Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach

Satheeshkumar, Rajendran; Sayın, Koray; Kaminsky, Werner; Prasad, K. J. Rajendra

doi:10.1007/s00706-017-2050-5

Cited by 8 publications

(3 citation statements)

References 25 publications

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“…In previous research, the carbon NMR chemical shifts were observed between ∼110‐160 ppm and simulated in ∼120‐ 170 ppm, depending on the bonded atom or/and substituent group around the ring system. Also, it has been reported that the 13 C NMR shifts for the carbon atoms next to an electronegative atom, such as N, O and F atoms, were observed in 180–200 ppm, because the higher electronegative atom that is next to the nucleus of the carbon lowers the electron cloud around the carbon nucleus and causes higher chemical shifts.…”

Section: Resultsmentioning

confidence: 99%

A DFT Investigation on the Structure, Spectroscopy (FT‐IR and NMR), Donor‐Acceptor Interactions and Non‐Linear Optic Properties of (±)‐1,2‐Dehydroaspidospermidine

Uludag

Serdaroğlu

2019

ChemistrySelect

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In this study, (±)‐1,2‐Dehydroaspidospermidine was analyzed by elemental analysis, 1H and 13C NMR, and FT‐IR spectra. Also, because the starting geometry is essential to evaluate the structural, electronic, and spectral properties of this compound, we used the potential energy surface (PES) scan by the B3LYP/6‐31G(d,p) hybrid functional to determine the stable structures of the (±)‐1,2‐Dehydroaspidospermidine. Thus, three stable conformations of the compound were used in all of the electronic and spectroscopic simulations performed by the M06‐2X, G96LYP, and B3LYP functionals at the 6–311++G(d,p) basis set in a vacuum and chloroform. After the observed and simulated FT‐IR and NMR data were compared, the second order perturbative theory in the NBO (Natural Bond Orbital) basis was used to interpret the critical donor‐acceptor interactions; the dominant contribution to the lowering of the second order energy for all conformers was the π→ π* and σ→ π* interactions. Also, we used both NLO (Non Linear Optic) and FMO (Frontier Molecular Orbital) analyses to investigate the non‐linear optical property and the biochemical reactivity of the compound. The results of this work demonstrated that the compound has an available non‐linear optical property (β=6.62 x 10−30 esu) that can be used in optoelectronic technology, and, besides, it has biological activity because of its strong intramolecular interactions.

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Section: Resultsmentioning

confidence: 99%

A DFT Investigation on the Structure, Spectroscopy (FT‐IR and NMR), Donor‐Acceptor Interactions and Non‐Linear Optic Properties of (±)‐1,2‐Dehydroaspidospermidine

Uludag

Serdaroğlu

2019

ChemistrySelect

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“…The energy differential between LUMO and HOMO is a key metric used to measure the biological activity feature. [20]. Energy differential between LUMO and HOMO is a key metric used to measure the biological activity characteristic.…”

Section: Molecular Reactivitymentioning

confidence: 99%

Investigation of Anticancer Properties of 2-benzylidene-1-indanone and Its Derivatives by DFT and Molecular Docking

Alkaya Yıldız,

Erkan

2024

Turkish Computational and Theoretical Chemistry

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In this study, 2-benzylidene-1-indanone and its derivatives, which is a chalcone compound and contains indanone in its structure, were examined. Quantum chemical parameters for these compounds were calculated with the B3LYP method and the 6-31G(d) basis set and evaluated for their biological activity. The effect of different functional groups (F, Cl, Br, CF3, CH3 and OCH3) attached to the 2-benzylidene-1-indanone compound on biological activity was investigated. Some quantum chemical parameters such as highest energy filled molecule orbital energy (EHOMO), lowest non-bonding empty molecule orbital energy (ELUMO), energy gap (ΔE), hardness (η), softness (σ), global molecular electrophilicity (ω) index, global molecular nucleophilicity (ɛ) index, electron-accepting (ω+) and electron-donating (ω-) electrophilicity index were calculated for the biological activities of the compounds. Frontier molecular orbitals and molecular electrostatic potential (MEP) maps were interpreted. The biological activities of 2-benzylidine-1-indanone and some of its derivatives bearing the 1-indanone skeleton were evaluated by performing molecular docking studies with the target protein PDB ID = 1HJD corresponding to the melanoma cell line. The activity ranking obtained with quantum chemical parameters was found to be compatible with the binding energies obtained from docking results.

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“…Based on the above insight, quinoline derivatives were developed by condensing 2-aminoarylketones with carbonyl compounds owning a reactive methylene group, followed by cyclodehydration. Quantum chemical calculations were conducted at the B3LYP/6-311G(d,p), CAM-B3LYP/6-311G(d,p), and M06-2X/6-311G(d,p) levels of theory in the gas phase to optimize the structure, determine vibrational frequencies, chemical shift values using NMR analysis, Hirshfeld surface analysis, highest occupied molecular orbital (HOMO)/lowest unoccupied molecular orbital (LUMO), molecular electrostatic potential (MEP) maps, nonlinear optical (NLO) properties, and thermodynamic properties. − Here, we would like to report a convenient and straightforward workup method for the synthesis of quinoline molecule ( 3 ) using freshly prepared polyphosphoric acid (PPA) − (P 2 O 5 in H 3 PO 4 ) under solvent-free conditions from 2-aminobenzophenone ( 1 ) and pentan-2,3-dione ( 2 ) through Friedländer quinoline synthesis.…”

Section: Introductionmentioning

confidence: 99%

Enhanced Method for the Synthesis and Comprehensive Characterization of 1-(4-Phenylquinolin-2-yl)propan-1-one

Rajendran,

Montecinos,

Cisterna

et al. 2023

ACS Omega

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We present an enhanced method for synthesizing a novel compound, 1-(4-phenylquinolin-2-yl)propan-1-one (3), through the solvent-free Friedlander quinoline synthesis using poly(phosphoric acid) as an assisting agent. The crystal structure of compound 3 is analyzed using FT-IR, and the chemical shifts of its 1 H-and 13 C NMR spectra are measured and calculated using B3LYP/6-311G(d,p), CAM-B3LYP/6-311G(d,p), and M06-2X/6-311G(d,p) basis sets in the gas phase. Additionally, the optimized geometry of quinoline 3 is compared with experimental X-ray diffraction values. Through density functional theory calculations, we explore various aspects of the compound's properties, including noncovalent interactions, Hirshfeld surface analysis, nonlinear optical properties, thermodynamic properties, molecular electrostatic potential, and frontier molecular orbitals. These investigations reveal chemically active sites within this quinoline derivative that contribute to its chemical reactivity.

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Synthesis, spectroscopic, in vitro cytotoxicity and crystal structures of novel fluorinated dispiroheterocycles: DFT approach

Cited by 8 publications

References 25 publications

A DFT Investigation on the Structure, Spectroscopy (FT‐IR and NMR), Donor‐Acceptor Interactions and Non‐Linear Optic Properties of (±)‐1,2‐Dehydroaspidospermidine

A DFT Investigation on the Structure, Spectroscopy (FT‐IR and NMR), Donor‐Acceptor Interactions and Non‐Linear Optic Properties of (±)‐1,2‐Dehydroaspidospermidine

Investigation of Anticancer Properties of 2-benzylidene-1-indanone and Its Derivatives by DFT and Molecular Docking

Enhanced Method for the Synthesis and Comprehensive Characterization of 1-(4-Phenylquinolin-2-yl)propan-1-one

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