Synthesis, spectroscopic characterization (FT-IR, FT-Raman, and NMR), quantum chemical studies and molecular docking of 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione

Avdović, Edina H.; Milenković, Dejan; Marković, Jasmina M. Dimitrić; Đorović, Jelena; Vuković, Nenad; Vukić, Milena; Jevtić, Verica V.; Trifunović, Srećko R.; Potočňák, Ivan; Marković, Zoran

doi:10.1016/j.saa.2018.01.023

Cited by 38 publications

(24 citation statements)

References 69 publications

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“…Fukui functions categorize and identify reactive sites and electron density at a given position within heterocyclic compounds upon donating or accepting electrons …”

Section: Resultsmentioning

confidence: 99%

“…Fukui function as an intramolecular reactivity index is calculated from NBO charges, which are represented by equation as given below:

\int f ((), r) italicdr = 1

…”

Section: Resultsmentioning

confidence: 99%

“…Coumarin compounds have high potential application and extensive significance in structural discovery . Density functional theory (DFT) provides valuable information on molecular reactivity and charge density‐based local reactivity descriptors, which play a significant role in the design of new pharmaceutical compounds . A literature survey on various heterocyclic compounds motivated us to undertake a study on quantum chemical computations and fluorescence spectral features of two coumarin compounds.…”

Section: Introductionmentioning

confidence: 99%

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Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

2020

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An attempt was made to determine the ground state and excited state dipole moments and quantum chemical computations of two coumarin compounds, namely 3‐hydroxy‐3‐[2‐oxo‐2‐(2‐oxo‐2H‐chromen‐3‐yl)‐ethyl]‐1,3‐dihydro‐indol‐2‐one (3HOCE) and 3‐[2‐(8‐methoxy‐2‐oxo‐2H‐chromen‐3‐yl)‐2‐oxo‐ethylidene]‐1,3‐dihydro‐indol‐2‐one (3MOCE). Both compounds displayed a red shift with enhancement in solvent polarity. The larger excited state dipole moment indicated the more polar nature of the selected compounds in the excited state than in the ground state. Kinetic stability and chemical reactivity of the selected compounds were studied with help of the quantum chemical properties of the compounds such as frontier molecular orbital analysis using density functional theory calculations with B3LYP/6–311+G (d, p) basis sets. Molecular electrostatic potential, Mulliken charges, natural bond orbital, and nonlinear optical properties were further studied. NBO analysis showed proton transfer within the selected donor–acceptor, depicting the large energy of stabilization for the compounds. The calculated Fukui function inferred the local softness and electrophilicity indices of used solute compounds.

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“…Fukui functions categorize and identify reactive sites and electron density at a given position within heterocyclic compounds upon donating or accepting electrons …”

Section: Resultsmentioning

confidence: 99%

“…Fukui function as an intramolecular reactivity index is calculated from NBO charges, which are represented by equation as given below:

\int f ((), r) italicdr = 1

…”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

2020

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“…[42][43][44] Thus, it allows envisaging centers and their relative reactivity towards electrophilic and nucleophilic attacks. 45 The molecular electrostatic potential surface was calculated at the B3LYP/6-31G(d) optimized geometry for structures 4a-4h. As showing in (Figure 3), electrophilic sites are red in color which designates the negative regions of the molecule, while the nucleophilic sites are colored in blue and designate the positive regions of the molecule.…”

Section: 2bmentioning

confidence: 99%

Novel series of acridone-1,2,3-triazole derivatives: microwave-assisted synthesis, DFT study and antibacterial activities

et al. 2019

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A series of novel acridones bearing a 1,2,3-triazole unit have been synthesized and characterized. The copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) was performed using both a conventional method and a microwave-assisted synthetic method. The in vitro antibacterial potencies of all the synthesized compounds were determined against five clinically isolated strains: Escherichia coli, Klebsiella pneumonia, Pseudomonas putida, Serratia marcescens and Staphyloccocus aureus. Furthermore, DFT quantum chemical calculations were carried out to investigate geometry structures, frontier molecular orbital and gap energies, and molecular electrostatic potential maps (MEP). Lipophilicities of the studied compounds were also determined.

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“…The protein Cytochrome P450 3A4 (CYP3A4) and methylenetetrahydrofolate reductase (MTHFR) were selected to conduct molecular docking studies on the basis of literature 47,48 and PASS online prediction (Table 1).…”

Section: Introductionmentioning

confidence: 99%

Click chemistry‐inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon‐based acid catalyst

Agarwal¹,

Sethiya

Teli

et al. 2020

Journal of Heterocyclic Chem

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A green and eco‐benign synthesis of biscoumarin derivatives using carbon sulfonic acid, a solid support catalyst has been described. The reaction involved a one‐pot two‐component reaction of 4‐hydroxycoumarin and aldehyde using carbon sulfonic acid involving Knoevenegal‐Michael condensation. A series of aromatic (bearing electron withdrawing and releasing group) and heteroaromatic aldehydes has been converted to biscoumarins with excellent isolated yields. The reaction is in compliance with green principles, that is, inexpensive catalyst, easy to prepare, nontoxic, easy handling, reusable up to five recycle runs, easy separation, short reaction time, no need of time consuming column purification, high yielding, and so on. The synthesized catalyst and biscoumarin derivatives were well characterized by spectral analysis. The molecular modeling studies showed that the designed molecular scaffolds (3a‐j) showed outstanding interaction with methylenetetrahydrofolate reductase (MTHFR) and cytochrome P450 3A4 (CYP3A4) proteins. It was noticed that 3f (−17.55 kJ/mol) and 3d (−26.23 kJ/mol) showed the highest docking score against CYP3A4 and MTHFR proteins, respectively.

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Synthesis, spectroscopic characterization (FT-IR, FT-Raman, and NMR), quantum chemical studies and molecular docking of 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione

Cited by 38 publications

References 69 publications

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Quantum chemical computations and photophysical spectral features studies of two coumarin compounds

Novel series of acridone-1,2,3-triazole derivatives: microwave-assisted synthesis, DFT study and antibacterial activities

Click chemistry‐inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon‐based acid catalyst

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