Synthesis, quantum chemical study, AIM simulation, in silico ADMET profile analysis, molecular docking and antioxidant activity assessment of aminofuran derivatives

Azad, Iqbal; Akhter, Yusuf; Khan, Tahmeena; Azad, Mohammad Irfan; Chandra, Subhash; Singh, Praveer; Kumar, Durgesh; Nasibullah, Malik

doi:10.1016/j.molstruc.2019.127285

Cited by 38 publications

(16 citation statements)

References 52 publications

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“…Therefore, the principal objective of this work was to investigate the structure, electronic and optical properties of these same derivatives (Figure 1), in order to establish the relationship between the chemical substitutions and computed molecular properties to aid in the design of materials with potential optoelectronic applications [26]. To do so, we employed density functional theory (DFT) [27], by far the most popular quantum mechanical method to calculate the structure and electronic properties of the molecules [28][29][30]. A detailed computational investigation was performed on the four coumarin-derivatives, which were selected on the basis of their enzyme inhibition capability [13].…”

Section: Introductionmentioning

confidence: 99%

“…Several computational DFT studies have investigated molecular properties of coumarin derivatives for applications such as optoelectronics [26,32], solar cells [7,[33][34][35][36], fluorescent dyes and lasers [7,37]. To do so, we employed density functional theory (DFT) [27], by far the most popular quantum mechanical method to calculate the structure and electronic properties of the molecules [28][29][30]. A detailed computational investigation was performed on the four coumarin-derivatives, which were selected on the basis of their enzyme inhibition capability [13].…”

Section: Introductionmentioning

confidence: 99%

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Substitution Effects on the Optoelectronic Properties of Coumarin Derivatives

et al. 2019

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Coumarin derivatives have gathered major attention largely due to their versatile utility in a wide range of applications. In this framework, we report a comparative computational investigation on the optoelectronic properties of 3-phenylcoumarin and 3-heteroarylcoumarin derivatives established as enzyme inhibitors. Specifically, we concentrate on the variation in the optoelectronic characteristics for the hydroxyl group substitutions within the coumarin moiety. In order to realize our aims, all-electron density functional theory and time dependent density functional theory calculations were performed with a localized Gaussian basis-set matched with a hybrid exchange–correlation functionals. Molecular properties such as highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) energies, vertical ionization (IEV) and electron affinity energies, absorption spectra, quasi-particle gap, and exciton binding energy values are examined. Furthermore, the influence of solvent on the optical properties of the molecules is considered. We found a good agreement between the experimental (8.72 eV) and calculated (8.71 eV) IEV energy values for coumarin. The computed exciton binding energy of the investigated molecules indicated their potential optoelectronics application.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Substitution Effects on the Optoelectronic Properties of Coumarin Derivatives

et al. 2019

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“…Using HOMO and LUMO values the quantum chemical parameters such as ionization potential (I), electron affinity (A), electronegativity (χ), chemical hardness (η), Global softness (S), chemical potential (μ), electrophilicity index (ω), net electrophilicity (

), electron accepting (ω + ) and donating capability (ω − ), Chemical softness (σ), nucleophilicity index (N), additional electronic charges (ΔN max ) and optical softness (σ 0 ) [ 45 - 47 ] have been calculated with the help of Eqs. (1) , (2) , (3) , (4) , (5) , (6) , (7) , (8) , (9) , (10) , (11) , (12) , (13) , (14) , and (15) and given in Table 5 .…”

Section: Resultsmentioning

confidence: 99%

“…Nucleophilicity index and electrophilicity index are also related to the biological activity of a molecule. The reactivity of the molecule increasing with increased nucleophilicity index [ 45 ].…”

Section: Resultsmentioning

confidence: 99%

Design, docking, and DFT investigations of 2,6-bis(3,4-dihydroxyphenyl)-3-phenethylpiperidin-4-one

Sasitha¹,

John

2021

Heliyon

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In the present investigation, a totally of 673 newly designed 2,6-diphenyl piperidin-4-one derivatives are docked with 2B7N protein of Helicobacter pylori which causes peptic ulcer disease. The docking studies revealed that 2,6bis(3,4-dihydroxyphenyl)-3-phenethylpiperidin-4-one (BDPO) is identified as the most promising new compound with active nature against 2B7N with a binding affinity value of-8.0 Kcal/mol. The molecular structure of BDPO has been analyzed by DFT based theoretical calculations at the B3LYP/6-311þþG(d,p) level of theory using the Gaussian 16W program package. The molecular electrostatic potential, Frontier molecular energy gap, and Mulliken population analysis have been used to understand the reactive site of the molecule. The stability and hyper-conjugative interactions were studied by natural bond orbital analysis (NBO) based on a second-order perturbation approach. The thermodynamic properties like thermal energy, specific heat capacity, and entropy at different temperatures were also calculated. The calculated first-order hyper polarizability results show that the title compound is 25.3 times greater than that of standard reference material, urea. So the title molecule is a good non-linear material. Also, this molecule has Van der Waals attraction and steric effect. It undergoes local excitation for the first five excitations.

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“…Bacillus cereus and Salmonella typhimurium used in this study. and the standard drug reference of Regorafenib were evaluated using PreADMET [43] webserver.…”

Section: Biocidal Activitymentioning

confidence: 99%

Crystal structure, spectral investigations, DFT and antimicrobial activity of brucinium benzilate (BBA)

et al. 2021

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The unreported Brucinium Benzilate (BBA) crystal and hirshfeld surface analysis indicated the influence of intramolecular hydrogen bonding network. The protonation of tertiary nitrogen occurs as it is most basic. The protonated N-H + proton was observed at 7.08 ppm and the benzilate carbon COOat 178.41 ppm. Molecular electrostatic potential (MEP) studies indicated the electron-rich and electron-deficient sites in the molecule for understanding BBA interaction with an enzyme. Frontier molecular orbital (FMO) studies indicated that it is thermodynamically stable and HOMO-LUMO energy gap was found to be 4.454 eV. The highest interaction as the energy (322.86 kcal/mol) between tertiary ammonium N(LP) and H + . The compound showed the inhibition of Bacillus cereus and Salmonella typhimurium bacteria. ADMET properties indicated that BBA has drug characteristics in binding plasma protein.

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Synthesis, quantum chemical study, AIM simulation, in silico ADMET profile analysis, molecular docking and antioxidant activity assessment of aminofuran derivatives

Cited by 38 publications

References 52 publications

Substitution Effects on the Optoelectronic Properties of Coumarin Derivatives

Substitution Effects on the Optoelectronic Properties of Coumarin Derivatives

Design, docking, and DFT investigations of 2,6-bis(3,4-dihydroxyphenyl)-3-phenethylpiperidin-4-one

Crystal structure, spectral investigations, DFT and antimicrobial activity of brucinium benzilate (BBA)

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