Structural, vibrational, fluorescence spectral features, Hirshfeld surface analysis, docking and drug likeness studies on 4-(2-bromo-4-methyl-phenoxymethyl)-6-methyl-coumarin derivative: Experimental and theoretical studies

In this work, we have reported the spectral and several other properties of 3‐(5‐bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxy‐phenyl)‐4H‐[1,2,4]triazole (BBT) molecule. Primarily, the experimental and computational analyses have been conducted for this molecule and compared the results. The computational studies have been conducted by Gaussian software with the help of DFT/B3LYP/6‐311++G (d, p) basis set. First, we have optimised BBT molecule to conduct the overall computational studies. The detailed computational and experimental vibrational analyses of BBT have been carried out. The electronic absorption and emission spectra of BBT have been observed in a variety of solvents with different solvent parameters like refractive index n, and dielectric constant ϵ. In solvatochromic studies, bathochromic (red) shift have observed in the absorption and emission spectra as an outcome of solute‐solvent interaction due to π → π* ${{\pi }^{{^\ast}}}$ transition. The solvent correlation methods experimentally investigated for the ground and excited‐state dipole moments. Along with these studies, we have also conducted Frontier Molecular Orbital (FMO) and Molecular Electrostatic Potential (MEP) analyses. Further, Molecular docking and drug likeness studies have also been performed to determine the pharmacological properties of the title molecule.

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“…The CÀ C stretching modes emerged around 1100-1650 cm À 1 . [56][57] In BBT, the DFT values found at 1049-…”

Section: Cà C Vibrationsmentioning

confidence: 99%

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Khemalapure¹,

Hiremath²,

Basanagouda³

et al. 2023

ChemistrySelect

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“…Solvatochromic methods were applied to calculate ground (μ g ) and excited (μ e ) state dipole moments. [24][25][26] DFT calculations were achieved in order to offer insight into the metal complexes and their activities. Furthermore, the docking study showed significant inhibition values to the VEGFR-2 enzyme, which promoted these complexes to be considerable VEGFR-2 inhibitors.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, TD‐DFT, molecular docking, biological applications, and solvatochromic studies of some new metal complexes derived from semicarbazone of pyrano[3,2‐c]quinoline‐3‐carboxaldehyde

Ibrahim

Emara

Taha

et al. 2023

Applied Organom Chemis

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New Zn(II), Cd(II), VO(IV), and UO2(VI) solvatochromic complexes derived from 6‐ethyl‐4‐hydroxy‐2,5‐dioxo‐5,6‐dihydro‐2H‐pyrano[3,2‐c]quinoline‐3‐carboxaldehyde‐semicarbazone ligand (H2L) were synthesized and established by elemental analyses, spectral (IR, UV, NMR, mass spectra), molar conductivity measurements, magnetic susceptibility, and thermal gravimetric analysis (TGA). The ligand coordinates with metal ions through ONO chelating sites, forming an octahedral geometry arrangement, except UO2(VI) that showed pentagonal bipyramidal geometry. Using Coats–Redfern methodology, the kinetic parameters (Ea, A, ΔH, ΔS, and ΔG) of the thermal decomposition steps were calculated and discussed. The complexes showed solvatochromic behavior that used to estimate the ground and excited state dipole moments. Optimization and structural parameters were carried out by density function theory (DFT) at B3LYP/GENECP method at 6‐311G(d,p) basis set for C, H, N, and O atoms and SDD (Stuttgart/Dresden) basis set for the metal atoms and interrelated with the experimental results. The complexes were tested for antimicrobial efficiency against Gram‐positive bacteria, Gram‐negative bacteria, yeast, and fungi. Also, antitumor activity was investigated against HepG‐2 cell line. Finally, the new synthesized complexes upon subjecting to molecular docking and distinguishable results showed outstanding inhibition results of VEGFR‐2 via achieving a high stabilization level inside the largest pocket of 1YWN protein.

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Novel Cu(II) and Zn(II) Nanocomplexes Based on 5,6‐Diphenyl‐1,2,4‐Triazine: Preparation, Spectroscopic, TD‐DFT Calculations, Molecular Docking and Solvatochromic Studies

Boshra,

Adly,

Abdelrhman

et al. 2024

Applied Organom Chemis

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The reaction between 2‐hydroxy‐1‐naphthaldehyde and 3‐hydrazino‐5,6‐diphenyl‐1,2,4‐triazine produced a novel hydrazone ligand (DTHMN), which reacted with Cu(II) and Zn(II) metal ion in molar ratio 1:1, giving octahedral Cu(II)‐DTHMN and tetrahedral Zn(II)‐DTHMN nanosized complexes. The structural geometries have been elucidated on the basis of elemental analysis, nuclear magnetic resonance, infrared, electronic, and electron spin resonance spectra, and magnetic and molar conductance measurements as well as x‐ray diffraction and thermal analysis. TEM analysis showed that Zn(II)‐DTHMN complex has nano‐rode morphology shape. On the other hand, Cu(II)‐DTHMN has sphere shape within nanodomain. The DTHMN ligand exhibits ONN chelating sites through N‐triazine ring, azomethine nitrogen, and deprotonated OH group, forming the mononuclear metal complexes. The synthesized compounds showed a distinct solvatochromic behavior in different polar solvents. A bathochromic alteration is observed when moving from less to high polar solvents, indicating strong solute–solvent interactions accompanied by intramolecular charge transfer (ICT). The ground and excited state dipole moments of these compounds were determined experimentally by solvatochromic shift method using Bilot–Kawski, Lippert–Mataga, Bakhshiev, and Kawski–Chamma–Viallet functions and a microscopic Reichardt's solvent polarity parameter (ETN). The dipole moment is increased significantly upon excitation referring to stabilizing the excited species includes n–π* transition by polarity of solvent. The experimental results are generally consistent with those values obtained by B3LYP/GENECP method at 6‐311G(d,p) basis set for C, H, N, and O atoms and SDD (Stuttgart/Dresden) basis set for the metal atoms. The compounds were tested for antimicrobial efficiency against Gram‐positive bacteria, Gram‐negative bacteria, and fungus strain. Finally, molecular docking was used to study the interactions between donors (the current compounds) and receptors FabH–CoA complex (PDB code: 1HNJ).

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Structural, vibrational, fluorescence spectral features, Hirshfeld surface analysis, docking and drug likeness studies on 4-(2-bromo-4-methyl-phenoxymethyl)-6-methyl-coumarin derivative: Experimental and theoretical studies

Cited by 11 publications

References 62 publications

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Design, Vibrational and Fluorescence Spectroscopic Properties, and Molecular Docking Studies of 3‐(5‐Bromobenzofuran‐3‐ylmethyl)‐5‐(4‐methoxyphenyl)‐4H‐[1,2,4]‐triazole by Experimental and Density Functional Theory Methods

Synthesis, characterization, TD‐DFT, molecular docking, biological applications, and solvatochromic studies of some new metal complexes derived from semicarbazone of pyrano[3,2‐c]quinoline‐3‐carboxaldehyde

Novel Cu(II) and Zn(II) Nanocomplexes Based on 5,6‐Diphenyl‐1,2,4‐Triazine: Preparation, Spectroscopic, TD‐DFT Calculations, Molecular Docking and Solvatochromic Studies

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