Density functional theory calculations of spectral, NLO, reactivity, NBO properties and docking study of Vincosamide-N-Oxide active against lung cancer cell lines H1299

Mishra, Ashok Kumar; Tewari, S. P.

doi:10.1007/s42452-020-2842-9

Cited by 23 publications

(9 citation statements)

References 56 publications

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“…The three chromones studied in this work, C‐09 , C‐12 and C‐24 , present good performance compared to the NLOs of other materials. For example, all of them present their respective first hyperpolarizabilities at least 10 times larger than the theoretical values previously estimated using continuous solvation models for urea (

{ \approx 0.37 \times 10^{ - 30} }

esu), [62,63] and are comparable to those reported for p ‐nitroaniline (

{6.27 \times 10^{ - 30} }

esu [64] and

{8.86 \times 10^{ - 30} }

esu), [64] which are two standard NLO chromophores. These results suggest that the investigated chromones could have a possible use in photonics or optoelectronics.…”

Section: Resultssupporting

confidence: 60%

The Solute Polarization and Structural Effects on the Nonlinear Optical Response of Based Chromone Molecules

et al. 2023

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The solute polarization due to solvent is a an electrostatic quantum effect that impacts diverse molecular properties, including the nonlinear optical response of a material. An iterative procedure that allows updating the solute charge distribution in the presence of the solvent is combined with a sequential Monte Carlo/Quantum Mechanics methodology and Density Functional Theory methods to evaluate the nonlinear optical (NLO) response using the hyper Rayleigh scattering (HRS) of a series of chromones recently identified in Chamaecrista diphylla, an herbaceous plant abundant throughout the Americas and used in folk medicine. From this study, it is determined that from gas to solvent environment, the systems acquire low refractive index (n) and an improvement of the first hyperpolarizability (βHRS), signaling potential NLO uses. It is shown that the octupolar contributions (βJ=3) superate the dipolar ones (βJ=1) and dominate the second‐order optical response in both gas and liquid phases, which indicate nontrivial optical materials. Moreover, the solvent environment and structural changes in the periphery can tune significantly the dipolar/octupolar balance, showing a key to control the decoupling between these contributions.

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{ \approx 0.37 \times 10^{ - 30} }

esu), [62,63] and are comparable to those reported for p ‐nitroaniline (

{6.27 \times 10^{ - 30} }

esu [64] and

{8.86 \times 10^{ - 30} }

esu), [64] which are two standard NLO chromophores. These results suggest that the investigated chromones could have a possible use in photonics or optoelectronics.…”

Section: Resultssupporting

confidence: 60%

The Solute Polarization and Structural Effects on the Nonlinear Optical Response of Based Chromone Molecules

et al. 2023

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“…The GRPs are estimated via HOMO–LUMO energy values to predict the chemical nature of the molecules. A higher E HOMO value indicates a stronger electron donation tendency, whereas a lower value of E LUMO indicates a better ability to accept electrons. , According to Pearson, the molecules with a lower value of energy band gap ( E LUMO – E HOMO ) are soft and highly reactive in nature .…”

Section: Resultsmentioning

confidence: 99%

Theoretical Perspective toward Designing of 5-Methylbenzo [1,2-b:3,4-b′:6,5-b″] trithiophene-Based Nonlinear Optical Compounds with Extended Acceptors

Shafiq,

Mustafa,

Zahid

et al. 2023

ACS Omega

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A series of benzotrithiophene-based compounds (DCTM1-DCTM6) having D 1 -π 1 -D 2 -π 2 -A configuration were designed using a reference molecule (DCTMR) via incorporating pyrrole rings (n = 1−5) as the π-spacer (π 2 ). Quantum chemical calculations were performed to determine the impact of the pyrrole ring on the nonlinear optical (NLO) behavior of the above-mentioned chromophores. The optoelectronic properties of the compounds were determined at the MW1PW91/6-311G(d,p) functional. Among all of the derivatives, DCTM5 exhibited the least highest occupied molecular orbital−lowest unoccupied molecular orbital (HOMO−LUMO) band gap (E g ) 0.968 eV with a high softness of 0.562 eV −1 , and hence possessed the highest polarizability. Interestingly, transition density matrix (TDM) findings demonstrated that DCTM5 with an effective diagonal charge transmission proportion at the acceptor group supports the frontier molecular orbital (FMO) results. Additionally, the exciton binding energy values for DCTM1-DCTM6 were found to be less than that for DCTMR and thus, the effective charge transfer was examined in the derivatives. All of the derivatives exhibited effective NLO outcomes with the highest magnitude of linear polarizability ⟨α⟩, and first (β tot ) and second (γ tot ) hyperpolarizabilities relative to the parent compound. Nevertheless, the highest β tot and γ tot were obtained for DTCM1 and DTCM6, 7.0440 × 10 −27 and 22.260 × 10 −34 esu, respectively. Hence, through this structural tailoring with a pyrrole spacer, effective NLO materials can be obtained for optoelectronic applications.

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“…The higher the ICT, the lower the hardness and the lower the value of E g , implying that the ( 11 a – j ) has a high reactivity compared to ( 3 a – j ) [56] . This is due to the molecules′ increased ability to accept electrons more readily, which will most likely be reflected in their reactivity [57,58] . It should be noted, however, that while ICT and energy gap ( E g ) correlate with a molecule‘s chemical reactivity in general, they do not always reflect its biological activity, as the latter is dependent on a variety of other parameters and effects [59] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Characterization, Bioactivity Screening and Computational Studies of Diphenyl−malonohydrazides and Pyridines Derivatives

et al. 2023

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A series of new hydrazide (3 a-j) and pyridine (11 a-j) derivatives were synthesized using a convergent synthetic methodology by condensation of malono-di(2-phenylhydrazide) with arylidene malononitrile or arylidene ethyl cyanoacetate derivatives. The synthesized compounds (3, 11 a-j) were characterized using via IR, 1 H-, 13 C-NMR, and MS spectroscopies as well as elemental analysis. The biological activity of these molecules has been evaluated in vitro against two grampositive bacteria (Staphylococcus aureus and Streptococcus pneumoniae) and one-gram negative bacteria (Escherichia coli), as well as one fungus (Candida albicans). The results of the bioactive assay revealed that the synthesized pyridine (11 a-j) derivatives had greater antibacterial efficacy than the hydrazide (3 a-j) derivatives and were comparable to the reference drug Augmentin. Furthermore, docking studies against the Staphylococcus aureus dihydrofolate reductase (DHFR) protein revealed that pyridine derivatives (11 a-j) had higher binding interactions affinity (ΔG = À 9.59 ∼ À 7.69 kcal/mol) than diphenylÀ malonohydrazide derivatives (3 a-j), which achieved a binding affinity in the range of (ΔG = À 9.65 ∼ À 6.77 kcal/ mol), supporting the experimental results. Finally, DFT and TD-DFT were used to gain a better understanding of the structureactivity relationship and biological activity of the new synthesized hydrazide/pyridine derivatives.

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Density functional theory calculations of spectral, NLO, reactivity, NBO properties and docking study of Vincosamide-N-Oxide active against lung cancer cell lines H1299

Cited by 23 publications

References 56 publications

The Solute Polarization and Structural Effects on the Nonlinear Optical Response of Based Chromone Molecules

The Solute Polarization and Structural Effects on the Nonlinear Optical Response of Based Chromone Molecules

Theoretical Perspective toward Designing of 5-Methylbenzo [1,2-b:3,4-b′:6,5-b″] trithiophene-Based Nonlinear Optical Compounds with Extended Acceptors

Synthesis, Characterization, Bioactivity Screening and Computational Studies of Diphenyl−malonohydrazides and Pyridines Derivatives

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