Synthesis, spectroscopic characterization, crystal structure, DFT studies and biological activities of new hydrazone derivative: 1-(2,5-bis((E)-4-isopropylbenzylidene)cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine

Saouli, Saliha; Selatnia, Ilhem; Zouchoune, Bachir; Sid, Assia; Zendaoui, Saber Mustapha; Bensouici, Chawki; Bendeif, El‐Eulmi

doi:10.1016/j.molstruc.2020.128203

Cited by 26 publications

(8 citation statements)

References 76 publications

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“…It is worthnoting that the highest global electrophilicity corresponds to the mixture of cinnamic aldehyd with hesperidin (7.48 eV) followed by that of ascorbic acid with cinnamic aldehyd (6.28 eV), which match well with the smallest chemical hardness of 1.34 eV for the former and 1.76 eV for the latter matching well with the highest absolute value of chemical potential (4.61 eV). These findings are comparable to those for our recent work [ 50 ] and suggest high biological activities, because the electrophilicity value enhances with enhancement chemical and biological activities. However, the mixture of ascorbic acid and hesperidin does not enhance significantly the electropholicity predicting the maintenance of biological activities like as before the mixing.…”

Section: Molecular Propertiessupporting

confidence: 91%

How the ascorbic acid and hesperidin do improve the biological activities of the cinnamon: theoretical investigation

Zouchoune

2020

Struct Chem

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DFT/B3LYP calculations have been performed on series of molecules of natural products containing cinnamon and citrus, namely, cinnamic aldehyd, ascorbic acid and hesperidin. This theoretical investigation predicts the biological activities of mixtures between cinnamon and ascorbic acid and between cinnamon and hesperidin based on already proven values for these molecules. The strength of the intermolecular interactions is evaluated in term of energy decomposition of the total interaction energy Δ E int between molecules, which are mainly governed by electrostatic interactions. The HOMO–LUMO gaps explain that the possible charge transfer interactions that take place within the molecules are responsible for the molecular reactivity of the studied molecules. The chemical hardness, the chemical potential and the electrophilicity indexes are good indicators for biological activities showing their improvement to that of cinnamon itself. The mixture of hesperidin and cinnamon could be an excellent blood thinner with the regard to its polarity’s enhancement.

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Section: Molecular Propertiessupporting

confidence: 91%

How the ascorbic acid and hesperidin do improve the biological activities of the cinnamon: theoretical investigation

Zouchoune

2020

Struct Chem

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“…[ 62 ] The HOMO orbit is the electron‐filled orbit with the highest energy, the least bound, and the most likely to lose electrons; the LUMO orbit is the unfilled electron orbit with the lowest energy, which is easy to accept electrons. [ 63 ] Therefore, the HOMO orbit determines the electronic gain and loss and transfer ability of molecules and determines the important chemical properties such as the orientation of intermolecular reactions. [ 64 ] The difference in energy and energy level is important for studying the chemical properties of molecules.…”

Section: Resultsmentioning

confidence: 99%

Investigation of mononuclear, dinuclear, and trinuclear transition metal (II) complexes derived from an asymmetric Salamo‐based ligand possessing three different coordination modes

Bian

Wang

et al. 2020

Applied Organom Chemis

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A new asymmetric Salamo-based ligand H 2 L was synthesized using 3-tert-butyl-salicylaldehyde and 6-methoxy-2-[O-(1-ethyloxyamide)]-oxime-1-phenol. By adjusting the ratio of the ligand H 2 L and Cu (II), Co (II), and Ni (II) ions, mononuclear, dinuclear, and trinuclear transition metal (II) complexes, [Cu(L)], [{Co(L)} 2 ], and [{Ni(L)(CH 3 COO)(CH 3 CH 2 OH)} 2 Ni] with the ligand H 2 L possessing completely different coordination modes were obtained, respectively. The optical spectra of ligand H 2 L and its Cu (II), Co (II) and Ni (II) complexes were investigated. The Cu (II) complex is a mononuclear structure, and the Cu (II) atom is tetracoordinated to form a planar quadrilateral structure. The Co (II) complex is dinuclear, and the two Co (II) atoms are pentacoordinated and have coordination geometries of distorted triangular bipyramid. The Ni (II) complex is a trinuclear structure, and the terminal and central Ni (II) atoms are all hexacoordinated, forming distorted octahedral geometries. Furthermore, optical properties including UV-Vis, IR, and fluorescence of the Cu (II), Co (II), and Ni (II) complexes were investigated. Finally, the antibacterial activities of the Cu (II), Co (II), and Ni (II) complexes were explored. According to the experimental results, the inhibitory effect was found to be enhanced with increasing concentrations of the Cu (II), Co (II), and Ni (II) complexes.

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“…Based on the computed global and local chemical descriptors of density functional theory (DFT) study, we will attempt to compare and to predict the evolution of the possible biological activities for the aforementioned natural products. The chemical descriptors, namely the HOMO-LUMO gaps, chemical potential, chemical hardness [53,54], and electrophilicity indexes [55][56][57], are global reactivity descriptors which have been calculated by means of DFT/B3LYP method to predict biological activities [58][59][60] with high performance in predicting global chemical reactivity tendencies. The electrophilicity is a considerable index of reactivity permitting a quantitative classification of the electrophilic nature of a molecule [58][59][60].…”

Section: Introductionmentioning

confidence: 99%

Molecular structures, chemical descriptors, and pancreatic lipase (1LPB) inhibition by natural products: a DFT investigation and molecular docking prediction

Allal

Nemdili²,

Zerizer

et al. 2023

Struct Chem

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Density functional theory (DFT) calculations and molecular docking have been carried out on natural products containing eugenol, gingerol, ascorbic acid, oleurpoein, piperine, hesperidin, quercetin, Luteolin, and curcumin in order to predict their biological activities and to analyze their pancreatic lipase inhibition. The biological activity predictions are based on the global and local chemical descriptors, namely, HOMO–LUMO gaps, chemical hardness, chemical potential, electrophilicity, dipole moment, and Fukui functions. Our findings show that the studied compounds can be divided into two groups based on the chemical descriptors; the first group is composed of eugenol, gingerol, ascorbic acid, and oleuropein and the second one is composed of piperine, hesperidin, quercetin, Luteolin, and curcumin depending on the HOMO–LUMO gaps and electrophilicity values predicting best reactivity for the second group than the first one. The frontier orbitals offer a deeper insight concerning the electron donor and electron acceptor capabilities, whereas the local descriptors resulting from Fukui functions put emphasis on the active sites of different candidate ligands. The molecular docking was performed in order to compare and identify the inhibition activity of the natural candidate ligands against pancreatic lipase which were compared to that of synthesized ones. The molecular docking results revealed that the Luteolin compound has the best binding affinity of −8.56 kcal/mol due to their unique molecular structure and the position of -OH aromatic substituents. Supplementary Information The online version contains supplementary material available at 10.1007/s11224-023-02176-2.

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Synthesis, spectroscopic characterization, crystal structure, DFT studies and biological activities of new hydrazone derivative: 1-(2,5-bis((E)-4-isopropylbenzylidene)cyclopentylidene)-2-(2,4-dinitrophenyl) hydrazine

Cited by 26 publications

References 76 publications

How the ascorbic acid and hesperidin do improve the biological activities of the cinnamon: theoretical investigation

How the ascorbic acid and hesperidin do improve the biological activities of the cinnamon: theoretical investigation

Investigation of mononuclear, dinuclear, and trinuclear transition metal (II) complexes derived from an asymmetric Salamo‐based ligand possessing three different coordination modes

Molecular structures, chemical descriptors, and pancreatic lipase (1LPB) inhibition by natural products: a DFT investigation and molecular docking prediction

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