Synthesis, structural, spectral, computational, docking and biological activities of Schiff base (E)-4-bromo-2-hydroxybenzylidene) amino)-N-(pyrimidin-2-yl) benzenesulfonamide from 5-bromosalicylaldehyde and sulfadiazine

Kanagavalli, A.; Jayachitra, R.; Thilagavathi, G.; Padmavathy, M.; Elangovan, N.; Sowrirajan, S.; Thomas, Renjith

doi:10.1016/j.jics.2022.100823

Cited by 32 publications

(3 citation statements)

References 56 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Molecular docking analysis is often employed to predict the atomic interaction between the ligand molecule and a known target protein, which provides small molecule interaction behavior at target protein binding sites as well as elucidates key biochemical processes. , In recent years, H 2 L-based complexes have been found to have significant anticancer activity against various cancers . In this case, H 2 L, CuL, ZnL, and CoL molecules were docked with breast cancer-associated target protein HER2 [PDB: 3MZW].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Schiff Base Metal Complexes, Biological Activity, and Molecular Docking Studies

Venkatesh,

Vennila,

Kaya

et al. 2024

ACS Omega

View full text Add to dashboard Cite

New cobalt(II), copper(II), and zinc(II) Schiff metal complexes were synthesized by the condensation reaction of 4-nitrobenzene-1,2-diamine with 3−4-(diethylamino)-2-hydroxybenzaldehyde. Fourier transform infrared, nuclear magnetic resonance, ultraviolet−visible, electron paramagnetic resonance, and high-resolution electrospray ionization mass spectrometry and powder X-ray diffraction were used to characterize the synthesized H 2 L and its metal complexes. Conductance measurements, magnetic moment estimation, and metal estimation have all been determined and discussed. The electrochemical properties of the synthesized compounds have been determined and discussed using cyclic voltammetry. The molecular structures of H 2 L and its metal complexes have been optimized using the B3LYP functional and the 6-31G (d,p) basis set, and their parameters have been discussed. The quantum chemical properties of these synthesized compounds have been predicted through charge distribution and molecular orbital analysis. The biological properties of the synthesized compounds' antioxidant, antifungal, and antibacterial activity have been studied and discussed. Furthermore, H 2 L and its complexes have been docked with HER2associated target proteins in breast cancer.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Spectroscopic Characterization of Schiff Base Metal Complexes, Biological Activity, and Molecular Docking Studies

Venkatesh,

Vennila,

Kaya

et al. 2024

ACS Omega

View full text Add to dashboard Cite

show abstract

“…The contents of both beakers are subsequently transferred into an RB flask, which is then subjected to reflux for approximately 4 hours. The resulting chemical, which was collected, subjected to filtration, recrystallized utilizing DMSO as the solvent, dried, and subsequently characterized [13,14] . The synthesized scheme is presented in Figure 1.…”

Section: Methodsmentioning

confidence: 99%

“…The resulting chemical, which was collected, subjected to filtration, recrystallized utilizing DMSO as the solvent, dried, and subsequently characterized. [13,14] The synthesized scheme is presented in Figure 1.…”

Section: Synthesis Of (N-(pyrimidin-2-yl)-4-((177-trimethylbicyclo [2...mentioning

confidence: 99%

Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Elangovan,

Sowrirajan,

Arumugam

et al. 2024

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

A new class of (N‐(pyrimidin‐2‐yl)‐4‐((1,7,7‐trimethylbicyclo [2.2.1] heptan‐2‐ylidene) amino) benzenesulfonamide (CDA) was synthesized from commercially available camphor and sulfadiazine. The synthesized Schiff‐base was characterized by FT‐IR, 1H and 13C NMR spectroscopic analyses. The HOMO, LUMO, MEP, chemical reactivity parameters, and NBO were calculated using the WB97XD/cc‐pVDZ basis set. For better understanding, the electronic absorption and emission of the compound were recorded using UV‐Vis and fluorescence spectra. Molecular docking simulations were investigated between ligand (compound) and target protein. The computational results correlate well with observed values. The frontier molecular orbital energy gap (3.78 eV) revealed that the studied molecule has higher polarizability and chemical reactivity with lower kinetic stability. In addition, compound showed the highest binding score −5.72 kcal/mol, which was confirmed by a molecular docking simulation.

show abstract

Macrocyclic Schiff Base Complexes of Zn(II), Cu(II), Co(II), and Ni(II) Targeting Topoisomerase IIβ: Synthesis, Docking, and Evaluation as Potential Anticancer Agents

Yadav,

Singh

et al. 2024

Applied Organom Chemis

View full text Add to dashboard Cite

This study explores the potential of newly synthesized macrocyclic Schiff base metal complexes containing Zn(II), Cu(II), Ni(II) and Co(II) ions as Topoisomerase IIβ inhibitors. The complexes were derived from the condensation of 2,3‐diamino‐5‐bromopyridine and 2,5‐thiophenedicarboxaldehyde. Their formation was confirmed through various spectroscopic techniques. To gain insights into their structure and potential biological activity, computational modeling was employed. The density functional theory (DFT) was utilized to optimize the molecular geometries of the complexes. Furthermore, in silico docking simulations with the AutoDock Vina and GOLD scoring function investigated their binding interactions with Topoisomerase IIβ, an enzyme critical for cancer cell proliferation. The combined computational analysis revealed promising binding affinities for all complexes, with complex 3b demonstrating the most favorable interaction with the target enzyme having binding energy −8.56 kcal/mol. To validate these in silico predictions, the cytotoxicity of the complexes was evaluated using the established MTT assay. The observed cytotoxicity results complemented the anticipated binding patterns, with Cu(II) complex 3b demonstrating the strongest inhibitory effect on cancer cells with IC50 value 0.04 μM. Additionally, the hemolytic effect of the complexes on human red blood cells (hRBCs) was assessed to determine their biocompatibility. This strong correlation between predicted interactions, observed cytotoxicity, and minimal hemolytic effect highlights the potential of these complexes, particularly 3b, as promising leads for developing novel anticancer drugs targeting Topoisomerase IIβ. Future research will focus on elucidating the detailed mechanism of action of these complexes and exploring their broader pharmacological profile.

show abstract

Synthesis, structural, spectral, computational, docking and biological activities of Schiff base (E)-4-bromo-2-hydroxybenzylidene) amino)-N-(pyrimidin-2-yl) benzenesulfonamide from 5-bromosalicylaldehyde and sulfadiazine

Cited by 32 publications

References 56 publications

Synthesis and Spectroscopic Characterization of Schiff Base Metal Complexes, Biological Activity, and Molecular Docking Studies

Synthesis and Spectroscopic Characterization of Schiff Base Metal Complexes, Biological Activity, and Molecular Docking Studies

Synthesis, vibrational analysis, absorption and emission spectral studies, topology and molecular docking studies on sulfadiazine derivative

Macrocyclic Schiff Base Complexes of Zn(II), Cu(II), Co(II), and Ni(II) Targeting Topoisomerase IIβ: Synthesis, Docking, and Evaluation as Potential Anticancer Agents

Contact Info

Product

Resources

About