Synthesis and comprehensive spectroscopic (X-ray, NMR, FTIR, UV–Vis), quantum chemical and molecular docking investigation of 3-acetyl-4‑hydroxy‑2-oxo-2H-chromen-7-yl acetate

Milanović, Žiko; Dimić, Dušan; Avdović, Edina H.; Milenković, Dejan; Marković, Jasmina Dimitrić; Klisurić, Olivera R.; Trifunović, Srećko R.; Marković, Zoran

doi:10.1016/j.molstruc.2020.129256

Cited by 37 publications

(20 citation statements)

References 61 publications

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“…The synthesis of the 4,7-dihydroxycoumarin derivatives (3a-3c) was performed according to Scheme 1. New coumarin derivatives were synthesized in the reaction of the previously synthesized compound (1) [12] and different aminophenol derivatives (2) (0.002 mol) at 3-hour reflux in ethanol (50 ml). Progress of reactions was monitored by Thin Layer chromatography (toluene:acetone = 7:3).…”

Section: General Synthesis Proceduresmentioning

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: General Synthesis Proceduresmentioning

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 other aromatic stretching vibrations are at lower frequencies with PED contributions of 10–50%, indicating mixed modes (symmetric and asymmetric modes) of vibrations. 48,49…”

Section: Resultsmentioning

confidence: 99%

Design, synthesis, structural analysis and quantum chemical insight into the molecular structure of coumarin derivatives

Sundaramurthy

Nataraju

Lokanath

2022

Mol. Syst. Des. Eng.

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“…The conformational search was performed to verify that the global minima were obtained. These results were partially based on the rotation of the C7-O4 bond for a structurally similar molecule as given in [33] and the fact that intramolecular hydrogen bond is formed when the OH group points towards -OCH3 group. The solvent effect was approximated by the Conductor-like Polarizable Continuum Model (CPCM) using methanol (ε = 32.61) and water (ε = 78.36) as solvents to mimic experimental environments [41].…”

Section: Computational Methodologymentioning

confidence: 97%

“…Compound 3-acetyl-4-hydroxy-2-oxo-2H-chromen-7-yl acetate (1) was prepared as described in reference [33]. New coumarin derivatives (A-3OH and A-4OH) were synthesized in the reaction of the previously synthesized compound 1 and aniline derivatives (2) (0.002 mol): 4-amino-2-methoxyphenol and 5-amino-2-methoxyphenol, at 3h reflux in ethanol (50 mL) (Scheme 1).…”

Section: General Synthesis Proceduresmentioning

confidence: 99%

Mechanism of Antiradical Activity of Newly Synthesized 4,7-Dihydroxycoumarin Derivatives-Experimental and Kinetic DFT Study

Milanović

Dimić

Žižić

et al. 2021

IJMS

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Coumarin derivatives have proven beneficial biological activities, but the mechanism of their radical scavenging potency is not fully understood. In this study, the antiradical capacity of two newly synthesized 4,7-dihydroxycoumarin derivatives: (E)-3-(1-((3-hydroxy-4-methoxyphenyl)amino)-ethylidene)-2,4-dioxochroman-7-yl acetate (A-3OH) and (E)-3-(1-((4-hydroxy-3-methoxyphenyl)amino)ethylidene)-2,4-dioxochroman-7-yl acetate (A-4OH) towards HO• were examined by Electron Paramagnetic Resonance (EPR) Spectroscopy and Density Functional Theory (DFT). The compounds were fully characterized by the elemental microanalysis, IR, and NMR spectroscopies. The effect of pH on the acid–base equilibria is separately discussed and the predominant species at the physiological pH were determined. Several common mechanisms (Hydrogen Atom Transfer (HAT), Single-Electron Transfer followed by Proton Transfer (SET-PT), Sequential Proton Loss followed by Electron Transfer (SPLET), Radical Adduct Formation (RAF), and Intramolecular Hydrogen Atom Abstraction (iHAA)) of radical scavenging were investigated based on thermodynamic and kinetic parameters. EPR results indicated that both compounds significantly reduce the amount of present HO•. The results of the kinetic DFT study demonstrated that both compounds predominantly exhibit antiradical capacity through HAT and SPLET mechanisms. The estimated overall rate constants (koverall) proved that A-4OH shows better antioxidant capacity than A-3OH which is well-correlated with the results obtained by EPR measurement.

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Synthesis and comprehensive spectroscopic (X-ray, NMR, FTIR, UV–Vis), quantum chemical and molecular docking investigation of 3-acetyl-4‑hydroxy‑2-oxo-2H-chromen-7-yl acetate

Cited by 37 publications

References 61 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

Design, synthesis, structural analysis and quantum chemical insight into the molecular structure of coumarin derivatives

Mechanism of Antiradical Activity of Newly Synthesized 4,7-Dihydroxycoumarin Derivatives-Experimental and Kinetic DFT Study

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