A series of 5-aryl-2-methylthio-5,12-dihydrobenzo[g]pyrimido [4,5-b]quinoline-4,6,11(3H) -trione was synthesized through an environmental friendly multicomponent methodology and characterized with FT-IR (Fourier Transform infrared spectroscopy), 1 H NMR (Nuclear Magnetic Resonance ), 13 C NMR and GC-MS (gas chromatography-mass spectrometry). The 5-(4-methoxyphenyl)-2-methylthio-5,12-dihydrobenzo[g]pyrimido [4,5-b]quinoline-4,6,11(3H)-trione 4c compound was characterized by X-ray single crystal diffraction. The geometry of 4c has been fully optimized using DFT (Density functional theory), B3LYP functional and 6-31G(d,p) basis set, thus establishing the ground state energy and thermodynamic features for the mentioned compound, which are in accordance with the experimental data and the crystal structure. The experimental results reveal a strong preference for the regioselective formation of 4c linear four fused rings over the angular four fused and suggest a possible kinetic control in product formation.
We report the experimental results of unexpected aromatic nucleophilic substitution reaction products on 2-amino-4,6-dichloropyrimidine-5-carbaldehyde. The isolated compounds are products of amination, solvolysis, and condensation processes under mild and environmentally friendly conditions, due to the influence of structural factors of the starting pyrimidine and a high concentration of alkoxide ions. This method allows the building of pyrimidine-based compound precursors of N-heterocyclic systems.
Los parámetros estructurales de 1,3,5-trifenilpirazol se determinaron con DFT/cam-B3LYP con el conjunto de bases 6-311++G(d,p). Los resultados de la estructura molecular optimizada se presentan y comparan con los datos disponibles de rayos X de la molécula o moléculas muy similares. Se proporciona un análisis completo de los espectros observados de las mediciones espectrales de FT-IR, RMN (1H y 13C) y absorción UV-Vis con TD-DFT en la misma función y conjunto de bases. Los descriptores de reactividad global y local han sido determinados. Las propiedades ONL de esta molécula también fueron investigadas. Las distribuciones de cargas del análisis de poblaciones naturales y el mapa de potencial electrostático están correlacionados. Los resultados calculados y los hallazgos experimentales se discuten y se correlacionan
5-Aryl-3-(2-methoxynaphthalen-6-yl)-1-phenylpyrazoline derivatives were synthesized starting from (E)-1-(3-aryl)-(2-methoxynaphthalen-6-yl)-prop-2-en-1-one and phenylhydrazine. The compounds were characterized by 1 H and 13 C nuclear magnetic resonance (NMR), elemental analyses and mass spectrometry. Some compounds showed promising luminescence properties in solution and in solid state; the absorption and emission characteristics were measured and the fluorescence quantum yield of two of the derivatives [4,5-dihydro-3-(2-methoxynaphthalen-6-yl)-5-(3,4,5-trimethoxyphenyl)-1-phenyl-1H-pyrazoline and 5-(4-chlorophenyl)-4,5-dihydro-3-(2-methoxynaphthalen-6-yl)-1-phenyl-1H-pyrazoline] were found to have excellent values compared to rhodamine B standard. Theoretical calculations at time-dependent density functional theory (TD-DFT) level are in agreement with the experimental measurements and are helpful to explain the electronic behavior.
Quantitative structureÀ activity relationship(QSAR) modeled the biological activities of 30 cannabinoids with quantum similarity descriptors(QSD) and Comparative Molecular Field Analysis (CoMFA). The PubChem[https://pubchem.ncbi.nlm.nih.gov/] database provided the geometries, binding affinities(K i ) to the cannabinoid receptors type 1(CB1) and 2(CB2), and the median lethal dose(LD 50 ) to breast cancer cells. An innovative quantum similarity approach combining (self)-similarity indexes calculated with different charge-fitting schemes under the Topo-Geometrical Superposition Algorithm(TGSA) were used to obtain QSARs. The determination coefficient(R 2 ) and leave-oneout cross-validation[Q 2 (LOO)] quantified the quality of multiple linear regression and support vector machine models. This approach was efficient in predicting the activities, giving predictive and robust models for each endpoint [pLD 50 : R 2 = 0.9666 and Q 2 (LOO) = 0.9312; pK i (CB1): R 2 = 1.0000 and Q 2 (LOO) = 0.9727, and pK i (CB2): R 2 = 0.9996 and Q 2 (LOO) = 0.9460], where p is the negative logarithm. The descriptors based on the electrostatic potential encrypted better electronic information involved in the interaction. Moreover, the similaritybased descriptors generated unbiased models independent of an alignment procedure. The obtained models showed better performance than those reported in the literature. An additional 3D-QSAR CoMFA analysis was applied to 15 cannabinoids, taking THC as a template in a ligand-based approach. From this analysis, the region surrounding the amino group of the SR141716 ligand is the more favorable for the antitumor activity.
En química medicinal, se dirigen continuamente extensos esfuerzos en investigación al descubrimiento de nuevos heterociclos con efectos farmacológicos apropiados. Específicamente, el papel de los derivados del pirazol en la química médica es vital debido a su amplia gama de actividades biológicas. Por esta notable observación, se desarrolla esta revisión con enfoque sobre los avances de procedimientos sintéticos eco-amigables en términos de rendimiento, tiempo de reacción corto y condiciones limpias en la obtención de 2-pirazolinas, a partir de un análisis bibliográfico de investigación que toma como referencia los años 2019 a 2021 con respecto a la obtención de estos sistemas en condiciones simplificadas y energéticamente sustentables.
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