New Schiff base ligand and some of its coordination compounds: Synthesis, spectral, molecular modeling and biological studies

Abdel‐Rhman, Mohamed H.; El‐Asmy, Ahmed A.; Ibrahim, Reyad; Hosny, Nasser Mohammed

doi:10.1016/j.molstruc.2023.135023

Cited by 15 publications

(9 citation statements)

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“…FT-IR spectra Figure S1 illustrates the spectra of the unbound Schiff base ligand HL, which displayed distinct azomethine ν (C=N) bands at 1631 cm −1 . The spectra of the free Schiff base ligand also exhibited bands at 1278 cm −1 , which were assigned to the phenolic C-O stretching vibrations of HL [26]. Furthermore, aromatic ν(C−H) bending vibrations in the Schiff base ligand HL were observed within the approximate range of 875-636 cm −1 in previous studies [14,27,28].…”

Section: Resultsmentioning

confidence: 62%

Molecular docking studies, structural analysis, biological studies, and synthesis of certain novel Schiff base from benzohydrazide derivate

Gosu,

et al. 2024

Phys. Scr.

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The research described involves the synthesis and characterization of a new benzohydrazide based Schiff base compound namely 4-methyl-N'-(2,4,5-trimethoxybenzylidene) benzohydrazide (HL). The compound was synthesized by condensing a primary amine and an aldehyde functional group. The characterization of the compound was carried out using various spectroscopic techniques, including elemental analysis, Ultraviolet spectroscopy, nuclear magnetic resonance spectroscopy, and infrared spectroscopy. These techniques helped confirm the excellent quality of the synthesized molecules. In addition to the characterization, the Schiff base compound was subjected to docking studies and biological studies. The antibacterial activity of the compound was tested against three strains of bacteria, namely E. faecalis, B. subtills, and E.coli. The results of these tests provided information on the compound effectiveness against these bacterial strains. Furthermore, docking studies was performed to assess the interaction between the synthesized compound and three target enzymes like GlcN-6-p synthase, DNA polymerase, and EGFR tyrosine kinase. Docking studies are computational simulations that provide insights into the binding interactions between Schiff base ligand and target proteins. In this case, the docking studies helped understand the potential mechanisms of action of the synthesized compound by calculating binding constants and the number of binding modes. The biological activity studies revealed interesting fragmentation patterns, which could be further investigated to understand the compound modes of action. Moreover, the docking studies evaluated the compound's potential as a drug candidate by assessing its binding interactions with the target enzymes. The present study suggests that the synthesized benzohydrazide based Schiff base compound exhibits potential antibacterial activity and shows promising binding interactions with the target protein/enzymes. This information is valuable for designing and developing more potent compounds in the future.

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Section: Resultsmentioning

confidence: 62%

Molecular docking studies, structural analysis, biological studies, and synthesis of certain novel Schiff base from benzohydrazide derivate

Gosu,

et al. 2024

Phys. Scr.

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“…The ligand (H 2 L) has two possible tautomeric forms, keto and enol, as shown in Structure 1 , therefore, its IR spectrum was carefully studied in order to determine in which form the ligand is existed. The spectrum displayed sharp band at 3248 cm −1 with a shoulder at 3142 cm −1 ascribed to the hydroxyl group ν(OH) [ 33 , 42 , 43 ] and hydrazonyl ν(NH) [ 33 , 43 ], respectively. In addition, the strong band at 1635 cm −1 with shoulder at 1610 cm −1 were designated to the carbonyl ν(C=O) [ 33 , 43 ] and azomethine ν(C=N) [ 33 , 43 ], respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The spectrum displayed sharp band at 3248 cm −1 with a shoulder at 3142 cm −1 ascribed to the hydroxyl group ν(OH) [ 33 , 42 , 43 ] and hydrazonyl ν(NH) [ 33 , 43 ], respectively. In addition, the strong band at 1635 cm −1 with shoulder at 1610 cm −1 were designated to the carbonyl ν(C=O) [ 33 , 43 ] and azomethine ν(C=N) [ 33 , 43 ], respectively. Furthermore, the aromatic ν(C=C) along with the furane ν as (C–O–C) and ν s (C–O–C) vibrations [ 44 , 45 ] were observed at 1588, 1237 and 1017 cm −1 , respectively (Fig.…”

Section: Resultsmentioning

confidence: 99%

“…Furan-2-carbaldehyde (1.2 mL, 0.01 mol) was added drop wisely to ethanolic solution of 2-hydroxybenzohydrazide (1.52 g, 0.01 mol) then a few drops of glacial acetic acid were added. The reaction mixture was heated under reflux for 4 h where a faint brown precipitate of N′ -(furan-2-ylmethylene)-2-hydroxybenzohydrazide was formed [ 33 ]. While hot, the precipitate was filtered off, washed successfully with ethanol, dried and recrystallized from hot ethanol (m.p.…”

Section: Methodsmentioning

confidence: 99%

“…To ethanolic solution of H 2 L (0.02 mol), a water solution of the Cu(II), Co(II), Ni(II) or Zn(II) acetate (0.01 mmol) were added dropwise with stirring. The reaction mixture was refluxed for 2 h [ 22 , 33 ]. The precipitates were filtered off, washed with hot ethanol followed by diethyl ether and dried in a vacuum desiccator over anhydrous CaCl 2 .…”

Section: Methodsmentioning

confidence: 99%

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N′-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling

Hosny,

Samir,

Abdel-Rhman

2024

BMC Chemistry

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The ligand, N′-(furan-2-ylmethylene)-2-hydroxybenzohydrazide (H2L), was synthesized characterized through various spectral studies which cleared out that the free ligand existed in keto form. The ligand upon reaction with Cu(II), Co(II), Ni(II) and Zn(II) acetates yielded complexes with stoichiometric ratio 1:2 (M:L) which has been validated through the elemental and mass spectral measurements. The IR and NMR spectral studies of the isolated complexes disclosed that the ligand chelated to metal ion in mononegative bidentate fashion via the azomethine nitrogen and deprotonated enolized carbonyl oxygen. Moreover, the DFT quantum chemical calculations designated that the ligand and Ni(II) complex exhibited the highest and lowest values of HOMO, LUMO energies and HOMO-LUMO energy gap, respectively. Furthermore, the in vitro cytotoxic activity towards HePG-2 and HCT-116 cell lines of the isolated compounds was investigated and the data cleared out that the ligand was more potent than the metal complexes.

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Spectroscopic, Structural Analysis, Molecular Orbital, Molecular Docking, and Antibacterial Activity of the Thiocarbohydrazone Ligand and Its Complexes

Gomha,

Saleh,

El‐Sayed

et al. 2025

Applied Organom Chemis

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New thiocarbohydrazone ligand (N′‐((E)‐3,3‐diphenyl‐2,3‐dihydro‐1H‐inden‐1‐ylidene)‐2‐((Z)‐2‐oxoindolin‐3‐ylidene)hydrazine‐1‐carbothiohydrazide; H2L) and its Co (II), Ni (II), Fe (III), Cu (II), Cd (II), Zn (II), and Mn (II) complexes were prepared in good yields ranging from 60% to 90% and characterized by spectroscopic and analytical tools. Uv–vis, magnetic measurements, molar conductivity, 1H‐NMR spectra, elemental analyses, and FT‐IR were performed. The structural formula for the examined ligand was improved using the Gaussian09 tool. The morphology of the thiocarbohydrazone ligand and metal complexes was demonstrated using a scanning electron microscope. The prepared thiocarbohydrazone ligand and its complexes were evaluated for their antimicrobial properties against Streptococcus mutans and Staphylococcus aureus as G‐positive bacteria; Escherichia coli, Klebsiella pneumoniae, and Pseudomonas aeruginosa as G‐negative bacteria; and some species of fungi as Aspergillus niger and Candida albicans. It was found that thiocarbohydrazone ligand was less biologically active than the targeted complexes as indicated from the obtained inhibition zone diameters. The interaction between the ligand and the amino acids of the proteins of G‐positive bacteria (Staphylococcus typhus‐3ty7), G‐negative bacteria (E. coli‐3t88), and fungi (C. albicans‐5k04) as receptors was investigated using molecular docking study to correlate the experimental and theoretical observations.

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New Schiff base ligand and some of its coordination compounds: Synthesis, spectral, molecular modeling and biological studies

Cited by 15 publications

References 50 publications

Molecular docking studies, structural analysis, biological studies, and synthesis of certain novel Schiff base from benzohydrazide derivate

Molecular docking studies, structural analysis, biological studies, and synthesis of certain novel Schiff base from benzohydrazide derivate

N′-(Furan-2-ylmethylene)-2-hydroxybenzohydrazide and its metal complexes: synthesis, spectroscopic investigations, DFT calculations and cytotoxicity profiling

Spectroscopic, Structural Analysis, Molecular Orbital, Molecular Docking, and Antibacterial Activity of the Thiocarbohydrazone Ligand and Its Complexes

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