ABSTRACT
@#A new synthetic process of pentazocine has been developed. Starting from 3, 4-dimethylpyridin and benzyl chloride, via quaternarization, Grignard reaction addition/reduction/salt, cyclization, hydrogenation, alkylation and recrystallization, pentazocine were obtained in a total yield of 8. 4%(with a molar mass of 3, 4-dimethylpyridin), with purity greater than 99. 97%. The improved synthetic route is suitable for industrial production.
ABSTRACT
In order to develop potent antidiabetic agents that have inhibitory effect to α-glucosidase, twelve β-acetamido ketone derivatives such as N-{[(substituted-4-oxo-thiochroman-3-yl)phenyl]-methyl}acetamide are designed and synthesized through one-pot Dakin-West reaction. Their chemical structures are confirmed by 1H NMR, 13C NMR, IR and HR-MS. In vitro α-glucosidase inhibition assays of compounds 4a-4l were carried out using glucose oxidase method. The result indicated that most of them possess inhibitory activity in vitro. Compound 4k showed the most potent inhibitory activity with 87.3% inhibition of α-glucosidase at the concentration of 5.39 mmol·L-1. The structure-activity relationship of these β-acetamido ketone derivatives was discussed preliminarily. Moreover, the molecular docking method was used to study the interaction mode of compound 4k and α-glucosidase. Our results will be helpful for designing of α-glucosidase inhibitors in the future.
ABSTRACT
Background A simple, rapid, low-cost and environmentally friendly method was developed to determine dopamine (DA) in the presence of ascorbic (AA) and uric acid (UA) based on a novel technique to prepare a graphene-chitosan (GR-CS) nanocomposite and modify it on the surface of carbon paste electrode (CPE). For our design, CS acts as a media to disperse and stabilize GR, and then GR plays a key role to selective and sensitive determination of DA. Results Under physiological conditions, the linear range for dopamine was determined from 1 × 10- 4 to 2 × 10- 7 mol/L with a good correlation coefficient of 0.9961 in the presence of 1000-fold interference of AA and UA. The detection limit was estimated to be 9.82 × 10- 8 mol/L (S/N = 3). In order to study the stability and reproducibility, GR/CS/CPE underwent successive measurements in 10 times and then tested once a d for 30 d. The result exhibited 98.25% and 91.62% activities compared with the original peak current after 10-time measurements and 30-d storage. Conclusion The GR/CS/CPE has wide linear concentration range, low detection limit, and good reproducibility and stability, which suggests that our investigations provide a promising alternative for clinic DA determination.
Subject(s)
Carbon/chemistry , Dopamine/analysis , Chitosan/chemistry , Graphite/chemistry , Electrodes , Nanocomposites/chemistry , Electrochemical Techniques , Limit of Detection , Chemistry Techniques, Synthetic , Hydrogen-Ion ConcentrationABSTRACT
Preparación simple de nuevas N-(6-metil-2-nitrofenil-1,2,3,4-tetrahidroquinolin-4-il) pirrolidin-2-onas y su análisis espectroscópico. Objetivos. Preparar nuevas moléculas N-(1,2,3,4-tetrahidroquinolin-4-il) 2-oxopirrolidínicas y caracterizarlas por métodos espectroscópicos. Materiales y métodos. Todos los reactivos usados son de Aldrich, grado comercial. La pureza de los productos y la composición de las mezclas de reacción fueron monitoreadas por cromatografía en capa fina sobre cromatoplacas de Silufol UV254 (0.25 mm). El aislamiento y purificación se realizó usando cromatografía en columna (SiO2), usando acetato de etilo. Resultados. La preparación de las nuevas N-(tetrahidroquinolin-4-il) pirrolidin-2-onas 4-nitrofenil (ó 2-nitrofenil) sustituidas en C-2 del anillo tetrahidroquinolínico, se realizóvía síntesis one-pot basada en la reacción de cicloadición imino Diels-Alder catalizada por BiCl3 entre toluidina, N-vinilpirrolidin-2-ona y 4-nitrobenzaldehído (3-nitrobenzaldehído). La estructura de los derivados pirrolidónicos fue confirmada por 1H RMN y 13C RMN, además de experimentos 2D RMN y difracción de rayos X de monocristal. Conclusiones. Una ruta eficiente, económica y rápida (reacción imino Diels-Alder multi-componente) fue empleada para la construcción de nuevas moléculas N-(tetrahidroquinolin-4-il) 2-oxopirrolidínicas, esqueleto muy atractivo y usado con estereoquímica bien definida...
Objectives. To prepare new N-(1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-one molecules and to characterize them by spectroscopic methods. Materials and methods. All reagents were purchased from Aldrich, commercial grade. The purity of the products and the composition of the reaction mixtures were monitored by thin layer chromatography over Silufol UV254 chromatoplates (0.25 mm). Product isolation and purification were performed by column chromatography (SiO2) using ethyl acetate. Results. Preparation of new N-(2-nitrophenyl-1,2,3,4-tetrahydroquinolin-4-yl) pyrrolidin-2-ones has been achieved via the one-pot synthesis, based on a BiCl3-catalyzedimino Diels-Alder cycloaddition reaction of toluidine, N-vinylpyrrolidin-2-one and 4-nitro- or 3-nitrobenzaldehydes. The structure of the pyrrolidine derivatives was confirmed by 1H nmr and 13C nmr studies, in addition to inverse-detected 2D NMR experiments and monocrystal X-ray diffraction. Conclusions. An efficient, economic, and fast synthetic route (multi-component imino Diels-Alder reaction) was employed in the construction of several new tetrahydroquinoline derivatives, useful and attractive rigid skeleton with well-defined stereochemistry...
Preparação simples de novas N-(6-metil-2-nitrofenil-1,2,3,4-tetrahydroquinoline-4-il) pirrolidin-2-onas e sua análise espectroscópica. Objetivos. Preparar novas moléculas N-(1,2,3,4-tetrahydroquinoline-4-il) 2-oxopirrolidínicas e sua caracterização por espectroscopia. Materiais e métodos. Todos os reagentes utilizados são de Aldrich, de grau comercial. A pureza dos produtos e a composição das misturas de reação foram monitoradas por cromatografia em camada fina sobre cromatoplacas de Silufol UV254 (0,25 mm). O isolamento e purificação foi realizado utilizando cromatografia em coluna (SiO2), utilizando acetato de etila. Resultados. Preparação de novas N-(tetrahydroquinoline-4-il) pirrolidin-2-onas 4-nitrofenil (ou 2-nitrofenil) substituídas em C-2 do anel tetrahydroquinoline foi realizada através da síntese one pot baseada na reação de cicloadição imino Diels-Alder catalisada por BiCl3 entre toluidina, N-vinilpirrolidin-2-ona e 4 nitrobenzaldehyde (3 nitrobenzaldehyde). A estrutura dos derivados pirrolidónicos foi confirmada por 1H RMN y 13C RMN, experimentos 2D RMN, assim como difração de raios X e monocristais. Conclusões. Uma rota eficiente, econômica e rápida (reação imino Diels-Alder multi-componente) foi utilizada para a construção de novas moléculas N-(tetrahydroquinoline-4-il) 2-oxopirrolidínicas esqueleto muito atraente e usado com estereoquímica bem definida...