Synthesis, Spectroscopy and X-ray Crystallography Structure of Pyridine 4-Carbaldehyde Semicarbazone Schiff Base Ligand

Mahmoudi, Farzaneh; Farhadi, Saeed; Dusek, Michal; Poupon, Morgane

doi:10.33945/sami/ajca.2020.4.14

Cited by 5 publications

(2 citation statements)

References 27 publications

(46 reference statements)

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“…Compared to the C(1)-C(9)-N(14) angle (~120°) of pyridine-2,6-dicarboxylic dihydrazide [ 35 , 50 , 52 , 56 ], shortening of the angles were observed with an average distance of ~113.67° (C(1)-C(10)-N(14)) in both ligands. However, the increased bond angle (~120.47°) at C(10)-N(14)-N(16) in both L1 and L2, compared to the bond angle of pyridine-2,6-dicarboxylic dihydrazide elucidated the change in hybridization to the azomethine nitrogen N(16) for the attachment of an aromatic substituent.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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Polytopic organic ligands with hydrazone moiety are at the forefront of new drug research among many others due to their unique and versatile functionality and ease of strategic ligand design. Quantum chemical calculations of these polyfunctional ligands can be carried out in silico to determine the thermodynamic parameters. In this study two new tritopic dihydrazide ligands, N’2, N’6-bis[(1E)-1-(thiophen-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L1) and N’2, N’6-bis[(1E)-1-(1H-pyrrol-2-yl) ethylidene] pyridine-2, 6-dicarbohydrazide (L2) were successfully prepared by the condensation reaction of pyridine-2, 6-dicarboxylic hydrazide with 2-acetylthiophene and 2-acetylpyrrole. The FT-IR, 1H, and 13C NMR, as well as mass spectra of both L1 and L2, were recorded and analyzed. Quantum chemical calculations were performed at the DFT/B3LYP/cc-pvdz/6-311+ G (d, p) level of theory to study the molecular geometry, vibrational frequencies, and thermodynamic properties including changes of ∆H, ∆S, and ∆G for both the ligands. The optimized vibrational frequency and (1H and 13C) NMR obtained by B3LYP/cc-pvdz/6-311 + G (d, p) showed good agreement with experimental FT-IR and NMR data. Frontier molecular orbital (FMO) calculations were also conducted to find the HOMO, LUMO, and HOMO–LUMO gaps of the two synthesized compounds. To investigate the biological activities of the ligands, L1 and L2 were tested using in vitro bioassays against some Gram-negative and Gram-positive bacteria and fungus strains. In addition, molecular docking was used to study the molecular behavior of L1 and L2 against tyrosinase from Bacillus megaterium. The outcomes revealed that both L1 and L2 can suppress microbial growth of bacteria and fungi with variable potency. The antibacterial activity results demonstrated the compound L2 to be potentially effective against Bacillus megaterium with inhibition zones of 12 mm while the molecular docking study showed the binding energies for L1 and L2 to be −7.7 and −8.8 kcal mol−1, respectively, with tyrosinase from Bacillus megaterium.‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬

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Section: Resultsmentioning

confidence: 99%

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

et al. 2022

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“…Table 4 summarizes the magnetic sensitivity as well as the ratio (1:1). The band mentioned at 3306.1 cm -1 , which is related to the stretching υ (NH), and υ (C=O) stretching at 1645.33 cm -1 , which is attrition, may be seen in the infrared spectra of the ligand [23]. The complexes appear to dissipate and the band (NH) vanishes due to coordination and frequency shifts (C=O) and the other ranges are summarized in Table 5.…”

Section: Results and Dissectionsmentioning

confidence: 98%

Untitled

2022

J. Med. Chem. Sci.

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By condensation reaction between P-amino benzoic acid and ethanol in the presence of concentrated H2SO4 to produce ethyl 4-aminobenzoate, which was then converted into N, N'-(1,2-phenylene) bis(4-aminobenzamide) type [H2L] (N2O2) product by direct interaction between the two reactive molecules of this product with one molecule of 1,2-Benzene diamine, as a new series of metal conversion complexes of Co(II), Ni(II), and Cu(II). The prepared ligand and their complexes characterized in the solid and solution states using spectroscopic techniques such as UV-Vis, FT.IR, 1 HNMR, and the elemental analyses as well as melting temperatures, molar conductivity, and magnetic susceptibility. The octahedral geometry around the central metal is suggested by molar conductivity, magnetic moment, molar ratio, and spectroscopic data about copper and cobalt ions, while tetrahedral around the nickel ion. After the incubation period at 37 °C for 24 h, the biological behavior of the binding produced with its anti-bacterial compounds against (Staphylococcus aureus and Escherichia coli) was examined at different concentrations (10, 50, and 200) ppm. The results showed that the performance of the prepared compounds was better in resisting and reducing the growth of bacteria tested at high concentrations.

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Exploration of semi-carbazone derivatives as promising agents against cholera: Insights from spectroscopic analysis, reactivity studies (ELF, HOMO-LUMO, NBO), solvation effects, and molecular docking investigations

Owen,

Anyambula,

Benson

et al. 2024

Chemical Physics Impact

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Synthesis, Spectroscopy and X-ray Crystallography Structure of Pyridine 4-Carbaldehyde Semicarbazone Schiff Base Ligand

Cited by 5 publications

References 27 publications

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Synthesis of Novel Tritopic Hydrazone Ligands: Spectroscopy, Biological Activity, DFT, and Molecular Docking Studies

Untitled

Exploration of semi-carbazone derivatives as promising agents against cholera: Insights from spectroscopic analysis, reactivity studies (ELF, HOMO-LUMO, NBO), solvation effects, and molecular docking investigations

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