Vibrational and Hirshfeld surface analyses, quantum chemical calculations, and molecular docking studies of coumarin derivative 3-(1-m-toluidinoethylidene)-chromane-2,4-dione and its corresponding palladium(II) complex

Milenković, Dejan; Avdović, Edina H.; Dimić, Dušan; Sudha, S.; Ramarajan, D.; Milanović, Žiko; Trifunović, Srećko R.; Marković, Zoran

doi:10.1016/j.molstruc.2020.127935

Cited by 52 publications

(16 citation statements)

References 57 publications

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“…All calculations were performed by employing the Gaussian09 program package and B3LYP-D3BJ functional in conjunction with 6-311++G(d,p) basis set (with polarization and diffuse functions included) [26,27]. In previous studies, it has been shown that the B3LYP-D3BJ method reproduces experimental geometrical parameters well [28,29]. The vibrational spectra were analyzed by the Potential Energy Distribution (PED) analysis [30] and FCART version 7.0 software [31].…”

Section: Computational Methodologymentioning

confidence: 99%

Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives

Milanović¹,

Marković²,

Dimić³

et al. 2021

Comptes Rendus. Chimie

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In the present manuscript, three different 4,7-dihydroxycoumarin derivatives were prepared and structurally characterized by crystallographic and spectroscopic techniques in combination with the B3LYP-D3BJ theoretical method. Cytotoxic and antimicrobial activities of investigated compounds were screened against different cell lines and microorganisms. HCT-116 cells were most sensitive to the 3-(1-(2-hydroxyphenyl)amino) ethylidene)-2,4-dioxochroman-7-yl acetate derivative, while the best antimicrobial activity against Bacillus subtilis ATCC 6633 was shown by 3-(1-(2hydroxyphenyl)amino)ethylidene)-2,4-dioxochroman-7-yl acetate. The molecular docking study for * Corresponding author.

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Section: Computational Methodologymentioning

confidence: 99%

Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives

Milanović¹,

Marković²,

Dimić³

et al. 2021

Comptes Rendus. Chimie

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“…The red area represents the O–H interaction, and the deeper the red color, the stronger the O−H interaction. [ 59 ] The distribution of the interactions of C−H, Br−H, and H−H is mainly in the lighter color region. The distribution of hydrogen bond interactions can be roughly inferred from the diagram, which is helpful to further explore the internal factors of the stability of the complexes.…”

Section: Resultsmentioning

confidence: 99%

Investigation of mononuclear, dinuclear, and trinuclear transition metal (II) complexes derived from an asymmetric Salamo‐based ligand possessing three different coordination modes

Bian

Wang

et al. 2020

Applied Organom Chemis

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A new asymmetric Salamo-based ligand H 2 L was synthesized using 3-tert-butyl-salicylaldehyde and 6-methoxy-2-[O-(1-ethyloxyamide)]-oxime-1-phenol. By adjusting the ratio of the ligand H 2 L and Cu (II), Co (II), and Ni (II) ions, mononuclear, dinuclear, and trinuclear transition metal (II) complexes, [Cu(L)], [{Co(L)} 2 ], and [{Ni(L)(CH 3 COO)(CH 3 CH 2 OH)} 2 Ni] with the ligand H 2 L possessing completely different coordination modes were obtained, respectively. The optical spectra of ligand H 2 L and its Cu (II), Co (II) and Ni (II) complexes were investigated. The Cu (II) complex is a mononuclear structure, and the Cu (II) atom is tetracoordinated to form a planar quadrilateral structure. The Co (II) complex is dinuclear, and the two Co (II) atoms are pentacoordinated and have coordination geometries of distorted triangular bipyramid. The Ni (II) complex is a trinuclear structure, and the terminal and central Ni (II) atoms are all hexacoordinated, forming distorted octahedral geometries. Furthermore, optical properties including UV-Vis, IR, and fluorescence of the Cu (II), Co (II), and Ni (II) complexes were investigated. Finally, the antibacterial activities of the Cu (II), Co (II), and Ni (II) complexes were explored. According to the experimental results, the inhibitory effect was found to be enhanced with increasing concentrations of the Cu (II), Co (II), and Ni (II) complexes.

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“…A density functional theory (DFT) study was positively led by means of Gaussian 09 using B3LYP as a functional method along the 6-31G(d,p) basis set to minimize the energy of compounds. − The B3LYP method mainly comprises Becke’s three-parameter (B3) exchange functional in conjunction with the Lee Yang and Parr (LYP) associated functional . Gauss View 5.0 software was run to calculate the energy gap measurement of the synthesized compounds and other outcomes of the DFT studies .…”

Section: Methodsmentioning

confidence: 99%

Therapeutical Potential of Imines; Synthesis, Single Crystal Structure, Computational, Molecular Modeling, and ADMET Evaluation

et al. 2022

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Imines are multipurpose pharmacophores, simply accessible compounds, and have a broad range of usage in several areas of chemistry especially in medicine. Two novel compound imines, ( E )-4-methyl-2-(( o -tolylimino)methyl)phenol ( 1 ) and ( E )-2-(((4-methoxybenzyl)imino)methyl)-4-methylphenol ( 2 ), were synthesized with effective product via reported protocol in the literature. Single crystal X-ray diffraction (SCXRD) was employed for structural exposition, disclosing that both compounds are orthorhombic. To optimize the newly designed imines, a B3LYP functional with a basis set 6-31G(d,p) was mainly considered. DFT results were utilized to check correlation between the data recovered from SCXRD outcomes and also to measure the energy difference. Hirshfeld surface study was done to demonstrate the intermolecular contacts along the percentage of interaction in the overall crystalline compound. Molecular operating environment program was tested against AChE and BChE enzymes to perform a modeling study of the compounds. The docking score and binding affinity of the compounds revealed that 2 showed comparatively more inhibition than 1 . In silico ADMET studies exposed the physiochemical nature of these novel compounds, and it also unveiled that both compounds behaved as drug-like candidates.

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Vibrational and Hirshfeld surface analyses, quantum chemical calculations, and molecular docking studies of coumarin derivative 3-(1-m-toluidinoethylidene)-chromane-2,4-dione and its corresponding palladium(II) complex

Cited by 52 publications

References 57 publications

Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives

Synthesis, structural characterization, biological activity and molecular docking study of 4,7-dihydroxycoumarin modified by aminophenol derivatives

Investigation of mononuclear, dinuclear, and trinuclear transition metal (II) complexes derived from an asymmetric Salamo‐based ligand possessing three different coordination modes

Therapeutical Potential of Imines; Synthesis, Single Crystal Structure, Computational, Molecular Modeling, and ADMET Evaluation

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