Copper complexes of pyrazolone-based Schiff base ligands: Synthesis, crystal structures and antibacterial properties

Poormohammadi, Elaheh B.; Behzad, Mahdi; Abbasi, Zeinab; Astaneh, Shakiba Darvish Alipour

doi:10.1016/j.molstruc.2019.127603

Cited by 23 publications

(7 citation statements)

References 34 publications

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“…The number and strength of hydrogen bonds formed between ligands and the lipase revealed L3 as the better binder compared to the other ligands, which is consistent with the experimental lipase inhibition result [34][35][36][37]. Comparing the biological activity of the three studied ligands with similar Schiff bases, the antibacterial and antioxidant activities were very close [31]. In general, Schiff bases have weak antibacterial activity compared to their transition metal ion complexes [26,30,[38][39][40][41].…”

Section: Antilipase Activity Of L1-l3 and Their Molecular Docking Investigationssupporting

confidence: 83%

“…It was found that L3 had no antibacterial activity against all tested Gram-negative bacteria and it was only active against Gram-positive S. aureus, resulting in an 11 mm inhibition zone. Several studies have shown that the in vitro biological evaluation of free compounds against various pathogenic bacterial strains are less powerful than their complexes with metals, such as copper, nickel, zinc, and cobalt [30,31].…”

Section: Antibacterial Screeningmentioning

confidence: 99%

“…In general, Schiff bases have weak antibacterial activity compared to their transition metal ion complexes [26,30,[38][39][40][41]. The difference is caused by the presence of active functional groups in the starting materials used to prepare the Schiff bases [30][31][32][33]35]. Therefore, if such compounds are required to have antibacterial activity, the functional groups of amines and carbonyls should be carefully selected.…”

Section: Antilipase Activity Of L1-l3 and Their Molecular Docking Investigationsmentioning

confidence: 99%

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Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-N-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Warad

Ali

et al. 2020

Molecules

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Three new tetradentate NNNS Schiff bases (L1–L3) derived from 2-(piperidin-4-yl)ethanamine were prepared in high yields. UV–Visible and FTIR spectroscopy were used to monitor the dehydration reaction between 2-(piperidin-4-yl)ethanamine and the corresponding aldehydes. Structures of the derived Schiff bases were deduced by 1H and 13C NMR, FTIR, UV–Vis, MS, EA, EDS, and TG-derived physical measurements. DFT/B3LYP theoretical calculations for optimization, TD-DFT, frequency, Molecular Electrostatic Potential (MEP), and highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) / were performed for L2. The in vitro antimicrobial activities of the three Schiff bases were evaluated against several types of bacteria by disk diffusion test using Gentamicin as the standard antibiotic. Schiff bases revealed good antioxidant activity by the DPPH method, and the IC50 values were compared to the Trolox standard. Pancreatic porcine lipase inhibition assay of the synthesized compounds revealed promising activity as compared to the Orlistat reference.

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Section: Antilipase Activity Of L1-l3 and Their Molecular Docking Investigationssupporting

confidence: 83%

Section: Antibacterial Screeningmentioning

confidence: 99%

Section: Antilipase Activity Of L1-l3 and Their Molecular Docking Investigationsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-N-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Warad

Ali

et al. 2020

Molecules

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“…Schiff bases and their metal complexes are widely used in medicinal and catalytic field due to their facial synthesis, higher stability, and chelating properties. [14][15][16] Among azoles, specifically, the 1,2,4-triazole core is an important chemical structure with a wide range of biological and therapeutic activities. The biological action of this motif is probably due to its high dipole character, strong hydrogen bonding capacity, high solubility, and rigidity.…”

Section: Introductionmentioning

confidence: 99%

Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Deswal

Asija

Tufail³

et al. 2023

Applied Organom Chemis

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In search of novel medications that could be effective in preventing and treating diabetes, four new [Co(L)(H 2 O) 3 ] (2), [Ni(L)(H 2 O) 3 ] (3), [Cu(L)(H 2 O)] (4) and [Zn(L)(H 2 O)] (5) complexes were synthesized from 4-Chloro-2-(((3-mercapto-5-[pyridin-4-yl]-4H-1,2,4-triazol-4-yl)imino)methyl)phenol ligand (H 2 L),which is obtained by the condensation of 5-chlorosalicylaldehyde with 4-amino-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol in 1:1 ratio. The Fouriertransform infrared spectroscopy (FTIR), nuclear magnetic resonance (NMR)( 1 H and 13 C), elemental analyses, UV-visible, electron spin resonance (ESR), thermogravimetric analysis (TGA), scanning electron microscopy, energy dispersive X-ray analysis (EDAX), and X-ray diffraction (XRD) studies were used to successfully characterize the compounds. The ligand act in a tridentate manner and coordinates to the metal ions through N azomethine , O phenolic and S thiol functionalities. On the premise of their spectral and physico-analytical data; octahedral geometry for complex 2 and 3, while square planar and tetrahedral geometry for complex 4 and 5 was proposed. Theoretical calculations of the synthesized compounds have been performed by using density functional theory (DFT)/B3LYP method and parameters such as HOMO-LUMO energy values and MESP were calculated. In vitro examinations against α-amylase and α-glucosidase reveal promising results for the compounds. Nickel (II) complex(3) against α-amylase and zinc (II) complex (5) against α-glucosidase were found to be good inhibitors. Molecular docking experiments against the receptors 1BSI and 5ZCC were done to support the observation and considerable

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“…Antipyrine is a derivative of pyrazolone, a wellknown compound used for analgesic and antipyretic drugs. The compound has several biologically active moieties in its structure, such as O, N, and methyl groups [1][2][3]. Aside from biological activities, antipyrine can form stable coordination bonds with central metal ions through carbonyl groups, such as the diketone complex containing transition metals, showing antibacterial activity [4].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Characterization and Antibacterial Properties of Nickel(II) Complex with 4-Aminoantipyrine Ligand

et al. 2021

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The novel nickel(II) complex has been successfully synthesized through the reaction of Ni(NO3)2·6H2O with 4-aminoantipyrine (AAP) ligand in a 1:3 mole ratio of Ni(II) to AAP. The complex was characterized using UV-Vis, Atomic Absorption Spectroscopy (AAS), Infrared spectrophotometry (IR), Thermogravimetry/Differential Scanning Calorimetry (TG/DSC), conductivity, and magnetic susceptibility. The complex formula was [Ni(AAP)3](NO3)2·5H2O. AAP was a bidentate ligand that coordinated through the primary amine nitrogen and the carbonyl oxygen to the nickel ion. The electronic spectra of the complex displayed two peaks at 646 nm and 385 nm in accordance with the 3A2g(F) → 3T1g(F) and 3A2g(F) → 3T1g(P) transitions, respectively. This complex gave a paramagnetic property with the effective magnetic moment (µeff) of 2.96 BM and the shape of an octahedron. The antibacterial test of this complex showed higher activity than the metal and its free ligand.

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Copper complexes of pyrazolone-based Schiff base ligands: Synthesis, crystal structures and antibacterial properties

Cited by 23 publications

References 34 publications

Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-N-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Synthesis and Spectral Identification of Three Schiff Bases with a 2-(Piperazin-1-yl)-N-(thiophen-2-yl methylene)ethanamine Moiety Acting as Novel Pancreatic Lipase Inhibitors: Thermal, DFT, Antioxidant, Antibacterial, and Molecular Docking Investigations

Instigating the in vitro antidiabetic activity of new tridentate Schiff base ligand appended M(II) complexes: From synthesis, structural characterization, quantum computational calculations to molecular docking, and molecular dynamics simulation studies

Synthesis, Characterization and Antibacterial Properties of Nickel(II) Complex with 4-Aminoantipyrine Ligand

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