- Method for preparing 6,7-dihydro-5H-pyrrolo-pyridine hydrochloride
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The invention discloses a preparation method for preparing 6,7-dihydro-5H-pyrrolo-pyridine hydrochloride. The method is characterized in that a target product 6,7-dihydro-5H-pyrrolo-pyridine hydrochloride is obtained through lactamization, reduction and salifying by taking furo[3,4-b]pyridine-5,7-dione as an original raw material. The compound is an important medical intermediate.
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Paragraph 0020-0022
(2017/10/31)
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- (S, S) - 2,8-diazabicyclo [4.3.0] nonane preparation method
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The invention relates to a novel preparation method of (S,S)-2,8-diazabicyclo[4.3.0]. The method comprises the steps that: 2,3-pyridine dicarboxylic acid derivative and amide are subjected to condensation, such that 2,3-pyridine dicarboximide is formed; 2,3-pyridine dicarboximide is subjected to protection and hydrogenation reduction, such that 8-substituted-7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane is produced; the product is reduced in a borohydride reduction system, such that 8-substituted-2,8-diazabicyclo[4.3.0]nonane is obtained; the product is subjected to optical-active organic acid resolution, such that 8-site protection group is removed, and the final product is obtained. Or, 2,3-pyridine dicarboximide is directly subjected to hydrogenation reduction, such that 7,9-dioxo-2,8-diazabicyclo[4.3.0]nonane is produced; the product is directly reduced in a borohydride reduction system, such that 2,8-diazabicyclo[4.3.0]nonane is produced; the 2,8-diazabicyclo[4.3.0]nonane is subjected to optical-active organic acid resolution, such that the final product is directly obtained. The method provided by the invention is advantaged in simple reaction route. The raw materials are cheap and easy to obtain. The reaction conditions are mild and easy to control. The method is suitable for industrialized productions.
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Paragraph 0077; 0078
(2017/02/09)
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- New artificial fluoro-cofactor of hydride transfer with novel fluorescence assay for redox biocatalysis
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A new artificial fluoro-cofactor was developed for the replacement of natural cofactors NAD(P), exhibiting a high hydride transfer ability. More importantly, we established a new and fast screening method for the evaluation of the properties of artificial cofactors based on the fluorescence assay and visible color change.
- Zhang, Lei,Yuan, Jun,Xu, Yufang,Zhang, Y.-H. Percival,Qian, Xuhong
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supporting information
p. 6471 - 6474
(2016/06/06)
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- Synthetic method of 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridyl-5,7-dione
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The invention particularly relates to a synthetic method of 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridyl-5,7-dione. The synthetic method is characterized in that 2,3-pyridinedicarboxylic acid and urea are subjected to melt reaction to produce amide, then amide reacts with methylbenzylamine to produce a crude product 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridyl-5,7-dione which is subjected to chiral resolution to obtain the target product 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridyl-5,7-dione. The synthetic method has the advantages that the reaction steps are simple and short, the reaction is quick, no by-product is produced, environmental pollution is reduced, the reaction yield is high, the separation efficiency of a chiral chromatographic column is relatively high, and the product purity is improved.
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Paragraph 0013; 0014; 0015
(2017/07/21)
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- Method for preparing 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridine-5,7-dione
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The invention more specifically relates to a method for preparing 6-(1-phenyl-ethyl)-pyrrolo[3,4-b]pyridine-5,7-dione. The preparation method comprises the following steps: 5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione is generated from 2,3-dipicolinic acid and urea, ethylbenzene and hydrogen halide are reacted in order to generate (1-haloethyl)benzene, (1-haloethyl)benzene and 2,3-dipicolinic acid are generated into a crude product, and finally a target compound is obtained by chiral separation. The method is advantageous in that the synthesis technology has the advantages of mild reaction condition, short reaction time, high yield without generation of harmful refuses, simple post-treatment, recycling of 1,2-dichloroethane solvent which is separated from the reaction process, and easy industrialization.
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Paragraph 0016
(2017/05/26)
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- Pyridine salt / 1,4-dihydropyridine derivative and preparation method thereof
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The present invention discloses a pyridine salt / 1,4-dihydropyridine derivative (NAD / NADH analog) with novel structure. The NAD / NADH analog can substitute natural NAD / NADH to be applied to a biochemical system for redox reactions, and can also be used as an electron carrier for the energy transfer of an enzymatic fuel cell. Further, the NAD / NADH analogs provided by the invention are easy to prepare, isolate and purify, and have a high yield.
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Paragraph 0149; 0150; 0151
(2016/10/09)
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- Zinc-catalyzed selective reduction of cyclic imides with hydrosilanes: Synthesis of ω-hydroxylactams
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Cyclic imides were selectively reduced to the corresponding ω-hydroxylactams in high yields with (EtO)3SiH (triethoxysilane) or PMHS (polymethylhydrosiloxane) under catalysis of zinc diacetate dehydrate [Zn(OAc)2 2H2O] (10%) and tetramethylethylenediamine (TMEDA) (10%). This catalytic protocol showed good functional group tolerance as well as excellent regioselectivity for unsymmetrical imides bearing coordinating groups adjacent to the carbonyl.
- Ding, Guangni,Lu, Bin,Li, Yuyuan,Wan, Jun,Zhang, Zhaoguo,Xie, Xiaomin
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supporting information
p. 1013 - 1021
(2015/03/30)
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- Identification of a sirtuin 3 inhibitor that displays selectivity over sirtuin 1 and 2
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As part of an effort to identify novel selective modulators of sirtuins, we synthesized and tested several isosteres and constrained analogues of nicotinamide. Biological data suggest that compound 2 is selective for Sirt3 over Sirt1 and Sirt2.
- Galli, Ubaldina,Mesenzani, Ornella,Coppo, Camilla,Sorba, Giovanni,Canonico, Pier Luigi,Tron, Gian Cesare,Genazzani, Armando A.
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p. 58 - 66,9
(2020/07/31)
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- New efficient access to fused (Het)Aryltetrahydroindolizinones via N-acyl iminium intermediates
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In this paper, we described the preparation of fused (Het)Aryltetrahydroindolizinones via N-acyl iminium intermediates. Two different routes were also explored to achieve the synthesis. The first one consists in the intramolecular reaction of β-hydroxylactams whereas the second route one is an intermolecular condensation between a 2-formylester or a β-alkoxylactone and an appropriate primary amine. We also developed two heterocyclic strategies to obtain the adequate unavailable starting materials in pyridine, pyrazine, quinoline, and quinaxoline series and then perform all inter or intramolecular reactions. Scope and limitations are given.
- Chiurato, Matteo,Boulahjar, Rajaa,Routier, Sylvain,Troin, Yves,Guillaumet, Gérald
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scheme or table
p. 4647 - 4653
(2010/07/05)
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- Aza-and polyaza-naphthalenly ketones useful as hiv integrase inhibitors
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Certain aza- and polyaza-naphthalenyl ketones including certain quinolinyl and naphthyridinyl ketones are described as inhibitors of HIV integrase and inhibitors of HIV replication. These compounds are useful in the prevention or treatment of infection by HIV and the treatment or the delay in the onset of AIDS, as compounds or pharmaceutically acceptable salts, or as ingredients in pharmaceutical compositions, optionally in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating or delaying the onset of AIDS and methods of preventing or treating infection by HIV are also described.
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Page/Page column 60
(2010/02/10)
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- Improved synthesis of N-substituted 2,3-pyridine-dicarboximides with microwave irradiation
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The microwave-induced synthesis of N-substituted 2,3- pyridinedicarboximides (1) by means of two different approaches is presented. One involves direct N-alkylation of quinolinimide (2) (Method A) and the other, dehydrative condensation of quinolinic anhydride (4) and amines (Method B). Reactions resulted highly accelerated, with improved yields in relation to those obtained by conventional heating. The scope and limitations of each method and its variants are discussed.
- Blanco, Maria M.,Levin, Gustavo J.,Schapira, Celia B.,Perillo, Isabel A.
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p. 1881 - 1890
(2007/10/03)
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- Synthesis and SAR of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one as NMDA/glycine site antagonists
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A series of 5-, 6-, 7- and 8-aza analogues of 3-aryl-4-hydroxyquinolin-2(1H)-one was synthesized and assayed as NMDA/glycine receptor antagonists. The in vitro potency of these antagonists was determined by displacement of the glycine site radioligand [3H]5,7-dicholorokynurenic acid ([3H]DCKA) in rat brain cortical membranes. Selected compounds were also tested for functional antagonism using electrophysiological assays in Xenopus oocytes expressing cloned NMDA receptor (NR) 1A/2C subunits. Among the 5-, 6-, 7-, and 8-aza-3-aryl-4-hydroxyquinoline-2(1H)-ones investigated, 5-aza-7-chloro-4-hydroxy-3-(3-phenoxyphenyl)quinolin-2-(1H)-one (13i) is the most potent antagonist, having an IC50 value of 110 nM in [3H]DCKA binding and a Kb of 11 nM in the electrophysiology assay. Compound 13i is also an active anticonvulsant when administered systemically in the mouse maximum electroshock-induced seizure test (ED50 = 2.3 mg/kg, IP).
- Zhou, Zhang-Lin,Navratil, James M.,Cai, Sui Xiong,Whittemore, Edward R.,Espitia, Stephen A.,Hawkinson, Jon E.,Tran, Minhtam,Woodward, Richard M.,Weber, Eckard,Keana, John F.W.
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p. 2061 - 2071
(2007/10/03)
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- Improved synthesis of N-substituted quinolinimides using microwave irradiation
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The synthesis of several quinolinimidoacetic acid derivatives (I) by two different routes, starting from quinolinic anhydride or quinolinimide, is described. In all cases better yields and decreased reaction times were achieved employing microwave irradia
- Blanco,Perillo,Schapira
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p. 481 - 482
(2007/10/03)
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- Evaluation and Synthesis of Aminohydroxyisoxazoles and Pyrazoles as Potential Glycine Agonists
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Except for structurally similar small amino acids, such as alanine, β-alanine, and serine, compounds acting as glycine-receptor agonists are an unknown class of pharmacological agents.To investigate the potential of small, substituted heterocycles to act as glycine agonists, we have evaluated the similarities between glycine and a series of hydroxy- and amino-substituted pyrazoles and isoxazoles through complementary molecular modeling techniques.Using a "scorecard approach" to determine the overall similarity of projected agonist structures to glycine, we prioritized synthesis and subsequently prepared several novel derivatives.The biological activity of these compounds was compared to that of glycine by using a strychnine-mediated glycine receptor binding assay.Despite the close similarity in the calculated parameters when compared to glycine, no significant receptor-binding activity was observed for the targeted analogues.These results illustrate the structurally exacting nature of the glycine receptor.
- Drummond, J.,Johnson, G.,Nickell, D. G.,Ortwine, D. F.,Bruns, R. F.,Welbaum, B.
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p. 2116 - 2128
(2007/10/02)
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- PREPARATION AND STRUCTURAL ASSIGNMENTS OF SOME ISOMERIC 2,3-DISUBSTITUTED PYRIDINES
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The preparation of several isomeric 2,3-disubstituted pyridine compounds are described and their spectroscopical data given.IR and NMR spectra of quinolinimide, reported by Distefano et al., are contradicted.The electron impact mass spectra are found to be useful in the differentiation between positional isomers.
- Spiessens, Luc I. M.,Anteunis, Marc J. O.
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p. 205 - 232
(2007/10/02)
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- Azaisatoic anhydrides
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A method for producing heterocyclic acid anhydrides and pyrimidinediones from the corresponding acids, dicarboxamides, 2,3-and 3,4-pyridinedicarboxamides, and N-monosubstituted 2,3-and 3,4-pyridinedicarboxamides, in which the aforesaid compounds are reacted with lead tetra-acetate in the presence of a suitable anhydrous inert solvent.
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