Synthesis, DFT calculations and biological activity of a new Schiff base of 4-aminoantipyrine and its Co(II), Ni(II), Cu(II) and Zn(II) complexes and crystal structure of the Schiff base

Ramesh, A. R.; Pawar, Ravinder; Shyam, Perugu; Ramachandraiah, A.

doi:10.1007/s11164-021-04552-1

Cited by 10 publications

(4 citation statements)

References 42 publications

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“…has reported biological activity of Schiff bases of 4‐aminoantipyrine with copper(II), zinc(II), nickel(II), and cobalt(II) metals. The obtained results showed that Schiff bases of 4‐aminoantipyrine with Zn metals displayed the best antimicrobial activity compared with other metal complexes ligands [10] …”

Section: Introductionmentioning

confidence: 98%

“…The obtained results showed that Schiff bases of 4aminoantipyrine with Zn metals displayed the best antimicrobial activity compared with other metal complexes ligands. [10] In this context, the present investigation intends to study the binding interaction of an in house developed zinc(II) Schiff base with bovine serum albumin (BSA). The mentioned zinc(II) Schiff base is synthesized by Dasgupta et al [11] with functionalization at para position with methyl (Me), isopropyl ( i Pr), tertiary butyl ( t Bu) and chloride (Cl) compartmental ligands.…”

Section: Introductionmentioning

confidence: 99%

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Supramolecular Arrangement and DFT analysis of Zinc(II) Schiff Bases: An Insight towards the Influence of Compartmental Ligands on Binding Interaction with Protein

et al. 2022

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We report, for the first time, a detailed crystallographic study of the supramolecular arrangement for a set of zinc(II) Schiff base complexes containing the ligand 2,6-bis((E)-((2-(dimethylamino)ethyl)imino)methyl)-4-R-phenol], where R = methyl/tertbutyl/chloro. The supramolecular study acts as a pre-screening tool for selecting the compartmental ligand R of the Schiff base for effective binding with a targeted protein, bovine serum albumin (BSA). The most stable hexagonal arrangement of the complex [ZnÀ Me] (R = Me) stabilises the ligand with the highest FMO energy gap (ΔE = 4.22 eV) and lowest number of conformations during binding with BSA. In contrast, formation of unstable 3D columnar vertebra for [ZnÀ Cl] (R = Cl) tend to activate the system with lowest FMO gap (3.75 eV) with highest spontaneity factor in molecular docking. Molecular docking analyses reported in terms of 2D LigPlot + identified site A, a cleft of domains IB, IIIA and IIIB, as the most probable protein binding site of BSA. Arg144, Glu424, Ser428, Ile455 and Lys114 form the most probable interactions irrespective of the type of compartmental ligands R of the Schiff base whereas Arg185, Glu519, His145, Ile522 act as the differentiating residues with ΔG = À 7.3 kcal mol À 1 .

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Section: Introductionmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

Supramolecular Arrangement and DFT analysis of Zinc(II) Schiff Bases: An Insight towards the Influence of Compartmental Ligands on Binding Interaction with Protein

et al. 2022

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“…13 Schiff base ligands have drawn more attention due to the remarkable structural and synthetic characteristics, fine tunability, and chemical selectivity of the central metal atom. 14,15 The presence of the azomethine group (>C=N) in Schiff bases plays a pivotal role in controlling the behavior of central ions in a wide range of intriguing pharmaceutical and biological research. [16][17][18] A strategically designed Schiff base ligand framework can enhance the diagnostic and therapeutic nature of metal complexes by effectively modifying both the lipophilic-hydrophilic proportion of the resultant complex and the hard-soft nature of the coordinating metal ions.…”

Section: Introductionmentioning

confidence: 99%

“…Among the several ligands, metal complexes with nitrogen‐containing ligands have been investigated as potential drugs for medical and pharmacological uses 13 . Schiff base ligands have drawn more attention due to the remarkable structural and synthetic characteristics, fine tunability, and chemical selectivity of the central metal atom 14,15 . The presence of the azomethine group (>C=N) in Schiff bases plays a pivotal role in controlling the behavior of central ions in a wide range of intriguing pharmaceutical and biological research 16–18 .…”

Section: Introductionmentioning

confidence: 99%

Synthesis, spectroscopic elucidation, density functional theory calculation, and molecular docking studies of a novel series of tetradentate macrocyclic Schiff base ligands and their Zn(II) complexes and investigations of their antimicrobial, anti‐inflammatory, and anticancer activities

Mamta,

Pinki,

Chaudhary

2023

Applied Organom Chemis

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In the present work, novel Schiff base macrocyclic Zn(II) complexes [Zn(N8O4MacL1)Cl2–Zn(N8O4MacL3)Cl2] were synthesized by the reaction of ZnCl2 and macrocyclic ligands (N8O4MacL1–N8O4MacL3) derived from the condensation of ligand (L) and dicarboxylic acids [HOOC‐(CH2)n‐COOH]. The structural confirmation of the newly synthesized compounds was accomplished through various analytical techniques, including elemental analysis, infrared (IR) spectroscopy, nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), UV–visible spectroscopy, and powder X‐ray diffraction (XRD) studies. The spectral data provided evidence that the macrocyclic ligands acted as tetradentate ligands, forming coordination bonds with Zn(II) ions through the nitrogen atom of the imine (>C=N) group. The coordination complexes exhibited an octahedral geometry around the zinc ion, with two chloro groups covalently attached. Density functional theory (DFT) studies of the synthesized Schiff base macrocyclic compounds were carried out to determine their structural and electronic properties. The antimicrobial potential of the macrocyclic compounds was examined against a panel of pathogenic microbes, including four bacterial strains (Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Xanthomonas campestris) and two fungal strains (Fusarium oxysporum and Candida albicans). Then, the newly synthesized Schiff based macrocyclic compounds were evaluated for their anti‐inflammatory activity using an egg albumin method. The synthesized compounds were subjected to further evaluation to assess their potential as anticancer agents against MCF‐7 (human breast adenocarcinoma cell line), HCT‐116 (human colon cancer cell line), and A549 (human alveolar adenocarcinoma epithelial cell line). In addition, molecular docking studies were conducted to explore the potential interactions between the synthesized compounds and the target proteins VEGFR2 (PDB ID 1YWN), EGFR (PDB ID 1M17), and DNA gyrase B (PDB ID 4URO). It was found that there was a high correlation between the experimental results and the docking calculations.

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Microwave-assisted synthesis and notable applications of Schiff-base and metal complexes: a comparative study

Jain

Barman

2022

Res Chem Intermed

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Synthesis, DFT calculations and biological activity of a new Schiff base of 4-aminoantipyrine and its Co(II), Ni(II), Cu(II) and Zn(II) complexes and crystal structure of the Schiff base

Cited by 10 publications

References 42 publications

Supramolecular Arrangement and DFT analysis of Zinc(II) Schiff Bases: An Insight towards the Influence of Compartmental Ligands on Binding Interaction with Protein

Supramolecular Arrangement and DFT analysis of Zinc(II) Schiff Bases: An Insight towards the Influence of Compartmental Ligands on Binding Interaction with Protein

Synthesis, spectroscopic elucidation, density functional theory calculation, and molecular docking studies of a novel series of tetradentate macrocyclic Schiff base ligands and their Zn(II) complexes and investigations of their antimicrobial, anti‐inflammatory, and anticancer activities

Microwave-assisted synthesis and notable applications of Schiff-base and metal complexes: a comparative study

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