- Synthetic method for preparing 5-aminobenzimidazolone
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The invention discloses a synthesis method for preparing 5-aminobenzimidazolone (TM), which comprises the following steps: firstly, carrying out diazotization reaction on aniline to prepare aniline diazonium salt; secondly, coupling the aniline diazonium salt with o-phenylenediamine to generate an azo compound, and carrying out a reaction on the azo compound and urea under the catalysis of concentrated sulfuric acid to generate an azobenzimidazolone compound, and subjecting the azobenzimidazolone compound to a hydrogenation reduction reaction to obtain the target compound 5-aminobenzimidazolone. The method disclosed by the invention is simple in process, high in selectivity and high in product yield, all used reactants are utilized, and the method has very high atom economy. The use of a nitration reagent concentrated nitric acid is avoided, the wastewater and the generation of salt in the wastewater are greatly reduced, and the method is a green production process. In addition, the hydrocracking reduction operation is simple, no other iron mud such as iron powder reduction is generated, no waste residue is basically generated, the quality of a finished product is obviously improved, filter-pressing rinsing water can be repeatedly used for more than multiple times, the cost is reduced, and the environmental pollution is reduced.
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Paragraph 0023; 0031; 0037-0042; 0048-0052
(2021/07/17)
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- NOVEL HYDRAZONE DERIVATIVE WITH ARYL OR HETEROARYL GROUP SUBSTITUTED AT TERMINAL AMINE GROUP THEREOF AND USE THEREOF
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The present invention relates to novel hydrazone derivatives in which a terminal amine group is substituted with an aryl group or a heteroaryl group, and uses thereof.
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Paragraph 0362-0363; 0373
(2021/11/04)
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- Chemoselective Hydrogenation of Nitroaromatics at the Nanoscale Iron(III)–OH–Platinum Interface
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Catalytic hydrogenation of nitroaromatics is an environment-benign strategy to produce industrially important aniline intermediates. Herein, we report that Fe(OH)x deposition on Pt nanocrystals to give Fe(OH)x/Pt, enables the selective hydrogenation of nitro groups into amino groups without hydrogenating other functional groups on the aromatic ring. The unique catalytic behavior is identified to be associated with the FeIII-OH-Pt interfaces. While H2 activation occurs on exposed Pt atoms to ensure the high activity, the high selectivity towards the production of substituted aniline originates from the FeIII-OH-Pt interfaces. In situ IR, X-ray photoelectron spectroscopy (XPS), and isotope effect studies reveal that the Fe3+/Fe2+ redox couple facilitates the hydrodeoxygenation of the -NO2 group during hydrogenation catalysis. Benefitting from FeIII-OH-Pt interfaces, the Fe(OH)x/Pt catalysts exhibit high catalytic performance towards a broad range of substituted nitroarenes.
- Fu, Gang,Li, Laiyang,Ming, Jiang,Qin, Ruixuan,Ren, Juan,Wang, Yongke,Wang, Yu,Zhang, Wuyong,Zheng, Nanfeng,Zhou, Wenting
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supporting information
p. 12736 - 12740
(2020/06/01)
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- Novel hydrazone derivatives comprising aryl or heteroaryl group substituted at terminal amine and use thereof
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The present invention relates to novel hydrazone derivatives with an aryl or heteroaryl group substituted at a terminal amine group thereof and a use thereof.
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Paragraph 1702; 1708; 1709; 1754; 1756-1758
(2020/08/28)
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- Oxidative Cyclization-Induced Activation of a Phosphoinositide 3-Kinase Inhibitor for Enhanced Selectivity of Cancer Chemotherapeutics
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In this work, we designed a prodrug that reacts with cellular oxidative equivalents leading to ether cleavage and cyclization to release an active phosphatidylinositol 3-kinase (PI3K) inhibitor. We show that the compound reduces affinity for PI3KA relative to the PI3K inhibitor, is slow to intercellularly oxidize, and is resistant to liver microsomes. We observed modest activity in untreated acute myeloid leukemia cells and 14-fold selectivity relative to non-cancerous cells. The cellular activity of the compound can be modulated by the addition of antioxidants or oxidants, indicating the compound activity is sensitive to cellular reactive oxygen species (ROS) state. Co-treatment with cytosine arabinoside or doxorubicin was used to activate the compound inside cells. We observed strong synergistic activity specifically in acute myeloid leukemia (AML) cancer cells with an increase in selective anticancer activity of up to 90-fold. Thus, these new self-cyclizing compounds can be used to increase the selectivity of anticancer agents.
- Zhu, Haizhou,Mishra, Rosalin,Yuan, Long,Abdul Salam, Safnas F.,Liu, Jing,Gray, George,Sterling, Alyssa D.,Wunderlich, Mark,Landero-Figueroa, Julio,Garrett, Joan T.,Merino, Edward J.
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p. 1933 - 1939
(2019/11/19)
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- Development of alkyl glycerone phosphate synthase inhibitors: Structure-activity relationship and effects on ether lipids and epithelial-mesenchymal transition in cancer cells
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In aggressive tumors, alkylglyceronephosphate synthase (AGPS) controls cellular ether phospholipid utilization and metabolism to promote cancer cell proliferation and motility. SAR studies on the first-in-class AGPS inhibitor 1, discovered by our group, led to the 2,6-difluoro analog 2i which showed higher binding affinity than 1 in vitro. In 231MFP cancer cells, 2i reduced ether lipids levels and cell migration rate. When tested in PC-3 and MDA-MB-231 cancer cells, 2i specifically impaired epithelial to mesenchymal transition (EMT) by modulating E-cadherin, Snail and MMP2 expression levels. Moreover, the combination of siRNAs against AGPS and 2i provided no additive effect, confirming that the modulation of 2i on EMT specifically relies on AGPS inhibition. Finally, this compound also affected cancer cell proliferation especially in MDA-MB-231 cells expressing higher AGPS level, whereas it provided negligible effects on MeT5A, a non-tumorigenic cell line, thus showing cancer specificity.
- Stazi, Giulia,Battistelli, Cecilia,Piano, Valentina,Mazzone, Roberta,Marrocco, Biagina,Marchese, Sara,Louie, Sharon M.,Zwergel, Clemens,Antonini, Lorenzo,Patsilinakos, Alexandros,Ragno, Rino,Viviano, Monica,Sbardella, Gianluca,Ciogli, Alessia,Fabrizi, Giancarlo,Cirilli, Roberto,Strippoli, Raffaele,Marchetti, Alessandra,Tripodi, Marco,Nomura, Daniel K.,Mattevi, Andrea,Mai, Antonello,Valente, Sergio
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supporting information
p. 722 - 735
(2019/01/04)
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- A one-pot synthesis of 5 - acetyl aminobenzimidazole ketone
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The invention discloses a method for one-pot synthesis of 5-acetylacetamido-benzimidazolone, which comprises the following steps: adding 5-nitrobenzimidazolone, a nickel or palladium carbon catalyst, alcoholic solution and activated carbon into a high-pressure reaction kettle, then introducing hydrogen, filtering out the catalyst and the activated carbon after the completion of reaction, adding diketene dropwise, filtering out after the completion of reaction and drying to obtain the 5-acetylacetamido-benzimidazolone. The invention has the following advantages that the alcoholic solution is used as a solvent during hydrogenation reduction, and the solvent can be recycled, so that the zero discharge of waste liquid is realized; the total yield is more than 76 percent, and the product purity is more than 99.2 percent; the catalyst and the activated carbon can be recycled, so that not only is the pollution reduced, but also the production cost is reduced; no phosphoric acid is used during acylation, so that the difficult problem of difficulty in the treatment of phosphorus wastewater is solved, and meanwhile, the indiscriminate application of mother liquor is realized, so that the purpose of zero discharge is reached; on the premise of not increasing the reaction equipment, the yield is increased by one time.
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Paragraph 0024
(2017/08/25)
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- 2, 4 -DIAMINOPYRIMIDINE DERIVATIVES AS PROTEIN KINASE INHIBITORS
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The present invention relates to novel pyrimide derivatives of formula (I): that are useful as kinase inhibitors. More particularly, the present invention relates to novel pyrimidine compounds, methods for their preparation, pharmaceutical compositions containing these compounds and uses of these compounds in the treatment of proliferative disorders.
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- DIAMINOPYRIMIDINE DERIVATIVES AND PROCESSES FOR THE PREPARATION THEREOF
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The present invention provides a diaminopyrimidine derivative or its pharmaceutically acceptable salt, a process for the preparation thereof, a pharmaceutical composition comprising the same, and a use thereof. The diaminopyrimidine derivative or its pharmaceutically acceptable salt functions as a 5-HT4 receptor agonist, and therefore can be usefully applied for preventing or treating dysfunction in gastrointestinal motility, one of the gastrointestinal diseases, such as gastroesophageal reflux disease (GERD), constipation, irritable bowel syndrome (IBS), dyspepsia, post-operative ileus, delayed gastric emptying, gastroparesis, intestinal pseudo-obstruction, drug-induced delayed transit, or diabetic gastric atony.
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Page/Page column 23
(2012/09/11)
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- ISOINDOLINE COMPOUNDS FOR THE TREATMENT OF SPINAL MUSCULAR ATROPHY AND OTHER USES
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Disclosed is a compound of Formula (I) in which W and R1-R6 are defined herein. Also disclosed is a method of treating spinal muscular atrophy, as well as methods of using such compounds to increase SMN expression, increase EAAT2 expression, or increase the expression of a nucleic acid that encodes a translational stop codon introduced directly or indirectly by mutation or frameshift.
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Page/Page column 78-79
(2009/05/29)
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