, Abdelkader; Chafaa, Salah; Khelifa, A.; Kadri, A.

doi:10.1016/j.molstruc.2017.08.052

Cited by 38 publications

(16 citation statements)

References 36 publications

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“…The order of electronic chemical potential is L 3 > L 2 > L 1 , the greater the electrochemical potential less stable or more reactive is the compound. From the chemical potential ( χ) and chemical hardness (ω) values, the zwitterionic Schiff bases ( L 2 , L 1 ) are found to be the strongest electrophile whereas L 3 is the strongest nucleophile (Figure ) (Table )

true χ = (I + A) / 2; μ = - (I + A) / 2; η = (I - A) / 2; {S = 1 / (2 η); ω = μ}^{2} / (2 η)

…”

Section: Resultsmentioning

confidence: 99%

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

2018

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A zwitterionic Schiff base, (E)-2-((2-(1-hydroxyethyl)phenyliminio)methyl-6-methoxyphenolate (L 1 ) was prepared and fully characterized by spectral methods. The crystal structure was determined by using single crystal X-ray diffraction study. Inter and intra-molecular interactions in L 1 and similar zwitterionic Schiff bases (L 2 = (E)-2-(((2hydroxyethyl)iminio)phenyl)methyl-5-(prop-2yn-1-yloxy)phenolate and L 3 = (E)-2-(2-hydroxy-3methoxybenzylideneammonio)-3-(1H-imidazol-3-ium-4-yl) propanoate) have been established via topological analysis by considering the presence of (3,-1) bond critical points (BCP) between the interacting atoms using the approach of QTAIM (Quantum Theory of Atoms In Molecules) with the aid of ADF (Amsterdam Density Functional) 2017 package. Furthermore, Hirshfeld 2D fingerprint plots and 3D deformation densities were used to determine the interactions quantitatively. The L 1 -L 3 forms a six-member pseudo cycle via an intramolecular N-H···O hydrogen bond, and the crystal structure is further stabilized by the presence of p···p stacking interactions. The effect of hydrogen bonding interactions of the molecule on infra red frequencies has been studied using DFTB (Density Functional based Tight Binding) method with ADF. The effect of intermolecular interactions of these compounds towards biomolecules was studied by using Auto Dock Vina and QTAIM analysis.

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true χ = (I + A) / 2; μ = - (I + A) / 2; η = (I - A) / 2; {S = 1 / (2 η); ω = μ}^{2} / (2 η)

…”

Section: Resultsmentioning

confidence: 99%

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

2018

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“…The in silico and in vitro studies on indole based SBs have proved their antimicrobial potential [12, 13]. The SAR studies revealed that electron pair present on the nitrogen of the imine group is in sp 2 hybridized orbital and has been responsible for its DNA binding ability, leading to potential biological activities [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Singhal

Khanna

2019

Heliyon

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Novel Schiff bases (SBs) were synthesized by condensation of 2-(1-Amino benzyl) benzimidazole with heterocyclic and aromatic carbonyl compounds. The structural characterization was done using 1H, 13C NMR, FTIR and ES-MS spectroscopic techniques. The in silico pharmacokinetics showed that nearly all compounds obeyed Lipinski rule of 5 with low toxicity and metabolic stability. The global reactivity descriptors were calculated using DFT approach. The molecular docking result of SBs with ct-DNA suggested interaction via groove binding mode. The antibacterial activity was tested against S. aureus and E. coli, indicated significant inhibition than reference drug. The compound 4d gave best results at 50 μg ml−1 concentrations. UV/Vis and Fluorescence spectroscopy tools were used to evaluate ct-DNA binding ability of compounds 4a–e through hypochromic shift. The steady state fluorescence predicted a moderate binding constant of 1.12 × 104 for 4d, indicative of non-intercalative mode.

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“…[23] The absorption spectrum of free ligand (L) consisted of an intense band that appeared at 363 nm attributed to n-π* transition of the azomethine group. [23] The absorption spectrum of free ligand (L) consisted of an intense band that appeared at 363 nm attributed to n-π* transition of the azomethine group.…”

Section: Uv-vis Absorption Studiesmentioning

confidence: 99%

“…The UV-vis absorption studies in the range of 200-700 nm were recorded for the ligand and its metal complex at a concentration of 10 −4 M using dimethylformamide as a solvent. [23] The absorption spectrum of free ligand (L) consisted of an intense band that appeared at 363 nm attributed to n-π* transition of the azomethine group. Another intense band at 270 nm in the higher-energy region of the spectrum of the free ligand was attributed to π-π* transition of benzene rings.…”

Section: Uv-vis Absorption Studiesmentioning

confidence: 99%

Spectroscopic, textural, electrical and magnetic properties of antimicrobial nano Fe(III) Schiff base complex

Mousa

Mahmoud

2019

Applied Organom Chemis

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A novel Schiff base ligand (L) was prepared through condensation of 2,6-diaminopyridine and dibenzoyl methane in a 1:1 ratio. This Schiff base ligand was used for complex formation reaction with Fe(III) chloride. The structures of the ligand and its complex were deduced from elemental analyses, mass spectroscopy, 1 H NMR, IR, UV-Vis, electronic spectra, magnetic moment, molar conductivity measurements, thermogravimetric analyses and X-ray diffraction. The molecular and electronic structures of both ligand and complex were optimized theoretically using density function theory (DFT) method.Moreover, the antimicrobial activities of the prepared compounds were studied and proven against some pathogenic bacteria. The Fe(III) complex had higher biological activity than that of the free ligand. Proceeding from the collected information, the properties of the complex were further investigated. The particle size was determined by dynamic light scattering technique to be 92.59 nm.Textural properties of the nano complex were studied by N 2 adsorption to estimate the specific surface area, pore volume and pore size distribution. The pores in the complex were found in the micropore-mesopore range. Differential scanning calorimetric measurements reveal the existence of four endothermic peaks at 243.8, 308, 339.8 and 380.5 K. Dielectric properties and conductivity were scanned at different frequencies and temperatures. The dielectric constant reaches a peak value of 600 at~390 K, 30 Hz. A crossover from the universal dielectric response to the super linear power law of conductivity was reported for this complex at T ≤ 345 K. Finally, the ACmagnetic susceptibility measurements were carried out in the lowtemperature region. The complex showed paramagnetic behavior with a slight change in the magnitude of its magnetic moment at T = 244 K.

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Synthesis, characterisation and DFT studies of three Schiff bases derived from histamine

Cited by 38 publications

References 36 publications

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

Chemical Reactivity and Quantifying the Intra‐ and Intermolecular Interactions in Zwitterionic Compounds

Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on ct-DNA for novel Schiff bases of 2-(1-aminobenzyl) benzimidazole

Spectroscopic, textural, electrical and magnetic properties of antimicrobial nano Fe(III) Schiff base complex

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