scholarly journals Glutarimides: Biological activity, general synthetic methods and physicochemical properties

2015 ◽  
Vol 69 (5) ◽  
pp. 523-536
Author(s):  
Jelena Popovic-Djordjevic ◽  
Vesna Vitnik ◽  
Zeljko Vitnik ◽  
Milovan Ivanovic
Keyword(s):  
Molecular Electrostatic Potential ◽  
Energy Gap ◽  
Dicarboxylic Acids ◽  
Synthetic Methods ◽  
Frontier Molecular Orbital ◽  
Geometrical Parameters ◽  
Oxidation Reactions ◽  
Reductase Inhibitors ◽  
Imide Ring ◽  
Ft Ir

Glutarimides, 2,6-dioxopiperidines are compounds that rarely occur in natural sources, but so far isolated ones exert widespread pharmacological activities, which makes them valuable as potential pharmacotherapeutics. Glutarimides act as androgen receptor antagonists, anti-inflammatory, anxiolytics, antibacterials, and tumor suppressing agents. Some synthetic glutarimide derivatives are already in use as immunosuppressive and sedative (e.g., thalidomide) or anxiolytics (buspirone) drugs. The wide applicability of this class of compounds, justify the interest of scientists to explore new pathways for its syntheses. General methods for synthesis of six-membered imide ring, are presented in this paper. These methods include: a) reaction of dicarboxylic acids with ammonia or primary amine, b) reactions of cyclization: amido-acids, diamides, dinitriles, nitrilo-acids, amido-nitriles, amido-esters, amidoacyl-chlorides or diacyl-chlorides, c) adition of carbon-monoxide on a,b-unsaturated amides, d) oxidation reactions, e) Michael adition of active methylen compounds on methacrylamide or conjugated amides. Some of the described methods are used for closing glutarimide ring in syntheses of farmacological active compounds sesbanimide and aldose reductase inhibitors (ARI). Analyses of the geometry, as well as, the spectroscopic analyses (NMR and FT-IR) of some glutarimides are presented because of their broad spectrum of pharmacological activity. To elucidate structures of glutarimides, geometrical parameters of newly synthesized tert-pentyl-1-benzyl-4-methyl-glutarimide-3-carboxylate (PBMG) are analyzed and compared with the experimental data from X-ray analysis for glutarimide. Moreover, molecular electrostatic potential (MEP) surface which is plotted over the optimized geometry to elucidate the reactivity of PBMG molecule is analyzed. The electronic properties of glutarimide derivatives are explained on the example of thalidomide. The Frontier Molecular Orbital (FMO) and their energies are presented, as well as the energy gap between them.

scholarly journals Synthesis, crystal and molecular structure, vibrational spectroscopic, DFT study and activity evaluation of 4-(2-chlorobenzyl)-1-(4-hydroxy -3-((4-hydroxypiperidin-1-yl)methyl-5-methoxyphenyl)-[1,2,4] triazolo[4,3-a]quinazolin-5(4H)-one

2021 ◽  
Author(s):  
Qingmei Wu ◽  
Wenjun Ye ◽  
Qian Guo ◽  
Tianhui Liao ◽  
Weike Liao ◽  
...  
Keyword(s):  
Molecular Structure ◽  
Title Compound ◽  
Density Functional ◽  
Frontier Molecular Orbital ◽  
Geometrical Parameters ◽  
X Ray Diffraction ◽  
Mannich Reactions ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ft Ir

In current work, we have firstly synthesized 4-(2-chlorobenzyl)-1-(4-hydroxy-3- ((4-hydroxypiperidin-1-yl)methyl)-5-methoxyphenyl)-[1,2,4]triazolo[4,3-a]quinazolin-5(4H)-one (1) by ring-opening, cyclization, substitution, doamine condensation and Mannich reactions. The structural properties of the title compound 1 were explored using spectroscopy (1H NMR, 13C NMR, MS and FT-IR) and X-ray crystallography method. The single-crystal structure confirmed by X-ray diffraction was consistent with the molecular structure optimized by density functional theory (DFT) calculation at B3LYP/6-311G (2d, p) level of theory. The geometrical parameters, molecular electrostatic potential (MEP) and frontier molecular orbital (FMO) analysis were performed by DFT using the B3LYP/6-311G (2d, p) method. Molecular docking has shown favorable interaction between the title compound 1 and SHP2 protein. The inhibitory activity of target compound 1 on SHP2 protein at 10 μM is better than the reference compound (SHP244).

scholarly journals Molecular structure, electronic properties, vibrational analysis and reactivity parameters Of (Z)-N-(4-methoxyphenyl)-2-(4-oxothiazolidin-2-ylidene)acetamide: a theoretical study

2019 ◽  
Vol 9 (4) ◽  
pp. 4150-4156
Keyword(s):  
Electrostatic Potential ◽  
Molecular Electrostatic Potential ◽  
Energy Gap ◽  
Vibrational Analysis ◽  
Basis Sets ◽  
Frontier Molecular Orbital ◽  
Dft Methods ◽  
Potential Surfaces ◽  
Long Time ◽  
Homo And Lumo

Thiazolidine having important medicinal properties have been under investigation for a long time. In a recent study, A. Galushchinskiy et. al. synthesized and studied the crystal structure of thiazolidine derivative (Z)-N-(4-Methoxyphenyl)-2-(4-oxothiazolidin-2- ylidene)acetamide (MPOA). Keeping biological activity of thiazolidine in mind, quantum chemical calculations of energies, geometrical structure and vibrational wave numbers were carried out by DFT methods with 6-311++G(d,p) basis sets. A study on the electronic, dipole moment and frontier molecular orbital energies were also performed. HOMO and LUMO energy gap confirm the occurring of charge transformation in the molecule. The Frontier Molecular Orbital’s (FMO), Molecular Electrostatic Potential were studied. The theoretical IR for the title compound has been also calculated. Molecular electrostatic potential surfaces and various reactivity parameters have also been studied to explain the reactive nature of compound.

scholarly journals Crystal Structure, Spectral investigations, DFT and Antimicrobial activity of Brucinium Benzilate (BBA)

2021 ◽  
Author(s):  
Karnan Chandran ◽  
Nagaraja Karachalacherevu Seetharamiah ◽  
Manivannan Sambanthan ◽  
Manikandan Anandhan ◽  
Ragavendran Venkatesan
Keyword(s):  
Molecular Electrostatic Potential ◽  
Energy Gap ◽  
Intramolecular Hydrogen Bonding ◽  
Frontier Molecular Orbital ◽  
Lumo Energy ◽  
Ammonium N ◽  
Intramolecular Hydrogen ◽  
Homo Lumo ◽  
Binding Plasma Protein ◽  
Tertiary Nitrogen

Abstract 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 COO- at 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.

scholarly journals FT-IR, FT-Raman, NMR Spectroscopic and DFT Quantum Chemical Investigations of 6-Methylcoumarin

2021 ◽  
Vol 33 (11) ◽  
pp. 2715-2722
Author(s):  
R. Kanimozhi ◽  
V. Arjunan
Keyword(s):  
Natural Bond Orbital ◽  
Energy Gap ◽  
Basis Sets ◽  
Frontier Molecular Orbital ◽  
Vibrational Assignments ◽  
B3lyp Method ◽  
Ft Ir ◽  
High Level ◽  
Orbital Analysis ◽  
Ft Raman

The structural geometry, electronic and reactivity characteristics, vibrational assignments and the fundamental modes of 6-methylcoumarin have been carried out. The effect of methyl group on the pyrone skeletal vibrations was also discussed. The experimental vibrational frequencies were compared with the wavenumbers obtained theoretically from the B3LYP method employing the high level 6-311++G** and cc-pVTZ basis sets. Frontier molecular orbital (FMO) energy and the LUMO-HOMO energy gap was measured. The atomic charges and the bond properties were examined by natural bond orbital analysis. The hydrogen and carbon environment were examined by NMR spectra. The nuclophilic, electrophilic and free radical attacking sites of 6-methylcoumarin were also analyzed.

Preparation, Characterization and Structure Prediction of In2SnO3 and Spectroscopic (FT-IR, FT-Raman, NMR and UV-Visible) Study Using Computational Approach

2019 ◽  
Vol 19 (6) ◽  
pp. 3511-3518 ◽  
Author(s):  
R Perumalsamy ◽  
K Kaviyarasu ◽  
S Nivetha ◽  
A Ayeshamariam ◽  
N Punithavelan ◽  
...  
Keyword(s):  
Structure Prediction ◽  
Sol Gel ◽  
Bulk Phase ◽  
Frontier Molecular Orbital ◽  
Geometrical Parameters ◽  
Frequency Pattern ◽  
Ft Ir ◽  
Uv Visible ◽  
Periodic Arrangement ◽  
Ft Raman

Unadulterated and scorch stage In2SnO3 nanopowder is effectively arranged with the doping proportion of 80–20% (In2O3–Sn) by simple sol–gel combustion direction. The material is characterized by XRD measurements and their geometrical parameters are compared with calculated values. The FT-IR and NMR spectra are recorded in both bulk and nanophase and FT-Raman spectrum is recorded in bulk phase and the fundamental frequencies are assigned. The optimized parameters and the frequencies are calculated using HF and DFT (B3LYP, B3PW91 and MPW1PW91) theory in bulk phase of In2SnO3 and are compared with its nanophase. The vibrational frequency pattern in nanophase gets realigned and the frequencies are shifted up and down little bit to the region of spectra when compared with bulk phase. The UV-visible spectrum is simulated and analyzed. The frontier molecular orbital analysis has been carried out and the values of the HOMO-LUMO bandgap (Kubo gap) explore the optical and electronic characteristics of the In2SnO3. Structural studies by XRD showed the crystallite sizes of the particles. The atomic arrangement in the grain boundary seems to be somewhat different from regular periodic arrangement whereas inside the grain there is a good periodic arrangement of atoms. Above 10 mol% Sn ions, 15 mol% Sn ions, 20 mol% Sn ions to 50 mol% Sn ions form correlated clusters, 20 mol% Sn ions which lead to broadening. These EPR spectra were formed to contain two different components, one from the single isolated ions and the other from the clusters. The transition is observed for different composition increase with decreasing grain size.

scholarly journals Synthetic, Mesomorphic, and DFT Investigations of New Nematogenic Polar Naphthyl Benzoate Ester Derivatives

Materials ◽  
2021 ◽  
Vol 14 (10) ◽  
pp. 2587
Author(s):  
Salma A. Al-Zahrani ◽  
Hoda A. Ahmed ◽  
Mohamed A. El-atawy ◽  
Khulood A. Abu Al-Ola ◽  
Alaa Z. Omar
Keyword(s):  
Density Functional ◽  
Energy Gap ◽  
Molecular Structures ◽  
Experimental Investigations ◽  
Geometrical Parameters ◽  
Polar Group ◽  
Scanning Calorimetry ◽  
Structural Shape ◽  
Elemental Analyses ◽  
Ft Ir

Four new non-symmetrical derivatives based on central naphthalene moiety, 4-((4–(alkoxy)phenyl) diazenyl)naphthalen–1–yl 4–substitutedbenzoate (In/x), were prepared, and their properties were investigated experimentally and theoretically. The synthesized materials bear two wing groups: an alkoxy chain of differing proportionate length (n = 6 and 16 carbons) and one terminal attached to a polar group, X. Their molecular structures were elucidated via elemental analyses and FT-IR and NMR spectroscopy. Differential scanning calorimetry (DSC) and polarized optical microscopy (POM) were carried out to evaluate their mesomorphic properties. The results of the experimental investigations revealed that all the synthesized analogues possess only an enantiotropic nematic (N) mesophase with a high thermal stability and broad range. Density functional theory (DFT) calculations were in accordance with the experimental investigations and revealed that all prepared materials are to be linear and planar. Moreover, the rigidity of the molecule increased when an extra fused ring was inserted into the center of the structural shape, so its thermal and geometrical parameters were affected. Energy gap predictions confirmed that the I16/c derivative is more reactive than other compounds.

scholarly journals X-ray diffraction and Density Functional Theory based structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-1,2,4-triazolone

2021 ◽  
Vol 12 (4) ◽  
pp. 459-468
Author(s):  
Shilpa Mallappa Somagond ◽  
Ahmedraza Mavazzan ◽  
Suresh Fakkirappa Madar ◽  
Madivalagouda Sannaikar ◽  
Shankar Madan Kumar ◽  
...  
Keyword(s):  
Density Functional Theory ◽  
Density Functional ◽  
Energy Gap ◽  
Basis Set ◽  
Frontier Molecular Orbital ◽  
Geometrical Parameters ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Functional Theory ◽  
X Ray

This study is composed of X-ray diffraction and Density Functional Theory (DFT) based molecular structural analyses of 2-phenyl-4-(prop-2-yn-1-yl)-2,4-dihydro-3H-1,2,4-triazol-3-one (2PPT). Crystal data for C11H9N3O: Monoclinic, space group P21/c (no. 14), a = 7.8975(2) Å, b = 11.6546(4) Å, c = 11.0648(3) Å, β = 105.212(2)°, V = 982.74(5) Å3, Z = 4, T = 296.15 K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.346 g/cm3, 13460 reflections measured (5.174° ≤ 2Θ ≤ 64.72°), 3477 unique (Rint = 0.0314, Rsigma = 0.0298) which were used in all calculations. The final R1 was 0.0470 (I > 2σ(I)) and wR2 was 0.1368 (all data). The experimentally determined data was supported by theoretically optimized calculations processed with the help of Hartree-Fock (HF) technique and Density Functional Theory with the 6-311G(d,p) basis set in the ground state. Geometrical parameters (Bond lengths and angles) as well as spectroscopic (FT-IR, 1H NMR, and 13C NMR) properties of 2PPT molecule has been optimized theoretically and compared with the experimentally obtained results. Hirshfeld surface analysis with 2D fingerprinting plots was used to figure out the possible and most significant intermolecular interactions. The electronic characterizations such as molecular electrostatic potential map (MEP) and Frontier molecular orbital (FMO) energies have been studied by DFT/B3LYP approach. The MEP imparted the detailed information regarding electronegative and electropositive regions across the molecule. The HOMO-LUMO energy gap as high as 5.3601 eV was found to be responsible for the high kinetic stability of the 2PPT.

scholarly journals New nematogenic conical-shaped supramolecular H-bonded complexes for solar energy investigations

2021 ◽  
Vol 11 (1) ◽  
Author(s):  
Sobhi M. Gomha ◽  
Hoda A. Ahmed ◽  
Mohamed Shaban ◽  
Tariq Z. Abolibda ◽  
Khalid Abdulaziz Alharbi ◽  
...  
Keyword(s):  
Solar Energy ◽  
Density Functional ◽  
Geometrical Structure ◽  
Energy Gap ◽  
Supramolecular Complexes ◽  
Geometrical Parameters ◽  
Scanning Calorimetry ◽  
Functional Theory ◽  
Ft Ir ◽  
Flexible Core

AbstractNew conical-shaped geometrical supramolecular H-bonded liquid crystal complexes were formed through 1:2 intermolecular interactions of H-bonding between flexible core (adipic acid, A) and lateral chloro-substituted azopyridines (Bn). The chains of the terminally alkoxy substituted base (n) were changed between 8 and 16 carbons. Mesomorphic and optical examinations of the prepared complexes were measured via differential scanning calorimetry (DSC) and polarizing optical microscopy (POM). Fourier-transform infrared spectroscopy (FT-IR) was used to confirm the Fermi bands of the H- bonding interactions. Induced nematogenic mesophases that cover the whole lengths of alkoxy-chains were detected. The non-linear geometries of the designed supramolecular complexes were also confirmed via Density functional theory (DFT) calculations. It was found that the length of terminal alkoxy chain of the base moiety highly affects the geometrical structure of the investigated complexes. Moreover, it increases the thermodynamic energy and influences the geometrical parameters. The electrical properties of each of the acid component (A), the base (B16) and their 1:2 complex (A/2B16) were evaluated using the Keithley measurement-source unit. The optical properties studies showed that the influences in the optical absorption and the reduction of the energy gap of the complex compared to its individual components made the resulted supramolecular H-bonded complex soft material suitable for solar energy investigations.

scholarly journals Nonlinear optical investigation of (E)-1-(4-flourobenzylidene)urea using theoretical calculations

2017 ◽  
Vol 6 (1) ◽  
pp. 26
Author(s):  
Tracy J ◽  
Dhandapani A ◽  
Bharanidharan Bharani
Keyword(s):  
Energy Gap ◽  
Theoretical Calculations ◽  
Nbo Analysis ◽  
Geometrical Parameters ◽  
Optical Investigation ◽  
First Order ◽  
Homo And Lumo ◽  
Ft Ir ◽  
Homo And Lumo Energy ◽  
Ft Raman

The FT-IR and FT-Raman spectra of (E)-1-(4-flourobenzylidene)urea (4FBU) was recorded and analyzed. The optimized geometrical parameters were calculated. The complete vibrationally assignments were performed based on PED analysis with the help of SQM method. NBO analysis was carried out to explore the various conjucative/hyperconjucative interactions within the molecule and their second-order stabilization energy. The HOMO and LUMO energy gap was studied. All theoretical calculations were performed based on B3LYP/6-31G (d,p) level of theory. The first order hyperpolarizability (β0) and related properties (β, α0, Δα) of 4FBU were calculated. Besides, FMOs, MEP, Mulliken atomic charges and various thermodynamic parameters such as entropy, heat capacity and enthalpy were also calculated.

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