Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Premkumar, S.; Jawahar, Ajay; Mathavan, T.; Dhas, M. Kumara; Benial, A. Milton Franklin

doi:10.1016/j.saa.2014.11.029

Cited by 49 publications

(18 citation statements)

References 37 publications

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“…Bonding and antibonding interactions were analyzed qualitatively using NBO analysis. Perturbation energies E (2) were given using equation :

normalE ((), 2) = ΔEij = qi \frac{{((), F_{i, j})}^{2}}{(E_{j} - E_{i})}

where F i,j off‐diagonal matrix element of NBO q i occupancy of donor orbital and E i and E j diagonal elements. …”

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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“…Bonding and antibonding interactions were analyzed qualitatively using NBO analysis. Perturbation energies E (2) were given using equation :

normalE ((), 2) = ΔEij = qi \frac{{((), F_{i, j})}^{2}}{(E_{j} - E_{i})}

where F i,j off‐diagonal matrix element of NBO q i occupancy of donor orbital and E i and E j diagonal elements. …”

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

2020

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“…The three-dimensional structure (3D) of chlorpyrifos was downloaded from the ChemSpider database and the B3LYP/6-31G** level was used with Gaussian 09 (Lomas, 2014;Premkumar et al, 2015). Figure 2(b) and (c) shows the HOMO and LUMO orbits of chlorpyrifos using the Multiwfn program (Lu & Chen, 2012).…”

Section: Resultsmentioning

confidence: 99%

“…The initial model of the chlorpyrifos was extracted from the ChemSpider database. Geometric optimization of the chlorpyrifos was conducted at the B3LYP/6-31G** level using Gaussian 09 (Lomas, 2014;Premkumar, Jawahar, Mathavan, Kumara Dhas, & Milton Franklin Benial, 2015).…”

Section: System Preparationmentioning

confidence: 99%

Exploration of the chlorpyrifos escape pathway from acylpeptide hydrolases using steered molecular dynamics simulations

Wang¹,

Jin²,

Wang³

et al. 2015

Journal of Biomolecular Structure and Dynamics

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Acylpeptide hydrolases (APH) catalyze the removal of an N-acylated amino acid from blocked peptides. APH is significantly more sensitive than acetylcholinesterase, a target of Alzheimer's disease, to inhibition by organophosphorus (OP) compounds. Thus, OP compounds can be used as a tool to probe the physiological functions of APH. Here, we report the results of a computational study of molecular dynamics simulations of APH bound to the OP compounds and an exploration of the chlorpyrifos escape pathway using steered molecular dynamics (SMD) simulations. In addition, we apply SMD simulations to identify potential escape routes of chlorpyrifos from hydrolase hydrophobic cavities in the APH-inhibitor complex. Two previously proposed APH pathways were reliably identified by CAVER 3.0, with the estimated relative importance of P1 > P2 for its size. We identify the major pathway, P2, using SMD simulations, and Arg526, Glu88, Gly86, and Asn65 are identified as important residues for the ligand leaving via P2. These results may help in the design of APH-targeting drugs with improved efficacy, as well as in understanding APH selectivity of the inhibitor binding in the prolyl oligopeptidase family.

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“…The interaction between the donor and acceptor molecular bonds gives a helpful basis set for exploring the charge exchange interaction in the molecule frameworks [34]. NBO investigation of DBT is performed at the DFT/B3LYP/6-311++G (d, p) level of basis set and the calculated values are recorded in Table 8.…”

Section: Natural Bond Orbital Analysismentioning

confidence: 99%

Structural, Spectroscopic Investigation and Binding Mechanism of 2,5-dibromotoluene With Human Serum Albumin

Subbiah¹,

Muthusamy²,

Murugan³

2021

Preprint

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The optimized structure, comparative theoretical and experimental vibrational assignments of 2,5-dibromotoluene (DBT) have been evaluated by density functional theory (DFT) with higher basis set calculations. The global reactivity determination such as energy gap, dipole moment has been explored. The locale reactive sites of the molecule are described by applying the electrostatic potential. The interactions between the bonds are assessed by the natural bond orbital (NBO) investigation. The resonance quality 1H and13C (NMR) shifts of the molecule calculated by GIAO method. Optical transparency of the molecule has been analyzed by theoretical UV-Visible spectra. The binding of toluene with serum albumin protein utilizing in silico has been validated and subsequently, the present work clears the method for scheming the drugs in the dealing of serum albumin.

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Vibrational spectroscopic and DFT calculation studies of 2-amino-7-bromo-5-oxo-[1]benzopyrano [2,3-b]pyridine-3 carbonitrile

Cited by 49 publications

References 37 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

Exploration of the chlorpyrifos escape pathway from acylpeptide hydrolases using steered molecular dynamics simulations

Structural, Spectroscopic Investigation and Binding Mechanism of 2,5-dibromotoluene With Human Serum Albumin

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