6-Aminocoumarin-Naphthoquinone Conjugates: Design, Synthesis, Photophysical and Electrochemical Properties and DFT Calculations

Miranda, Fabio S.; Ronconi, Célia M.; Sousa, Mikaelly O. B.; Silveira, Gleiciani Q.; Vargas, Maria D.

doi:10.5935/0103-5053.20130279

Cited by 7 publications

(6 citation statements)

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“…The participation of nonbonded electrons was assessed through NBO analysis at the same level of the geometry optimization. , …”

Section: Theoretical Methodsmentioning

confidence: 99%

“…41,42 The participation of nonbonded electrons was assessed through NBO analysis 43 at the same level of the geometry optimization. 44,45 To minimize the ΔA iso values in relation to coupling constants, J, as well as the chemical shift variation, Δδ, response surfaces (RS) and Counter's graph (CG) were employed. The Response surfaces is a chemometric method that involves the development of a surface for the J and Δδ variation and the minimization of the ΔA iso response.…”

Section: Theoretical Methodsmentioning

confidence: 99%

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Value of NMR Parameters and DFT Calculations for Quantum Information Processing Utilizing Phosphorus Heterocycles

Lino

Rocha²,

Ramalho

2017

J. Phys. Chem. A

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Quantum computing is the field of science that uses quantum-mechanical phenomena, such as superposition and entanglement, to perform operations on data. The fundamental information unit used in quantum computing is the quantum bit or qubit. It is well-known that quantum computers could theoretically be able to solve problems much more quickly than any classical computers. Currently, the first and still the most successful implementations of quantum information processing (QIP) have been based on nuclear spins in liquids. However, molecules that enable many qubits NMR QIP implementations should meet some conditions: have large chemical shifts and be appropriately dispersed for qubit addressability, appreciable spin-spin coupling between any pair of spins, and a long relaxation time. In this line, benzyldene-2,3-dihydro-1H-[1,3]diphosphole (BDF) derivatives have been theoretically tested for maximizing large chemical shifts, spin-spin coupling, and minimizing the hyperfine coupling constant. Thus, the structures were optimized at the B3LYP/6-311G(d,p) level and showed a significant similarity with the experimental geometrical parameters. The NMR spectroscopic parameters (δ and J) were calculated with six different DFT functionals. The τ-HCTH/6-31G(2d) level is in better agreement with the experimental data of P andC chemical shifts, while PCM-B3LYP/cc-pVDZ level shows a decrease on deviation between calculated and experimental values for P-P and P-C SSCC. The surface response technique was employed to rationalize how the hyperfine constant varies with the chemical shifts and coupling constants values. From our findings, BDF-NO was the best candidate for NMR quantum computations (NMR-QC) among the studied series.

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“…The participation of nonbonded electrons was assessed through NBO analysis at the same level of the geometry optimization. , …”

Section: Theoretical Methodsmentioning

confidence: 99%

Section: Theoretical Methodsmentioning

confidence: 99%

Value of NMR Parameters and DFT Calculations for Quantum Information Processing Utilizing Phosphorus Heterocycles

Lino

Rocha²,

Ramalho

2017

J. Phys. Chem. A

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“…31 (Table 1). On the other hand, the CAM-B3LYP and ωB97XD long-range hybrid functional [32][33][34][35] showed higher error values, -52.87 nm and -54.75 nm, respectively. e PBE meta-GGA functional showed an error value of 78.82 nm, the highest error for the spectroscopic properties (Table 1).…”

Section: Selection Of the Dft Functional For Spectroscopicmentioning

confidence: 92%

Detection of Chemical Weapon Agents Using Spectroscopic Probes: A Computational Study

Braga

Silva

Mancini

et al. 2020

Journal of Chemistry

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Organophosphorus compounds are organic compounds widely employed in agriculture as well as in chemical weapons. The use in agriculture is due to their insecticidal properties. However, in chemical warfare, the use of organophosphorus is associated with acetylcholinesterase inhibition, which promotes the cholinergic syndromes. In this line, the fast detection of this class of compound is crucial for the determination of environmental exposure. This improved detection will naturally allow for more prompt courses of treatment depending on the contaminant findings. In this perspective, the dipyrrinone oxime (1) was employed for the detection of organophosphorus compounds that are employed as nerve agents, such as cyclosarin, sarin, soman, diethyl chlorophosphate, diisopropylfluorophosphate, 2-(dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate, O-ethyl-S-[2-(diethylamino)ethyl]methylphosphonothioate, O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothioate, and O,O-diethyl-S-[2-(diethylamino)ethyl] phosphorothioate, through fluorescent emission. The thermodynamics and kinetic parameters as well as spectroscopic properties of the complexes formed for 1 and all organophosphorus compounds previously cited were investigated by means of theoretical calculations. From our findings, only the diethyl chlorophosphate, 2-(dimethylamino)ethyl N,N-dimethylphosphoramidofluoridate, and O,O-diethyl-S-[2-(diethylamino)ethyl] phosphorothioate emitted fluorescence in the hexane, toluene, chloroform, dichloromethane, methanol, acetonitrile, water, and dimethyl sulfoxide solvents. The study of the absorption wavelength with the most polar solvent showed higher values compared to apolar solvents. In the same solvent, for instance, soman in hexane showed the lowest absorption wavelength value, 324.5 nm, and DCP the highest value, 330.8 nm. This behavior was observed in other tested solvents. The thermodynamic parameters indicate negative Gibbs free energy (ΔG) values for the O-ethyl-S-[2(diisopropylamino)ethyl] methylphosphonothioate with 1 reaction. On the other hand, the sarin and cyclosarin revealed the lowest Gibbs free energy (ΔG‡) values, being kinetically favorable and presenting more reactivity.

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“…With the help of the DFT calculations, the optimized geometry of each molecule was generated and the localization of electron density on HOMO and LUMO of the 2-deoxy-D-ribose (2DR), 2-deoxy-glucose (2DAG) and 2-deoxy-D-glucose (2DG) were determined in the gaseous state and in water as a solvent, as shown in Figure 2 [58][59][60]. Furthermore, for studying the stability of these molecules, thermodynamic properties such free energy, thermal energy, zero-point energy, optimization energy and the dipole moment in gaseous as well as in aqueous solution at 300 K were calculated.…”

Section: Dft Calculationsmentioning

confidence: 99%

In Silico Evaluation of Binding of 2-Deoxy-D-Glucose with Mpro of nCoV to Combat COVID-19

et al. 2022

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COVID-19 has threatened the existence of humanity andthis infection occurs due to SARS-CoV-2 or novel coronavirus, was first reported in Wuhan, China. Therefore, there is a need to find a promising drug to cure the people suffering from the infection. The second wave of this viral infection was shaking the world in the first half of 2021. Drugs Controllers of India has allowed the emergency use of 2-deoxy-D-glucose (2DG) in 2021 for patients suffering from this viral infection. The potentiality of 2-deoxy-D-glucose to intervene in D-glucose metabolism exists and energy deprivation is an effective parameter to inhibit cancer cell development. Once 2DG arrives in the cells, it becomes phosphorylated to 2-deoxy-D-glucose-6-phosphate (2-DG6P), a charged molecule expressively captured inside the cells. On the other hand, 2DG lacks the ability to convert into fructose-6-phosphate, resulting in a hampering of the activity of both glucose-6-phosphate isomerase and hexokinase, and finally causing cell death. Hence, the potential and effectiveness of 2DG with the main protease (Mpro) of novel coronavirus (nCoV) should be investigated using the molecular docking and molecular dynamics (MD) simulations. The ability of 2DG to inhibit the Mpro of nCoV is compared with 2-deoxyglucose (2DAG), an acyclic molecule, and 2-deoxy-D-ribose (2DR). The binding energy of the molecules with the Mpro of nCoV is calculated using molecular docking and superimposed analysis data is obtained. The binding energy of 2DG, 2DR and 2DAG was −2.40, −2.22 and −2.88 kcal/mol respectively. Although the molecular docking does not provide reliable information, therefore, the binding affinity can be confirmed by molecular dynamics simulations. Various trajectories such as Rg, RMSD, RMSF, and hydrogen bonds are obtained from the molecular dynamics (MD) simulations. 2DG was found to be a better inhibitor than the 2DAG and 2DR based on the results obtained from the MD simulations at 300 K. Furthermore, temperature-dependent MD simulations of the Mpro of nCoV with promising 2DG was performed at 295, 310 and 315 K, and the effective binding with the Mpro of nCoV occurred at 295 K. With the use of DFT calculations, optimized geometry and localization of electron density of the frontier molecular orbitals were calculated.

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6-Aminocoumarin-Naphthoquinone Conjugates: Design, Synthesis, Photophysical and Electrochemical Properties and DFT Calculations

Cited by 7 publications

References 1 publication

Value of NMR Parameters and DFT Calculations for Quantum Information Processing Utilizing Phosphorus Heterocycles

Value of NMR Parameters and DFT Calculations for Quantum Information Processing Utilizing Phosphorus Heterocycles

Detection of Chemical Weapon Agents Using Spectroscopic Probes: A Computational Study

In Silico Evaluation of Binding of 2-Deoxy-D-Glucose with Mpro of nCoV to Combat COVID-19

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