Synthesis, Characterization and in vitro Biological Evaluation of a New Schiff Base Derived from Drug and its Complexes with Transition Metal Ions

Mumtaz, Amina; Mahmud, Tariq; Elsegood, Mark R. J.; Weaver, George W.

doi:10.37358/rc.18.7.6393

Cited by 5 publications

(9 citation statements)

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“…The integrated ligand and transition metal complexes were screened against various bacteria and fungus. The studies demonstrated the enhanced activity of metal complexes against reported microbes compared to free ligand [11].…”

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confidence: 94%

Synthesis, Characterization and Biological Evaluation of Schiff Base (N-4-(thiophene-2-yl-methyleneamino)-2,6-dimethylpyrimidine-4-yl)benzenesulfonamide and its Complexes with Cu(II), Ni(II), Co(II), Fe(II), Mn(II), Zn(II) Ions

Mumtaz¹,

Mahmud²,

Elsegood³

et al. 2020

Rev. Chim.

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Two step synthesis of Schiff base ligand and its transition metal complexes was done by condensation reaction. In first step, the drug and aldehyde in equimolar ratio were refluxed for one hour at pH 8-9 in order to get Schiff base ligand. In second step, ligand and metal salts were refluxed for 2 hour. The ligand and Cu(II), Ni(II), Co(II), Fe(II), Mn(II), Zn(II) complexes were characterized by using different instruments like FT-IR, 1H-NMR, 13C-NMR, Mass, Atomic absorption spectrometer, Elemental analyzer, UV-visible spectrophotometer, Evans balance, Conductivitymeter and Thermogravimeter. In vitro antibacterial, antifungal and anti-inflammatory activities were also studied. The synthesized ligand and transition metal complexes were tested against Escherichia coli, Enterobacter aerogenes, Staphylococcus aureus, Bacillus pumilus, Klebsiella oxytoca, Clostridium butyrium, Mucor and Aspergillus niger. These studies demonstrated the enhanced activity of metal complexes against reported bacterial and fungal strains when compared with free Schiff base ligand. The Cu(II) complex recognized as anti-inflammatory agent while the parent drug showed no activity.

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mentioning

confidence: 94%

Synthesis, Characterization and Biological Evaluation of Schiff Base (N-4-(thiophene-2-yl-methyleneamino)-2,6-dimethylpyrimidine-4-yl)benzenesulfonamide and its Complexes with Cu(II), Ni(II), Co(II), Fe(II), Mn(II), Zn(II) Ions

Mumtaz¹,

Mahmud²,

Elsegood³

et al. 2020

Rev. Chim.

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Section: Introductionmentioning

confidence: 99%

“…Schiff bases have been regarded as important ligands due to their contribution to coordination chemistry due to their variable bonding, structural possibilities, and their applications in several fields; they can be simply prepared and associated with many metal ions without any requirement of purification because water is the only byproduct of condensation. [1][2][3] They have an amine group, similar to the natural biological systems, so they have different applications and functions as observing the conversion mechanism, racemization reaction in biological systems, biological probes, acting as antitumor, anti-HIV, antibacterial, antifertility, antimosquito larval, anti-inflammatory, and anticancer, DNA cleaving agents. [4][5][6] Beside biological activities, Schiff bases are also used as dyes, pigments, catalysts, and corrosion inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Antibacterial and anticorrosion behavior of bioactive complexes of selected transition metal ions with new 2‐acetylpyridine Schiff base

Deghadi

Elsharkawy

Ashmawy

et al. 2022

Applied Organom Chemis

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Successful preparation of Schiff base 4‐(4‐aminophenoxy)‐N‐(1‐(pyridin‐2‐yl)ethylidene)aniline derived from refluxing of 4,4‐oxydianniline with 2‐acetylpyridine within 2 h in 1:1 molar ratio was performed. Different transition metal complexes were synthesized by reacting metal chlorides with the formed ligand in 1:1 molar ratio. Structural features of the complexes were obtained from different tools such as infrared (IR), 1H‐nuclear magnetic resonance (1H‐NMR), ultraviolet–visible (UV‐vis), molar conductivity, thermogravimetric (TG)/differential thermogravimetric (DTG), microanalysis, and mass spectrometry. All complexes had an octahedral structure and Schiff base acted as a neutral bidentate ligand that linked to metal centers via N‐azomethine and N‐pyridine atoms. Cr(III), Fe(III), and Ni(II) complexes were electrolytes while other complexes were nonelectrolytes. The molecular structure of Schiff base was optimized theoretically and its HOMO and LUMO energies were dictated by B3LYP/DFT calculations. The in vitro antibacterial activity versus some selected bacteria species showed that all prepared compounds were biologically active except Fe(III) complex against certain species and Co(II) complex had the highest biological activity values. Molecular docking was used to determine effective binding modes between ligand and its [Co(L)(H2O)2Cl2]·4H2O complex with active sites of 4WJ3, 4ME7, 4K3V, and 3T88 receptors. The strongest binding of Co(II) complex was with the 4ME7 receptor with lowest binding energy value −25.4 kcal mol−1. Schiff base as corrosion inhibitors for mild steel in 1.0‐M HCl had been investigated using electrochemical impedance spectroscopy (EIS), potentiodynamic polarization (PP), and electrochemical frequency modulation (EFM). The results showed that the inhibitor acts as a mixed‐type inhibitor. The inhibition efficiency increases with increasing inhibitor concentration to its maximum of 97.5% at 1 × 10−3 M solution. The adsorption model obeys the Langmuir isotherm, and Gibbs free energy was around −40 kJ/mol, indicating that it is spontaneously and chemically adsorbed on the surface. SEM/EDX results proved the sticking of a barrier film on the mild steel sample.

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“…Schiff bases were discovered first time by the chemist Hugo Schiff in 1864 [1]. These are condensation products of carbonyl compounds and amines [2], also called as imine or azomethine due to (-HC=N-) functional group [3], here nitrogen atom serves as bonding molecule for complexation.In azomethine derivatives, the C‚N linkage is essential for biological activity [4,5], several azomethine have been reported to possess remarkable antibacterial, antifungal, anticancer and antimalarial activities [6][7][8][9].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and Biological Evaluation of New Schiff Base Ligand derived from 3-hydroxy-benzaldehyde and p-toluidine and its Divalent Metal Ions

Mazhar¹,

Aftab²,

Mahmud³

et al. 2020

Rev. Chim.

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A new Schiff base ligand (L) and its transition divalent metal complexes were prepared by the condensation reaction; Reaction was carried out at 70-80 oC by refluxing equimolar ratio of toluidine and aldehyde by continuous stirring for 5-6 hours. Synthesized ligand and Ni(II), Fe(II), Co(II), Mn(II) and Zn(II) bimetallic complexes were characterized by using FT-IR, UV-visible spectroscopy, AAS, Single crystal X-ray analysis, 1H-NMR, molar conductance. Compounds were screened against two fungus Candida glabrata and Candida albicans by agar tube dilution protocol. In vivo anti-inflammatory activity via induced paw edema method and in vitro results by heat induced protein denaturation method were checked. Synthesized compounds were also showed antioxidant activity by using DPPH (diphenylpicrylhydrazyl) and Trolox was used as standard. These studies show that ligand and almost all metal complexes are reactive towards biological assays against reported standard drugs. Zn-L indicates more activeness for antioxidant activity and free ligand while Co-L recognized as more effective anti-inflammatory drug.

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Synthesis, Characterization and in vitro Biological Evaluation of a New Schiff Base Derived from Drug and its Complexes with Transition Metal Ions

Cited by 5 publications

References 0 publications

Synthesis, Characterization and Biological Evaluation of Schiff Base (N-4-(thiophene-2-yl-methyleneamino)-2,6-dimethylpyrimidine-4-yl)benzenesulfonamide and its Complexes with Cu(II), Ni(II), Co(II), Fe(II), Mn(II), Zn(II) Ions

Synthesis, Characterization and Biological Evaluation of Schiff Base (N-4-(thiophene-2-yl-methyleneamino)-2,6-dimethylpyrimidine-4-yl)benzenesulfonamide and its Complexes with Cu(II), Ni(II), Co(II), Fe(II), Mn(II), Zn(II) Ions

Antibacterial and anticorrosion behavior of bioactive complexes of selected transition metal ions with new 2‐acetylpyridine Schiff base

Synthesis, Characterization and Biological Evaluation of New Schiff Base Ligand derived from 3-hydroxy-benzaldehyde and p-toluidine and its Divalent Metal Ions

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