- Mechanochemical catalytic transfer hydrogenation of aromatic nitro derivatives
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Mechanochemical ball milling catalytic transfer hydrogenation (CTH) of aromatic nitro compounds using readily available and cheap ammonium formate as the hydrogen source is demonstrated as a simple, facile and clean approach for the synthesis of substituted anilines and selected pharmaceutically relevant compounds. The scope of mechanochemical CTH is broad, as the reduction conditions tolerate various functionalities, for example nitro, amino, hydroxy, carbonyl, amide, urea, amino acid and heterocyclic. The presented methodology was also successfully integrated with other types of chemical reactions previously carried out mechanochemically, such as amide bond formation by coupling amines with acyl chlorides or anhydrides and click-type coupling reactions between amines and iso(thio)cyanates. In this way, we showed that active pharmaceutical ingredients Procainamide and Paracetamol could be synthesized from the respective nitro-precursors on milligram and gram scale in excellent isolated yields.
- Portada, Tomislav,Margeti?, Davor,?trukil, Vjekoslav
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supporting information
(2018/12/11)
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- Boron trifluoride-methanol complex. Mild and powerful reagent for deprotection of acetylated amines. Scope and selectivity
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A boron trifluoride-methanol complex demonstrated remarkable deprotection selectivity against commonly used amino-protecting groups in the deacetylation of acetanilides and high sensitivity to the steric hindrance of substrates. The scope and limitations of the reaction were explored.
- Miltsov, Sergey,Karavan, Vladimir,Misharev, Alexandr,Alonso-Chamarro, Julian,Puyol, Mar
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supporting information
p. 641 - 644
(2016/01/26)
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- Process for the preparation of an anticonvulsant compound
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The invention provides a novel method for the preparation of intermediates useful in a process designed to obtain known 1,2,4-triaminobenzene compounds, and in particular a specific compound thereof having known anticonvulsant activity. Unlike known methods, the novel method does not require advance protection of the amino groups present on the substrate.
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Paragraph 0031
(2014/05/24)
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- PROCESS FOR THE PREPARATION OF AN ANTICONVULSANT COMPOUND
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The invention provides a novel method for the preparation of intermediates useful in a process designed to obtain known 1,2,4-triaminobenzene compounds, and in particular a specific compound thereof having known anticonvulsant activity. Unlike known methods, the novel method does not require advance protection of the amino groups present on the substrate.
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Paragraph 0036-0037
(2014/06/24)
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- Synthesis and structure-activity relationships of (aryloxy)quinazoline ureas as novel, potent, and selective vascular endothelial growth factor receptor-2 inhibitors
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In our continuing search for medicinal agents to treat proliferative diseases, quinazoline derivatives were synthesized and evaluated pharmacologically as epithelial growth factor receptor and vascular endothelial growth factor receptor 2 (VEGFR-2) tyrosine kinase inhibitors. A quantitative structure-activity relationship analysis was conducted to rationalize the structure-activity relationship and to predict how similar the inhibitor-binding profiles of two protein kinases are likely to be on the basis of the docking of lead coumpounds into the ATP-binding site. This model was used to direct the synthesis of new compounds. A series of N-(aromatic)-N′-{4-[(6,7- dimethoxyquinazolin-4-yl)oxy]phenyl}urea were identified as potent and selective inhibitors of the tyrosine kinase activity of VEGFR-2 (fetal liver kinase 1, kinase insert domain-containing receptor). An efficient route was developed that enabled the synthesis of a wide variety of analogues with substitution on several positions of the template. Substitution of diarylurea, competitive with ATP, afforded several analogues with low nanomolar inhibition of enzymatic activity of VEGFR-2. In this paper, we describe the synthesis, structure-activity relationships, and pharmacological characterization of the series.
- Garofalo, Antonio,Farce, Amaury,Ravez, Séverine,Lemoine, Amélie,Six, Perrine,Chavatte, Philippe,Goossens, Laurence,Depreux, Patrick
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scheme or table
p. 1189 - 1204
(2012/03/27)
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- Novel and efficient one-pot synthesis of (aminophenyl)carbamic acid esters
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A novel and efficient protocol is developed for the synthesis of various (aminophenyl) carbamic acid esters from the reduction and condensation of nitrophenyl isocyanate derivatives. The reaction takes place in various hydroxy derivatives such as alcohols or phenols under a hydrogen atmosphere using Raney nickel as catalyst. Products are obtained by a convenient one-pot synthesis with excellent yields and short reaction times.
- Garofalo, Antonio,Goossens, Laurence,Six, Perrine,Lebegue, Nicolas,Depreux, Patrick
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body text
p. 2007 - 2016
(2011/06/24)
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- 1,2,4-TRIAMINOBENZENE DERIVATIVES USEFUL FOR TREATING DISORDERS OF THE CENTRAL NERVOUS SYSTEM
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The present invention concerns 1,2,4-triaminobenzene derivatives of the general formula I or pharmaceutically acceptable salts thereof and the use thereof.
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- SUBSTITUTED P-DIAMINOBENZENE DERIVATIVES
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The present invention relates to aniline derivatives of the general formula I or pharmaceutically acceptable salts thereof and their use.
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Page/Page column 102
(2010/02/08)
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- Synthesis of alkyl N-(C-nitrosoaryl)carbamates and some reactions thereof
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Reactions of alkyl N-phenylcarbamates, m-di(methoxycarboxyamido)benzene, and methyl N-(o-tolyl)carbamate with nitrosylsulfuric acid in glacial acetic acid afford N-(C-nitrosoaryl)carbamates; under these conditions tert-bulyl N-phenylcarbamate suffers decarboxylation, methyl N-(p-tolyl)-, methyl N-(p-methoxyphenyl)carbamates, o-and p-di(methoxycarboxyamido)benzenes are nitrated, and isomeric methyl N-nitrophenylcarbamates and methyl N-(p-bromophenyl)carbamate do not react. The reduction of N-(C-nitrosoaryl)carbamates with dithionite afforded the corresponding aminocarbamates; the oxidation with nitric acid yielded carbamate nitro derivatives; the condensation with aniline and benzylpyridinium chloride resulted in carbamate derivatives of azobenzene and phenylnitron.
- Velikorodov
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p. 233 - 239
(2007/10/03)
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- Synthesis of some new 7-chloro-4-substituted quinolines as potential antiparasitic agents. I
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The synthesis of 7-chloro-4-(substituted phenoxyquinolines, 7-chloro-4-(substituted phenylamino)quinolines and 7-chloro-4-(4-substituted phenylthio and sulfonyl)quinolines and 1-(7-chloroquinolin-4-yl)-4-substituted-piperazines has been carried out starting from 4,7-dichloroquinoline. The compounds were tested for their antimalarial activity against Plasmodium berghei in mice, antihookworm activity against Ancylostoma cylanicum in hamsters and anticestode activity against Hymenolepis nana in rats but none of them showed significant activity. When tested against Litomosoides carinii infection in cotton rats, two of the substituted piperazine compounds led to a 100% reduction of microfilariae in blood at an i.p. dose of 30 mg/kg given for 6 days.
- Abuzar,Dubey,Sharma
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