24318-00-1Relevant academic research and scientific papers
Synthesis of 14C-labeled 4-hydroxyindole as an intermediate for the preparation of (S)-2-14-12-13-(indol-2-[14C]-4-yloxy)-2-hydroxypropylaminol -2-methylpropyl]- phenoxylpyridine-5-carboxamide (LY368842-[indole-14C]) glyco
Czeskis, Boris A.,Clodfelter, Dean K.,Wheeler, William J.
, p. 1143 - 1152 (2002)
Synthesis of 4-hydroxyindole labeled with 14C at the 2-position was accomplished based on the vicarious nucleophilic substitution reaction of benzyl-protected 3-nitrophenol with p-chlorophenoxyacetonitrile-[1-14C]. This was followed
Preparation method of M-aminophenol
-
Paragraph 0023; 0025; 0027; 0029; 0031, (2020/12/14)
The invention discloses a preparation method of m-aminophenol. The preparation method comprises the following steps: 1, using m-dinitrobenzene and benzyl alcohol as raw materials, adding an organic solvent 1, inorganic alkali and a phase transfer catalyst, stirring and heating to 60-150 DEG C, reacting for 3-8 hours, and cooling and concentrating the reaction product to obtain an m-nitrobenzyl ether intermediate product; 2, putting the m-nitrobenzyl ether intermediate product into an organic solvent 2, under the action of a hydrogenation reduction catalyst, hydrogen, hydrazine hydrate or ammonium formate is used as a hydrogen source, a reduction reaction is carried out, after the reaction is completed, the hydrogenation reduction catalyst is filtered and recovered, filtrate is subjected toconcentration, alkali liquor treatment and toluene extraction separation to recover a solvent, a water phase is subjected to acid neutralization to separate out a product, and recrystallization, filtration and vacuum drying are carried out to obtain an m-aminophenol target product. The method is mild in reaction condition and high in yield; high-temperature operation in the production process isavoided; the catalyst and the solvent can be recycled; subsequent treatment environmental protection pressure is low.
A inter-b-aminophenol preparation method
-
Paragraph 0052-0054, (2019/07/01)
The invention belongs to organic synthesis and chemical raw material preparation technical field, and in particular relates to inter-b-aminophenol and intermediate preparation method, inter-b-aminophenol of the preparation method, comprises the steps of: (1) dinitrobenzene substituted benzyl alcohol generated by the reaction with 1 - benzyloxy - 3 - nitrophenyl; (2) 1 - benzyloxy - 3 - nitrobenzene with acetaldehyde in the foaming PH to acid substituted in the reaction solution, or 1 - benzyloxy - 3 - nitrobenzene with acetaldehyde to replace after the recovery of the solvent of the reaction solution dissolved in the dissolving of the re-dissolved solution in organic solvent, by reducing amination and catalytic debenzylation of hydrogenation generating inter-b-aminophenol. 1 - Benzyloxy - 3 - nitrophenyl without separation and purification, directly with the aldehyde and hydrogen reduction amination and debenzylation of hydrogenation reaction. The method is simple, mild condition, equipment strength requirement is low, not produce waste, environment friendly, easily available raw materials, high yield, is suitable for the large-scale generation.
A preparation method of the m-aminophenol
-
Paragraph 0014; 0038-0041, (2019/07/08)
The invention belongs to organic synthesis and chemical raw material preparation technology field, in particular to m-aminophenol of preparation method and its intermediate, m-aminophenol of the preparation method, comprises the steps of: (1) dinitrobenzene substituted with benzyl alcohol produced by the reaction of 1 - benzyloxy - 3 - nitrophenyl; (2) 1 - benzyloxy - 3 - nitrobenzene for filtering of the alkaline inorganic salt the substitution reaction of the liquid catalytic hydrogenation generating m-aminophenol; or, 1 - benzyloxy - 3 - nitrophenyl replace alkaline inorganic salt and filtered out of the reaction solution after the recovery of the solvent is soluble in the organic solvent and then re-dissolved in the solution of the, generated by the catalytic hydrogenation of m-aminophenol. Without intermediate separation and purification processes, direct catalytic hydrogenation "one-pot" process for preparing m-aminophenol; then the re-crystallization or reduced pressure distillation purification of m-aminophenol. The method is simple, mild reaction conditions, equipment strength requirement is low, not generate intermediate waste, environment-friendly, high yield, is suitable for industrial generation.
[Cp?RhCl2]2-catalyzed alkyne hydroamination to 1,2-dihydroquinolines
Kumaran, Elumalai,Leong, Weng Kee
, p. 1779 - 1782 (2015/05/20)
[Cp?RhCl2]2 catalyzes the formation of 1,2-dihydroquinolines from the reaction of two terminal alkynes and an aniline. This reaction is believed to proceed via an alkyne hydroamination followed by an alkyne insertion.
Copper MOF: Scope and limitation in catalytic hydroxylation and nitration of aryl halides
Priyadarshini,Amal Joseph,Kantam, M. Lakshmi,Sreedhar
, p. 6409 - 6414 (2013/07/26)
The potential catalytic application of MOFs like [Cu3(btc) 2] (btc=1,3,5-benzenetricarboxylate), [Cu(bdc)] (bdc=1,4- benzenedicarboxylate), [Cu(pymo)2] (pymo=2-hydroxypyrimidinalote) and [Cu(im)2] (im=imidazolate) was explored in the hydroxylation and nitration of aryl halides. Cu3(btc)2 was found to be superior for both the reactions furnishing good to excellent yields of the respective products. The studies demonstrated that MOFs are not recyclable, attributable to their instability in the highly polar and basic conditions demanded for these reactions. Complete transformation of MOFs to copper oxide nanoparticles occurred in hydroxylation, whereas significant alteration in frameworks was observed for the recovered catalyst in nitration.
Synthesis and biological evaluation of direct thrombin inhibitors bearing 4-(piperidin-1-yl)pyridine at the P1 position with potent anticoagulant activity
De Candia, Modesto,Fiorella, Filomena,Lopopolo, Gianfranco,Carotti, Andrea,Romano, Maria Rosaria,Lograno, Marcello Diego,Martel, Sophie,Carrupt, Pierre-Alain,Belviso, Benny D.,Caliandro, Rocco,Altomare, Cosimo
, p. 8696 - 8711 (2013/12/04)
The design and synthesis of a new class of nonpeptide direct thrombin inhibitors, built on the structure of 1-(pyridin-4-yl)piperidine-4-carboxamide, are described. Starting from a strongly basic 1-amidinopiperidine derivative (6) showing poor thrombin (fIIa) and factor Xa (fXa) inhibition activities, anti-fIIa activity and artificial membrane permeability were considerably improved by optimizing the basic P1 and the X-substituted phenyl P4 binding moieties. Structure-activity relationship studies, usefully complemented with molecular modeling results, led us to identify compound 13b, which showed excellent fIIa inhibition (Ki = 6 nM), weak anti-Xa activity (K i = 5.64 μM), and remarkable selectivity over other serine proteases (e.g., trypsin). Compound 13b showed in vitro anticoagulant activity in the low micromolar range and significant membrane permeability. In mice (ex vivo), 13b demonstrated anticoagulant effects at 2 h after oral dosing (100 mg·kg-1), with a significant 43% prolongation of the activated partial thromboplastin time (aPTT), over controls (P 0.05).
Copper catalyzed ipso-nitration of iodoarenes, bromoarenes and heterocyclic haloarenes under ligand-free conditions
Amal Joseph,Priyadarshini,Lakshmi Kantam,Maheswaran
supporting information; experimental part, p. 1511 - 1513 (2012/03/27)
A catalytic protocol for the conversion of haloarenes into the corresponding nitroarenes is presented using copper salts under ligand-free conditions. The method was effectively utilized for the ipso-nitration of a broad variety of haloarenes that includes iodoarenes, bromoarenes, and heterocyclic haloarenes.
Synthesis of novel 5-substituted isoxazole-3-carboxamide derivatives and cytotoxicity studies on lung cancer cell line
Veeraswamy,Kurumurthy,Santhosh Kumar,Sambasiva Rao,Thelakkat, Kavya,Kotamraju, Srigiridhar,Narsaiah
, p. 1369 - 1375 (2012/11/13)
A series of novel 5-substituted isoxazole-3-carboxamide derivatives 6 have been prepared by coupling of 5-substituted isoxazole-3-carboxylic acids 3 with substituted-3-benzyloxyaniline 5 using DCC/HOBT as coupling agent. The products 6 have been evaluated for cytotoxicity on A549 lung cancer cell line and compounds 6a, 6b, 6e, 6j are found to show moderate proliferative activity and low cytotoxicity.
Fluorinated benzyloxyphenyl piperidine-4-carboxamides with dual function against thrombosis: Inhibitors of factor xa and platelet aggregation
De Candia, Modesto,Liantonio, Francesco,Carotti, Andrea,De Cristofaro, Raimondo,Altomare, Cosimo
experimental part, p. 1018 - 1028 (2009/12/24)
A series of benzyloxy anilides of nipecotic (5, 6) and isonipecotic (7, 8) acids were synthesized and assayed in vitro as inhibitors of ADP-induced platelet aggregation and the blood coagulation enzymes factor Xa (FXa) and thrombin (Flla). An exploration of effects of the amidine group attached at the piperidine nitrogen, position and substitution (F, phenyl) of the benzyloxy group, and addition of fluorine/s on the second (distal) phenyl ring, led us to single out some promising isonipecotamide derivatives 7. Addition of meta-F and para-CF3 on the distal phenyl ring resulted in a 6-to-18-fold enhancement of the FXa potency and in 2-to- 4-fold increase of the antiplatelet potency, the last depending to a large extent upon lipophilicity. Two congeners of N-{[3-(1,1′-biphenyl-4-yl)methoxy]phenyljpiperidine-4-carboxamide (7m and 7p) proved to be potent FXa-selective inhibitors (Ki = 130 and 57 nM, respectively) and antiplatelet agents and were identified as leads for developing new dual function antithrombotic drugs.
