1068-90-2Relevant articles and documents
Organocatalytic Enantioselective Addition of α-Aminoalkyl Radicals to Isoquinolines
Liu, Xiangyuan,Liu, Yang,Chai, Guobi,Qiao, Baokun,Zhao, Xiaowei,Jiang, Zhiyong
, p. 6298 - 6301 (2018)
With a dual organocatalytic system involving a chiral phosphoric acid and a dicyanopyrazine-derived chromophore (DPZ) photosensitizer and under the irradiation with visible light, an enantioselective Minisci-type addition of α-amino acid-derived redox-active esters (RAEs) to isoquinolines has been developed. A variety of prochiral α-aminoalkyl radicals generated from RAEs were successfully introduced on isoquinolines, providing a range of valuable α-isoquinoline-substituted chiral secondary amines in high yields with good to excellent enantioselectivities.
Improved Reagent for Electrophilic Amination of Stabilized Carbanions
Smulik, Jason A.,Vedejs, Edwin
, p. 4187 - 4190 (2003)
(Equation presented) Enolate amination using O-di(p-methoxyphenyl) phosphinylhydroxylamine 2 is reported. Reagent 2 reacts efficiently with stabilized sodium or potassium enolates derived from malonates, phenylacetates, and phenylacetonitriles and is sufficiently soluble for use in solution at -78°C.
Synthesis method of diethyl acetamidomalonate
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Paragraph 0018-0027, (2021/07/17)
The invention discloses a synthesis method of diethyl acetamidomalonate, which comprises the steps of sequentially adding glacial acetic acid and a sodium nitrite solution into diethyl malonate, carrying out heat preservation reaction, standing for layering, and taking an oil layer solution; and sequentially adding glacial acetic acid, potassium borohydride, methanol and acetic anhydride into the oil layer solution, stirring to react, washing, and distilling to obtain the diethyl acetamidomalonate. The potassium borohydride reducing agent is introduced, so that the yield of the diethyl acetamidomalonate obtained by the reaction is obviously improved.
Synthetic method of diethyl acetyl malonate
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Paragraph 0020-0047, (2020/06/05)
The invention discloses a synthetic method for diethyl acetamidomalonate. The method comprises the following steps: firstly, performing a reaction in the presence of a metal salt and a ligand to prepare a mixed liquid containing the diethyl acetamidomalonate by taking diethyl malonate and acetamide as raw materials, air as an oxidant, and acetic acid as a solvent, performing distilling, and performing repeated extraction and recrystallization to obtain the diethyl acetamidomalonate in a white crystalline powder state. The method has the advantages that the metal salt and the ligand are cheap and easy to obtain, after the reaction is finished, the metal salt and the ligand can be further recycled through treatment, the air is taken as the oxidant, and therefore the production costs are greatly reduced; the yield of the product is more than 90%, the purity of the product is more than 99%, the conversion rates of the raw materials are high, and the reaction is complete; and the by-productis only water, no ''three waste'' (waste gas, waste water and solid waste) pollution problems exist, and the method meets environmental protection requirements.
Synthesis of new ligands for targeting the S1P1 receptor
Schilson, Stefanie S.,Keul, Petra,Shaikh, Rizwan S.,Sch?fers, Michael,Levkau, Bodo,Haufe, Günter
, p. 1011 - 1026 (2015/03/04)
Sphingosine-1-phosphate (S1P) influences various fundamental biological processes by interacting with a family of five G protein-coupled receptors (S1P1-5). FTY720, a sphingosine analogue, which was approved for treatment of relapsing forms of multiple sclerosis, is phosphorylated in vivo and acts as an agonist of four of the five S1P receptor subtypes. Starting from these lead structures we developed new agonists for the S1P1 receptor. The biological activity was tested in vivo and promising ligands were fluorinated at different positions to identify candidates for positron emission tomography (PET) imaging after [18F]-labelling. The radioligands shall enable the imaging of S1P1 receptor expression in vivo and thus may serve as novel imaging markers of S1P-related diseases.
NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
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Paragraph 0133; 0134; 0135; 0136; 0137, (2014/06/25)
The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.
Peroxisome proliferator-activated receptor-γ mediates the anti-inflammatory effect of 3-hydroxy-4-pyridinecarboxylic acid derivatives: Synthesis and biological evaluation
Brun, Paola,Dean, Annalisa,Di Marco, Valerio,Surajit, Pathak,Castagliuolo, Ignazio,Carta, Davide,Ferlin, Maria Grazia
, p. 486 - 497 (2013/06/04)
Seven 3-hydroxy-4-pyridinecarboxylic acid derivatives (HPs), aza-analogues of salicylic acid and structurally close to other potent inflammatory pyridine compounds such as aminopyridinylmethanols and aminopyridinamines, were synthesized, and their anti-inflammatory activity was evaluated. The synthesis was performed by adopting a general procedure involving an intramolecular Diels-Alder cycloaddition of oxazoles with acrylic acid to form various substituted pyridinic acids. The newly synthesized HPs did not exhibit cytotoxic activity on human monocytes-derived macrophages at concentrations up to 10 2 μM. Anti-inflammatory activity of the compounds was screened in vitro by evaluating the capability to inhibit cytokines release from lipopolysaccharide (LPS) stimulated human macrophages. 3-Hydroxy-1-methyl-4- pyridinecarboxylic acid (24) was found to be the most active HP. At 10 μM concentration, HP 24 reduced LPS-induced and nuclear factor-κB activation and cyclooxygenase-2 expression, while increased intracellular reactive oxygen species generation and peroxisome proliferator-activated receptor (PPAR-γ) mRNA transcript level. Indeed, pre-treatment of LPS-exposed human macrophages with PPAR-γ specific antagonist completely prevented HP 24-induced TNF-α and IL8 down regulation, demonstrating that the PPARγ pathway is mandatory for the HP 24 anti-inflammatory effect. Finally, daily treatment with HP 24 ameliorated the outcome of DSS-induced colitis in mice, significantly reducing colonic MPO activity and IL-1β tissue levels.
NEW LIGANDS FOR TARGETING OF S1P RECEPTORS FOR IN VIVO IMAGING AND TREATMENT OF DISEASES
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Page/Page column 16, (2013/03/26)
The present invention relates to novel compounds of formulae (I) and (II) which are useful in the prevention, treatment and diagnosis, in vivo diagnosis of diseases or disorders related to S1P receptors, in particular, in diseases which are connected to the regulatory function of sphingosine-1-phosphate (S1P) and its analogues, such as inflammation, pain, autoimmune diseases and cardiovascular diseases.
Synthesis of 3-amlno-8-azachromans and 3-amino-7-azabenzofurans via inverse electron demand dlels-alder reaction
Badarau, Eduard,Suzenet, Franck,Finaru, Adriana-Lusninita,Guillaumet, Gerald
body text, p. 3619 - 3627 (2009/12/01)
The synthesis of 3-amino-8-azachromans and 3-amino-7-azabenzofurans derivatives is reported. The synthetic strategy is based on an inverse electron demand Diels-Alder approach, which employs 1,2,4-triazines that are judiciously substituted with amino alkynols. This approach permits the variation of the substituent on the aromatic core and on the amine moiety, as well as of the size of the nonaromatic ring.
Synthetic and biotransformation studies on prochiral non-proteinogenic amino acids: Diethyl α-acetamido, α-alkylmalonates
Singh,Prasad,Errington,Belokon,Kochetkov,Saxena,Jain,Parmar
, p. 10 - 15 (2007/10/03)
Nine diethyl α-acetamido, α-alkylmalonates 3-11 (alkyl=methyl, benzyl, 3-fluorobenzyl, 4-fluorobenzyl, 2,6-difluorobenzyl, 3-trifluoromethylbenzyl, 4-trifluoromethylbenzyi, 2-chlorobenzyl and 3-chlorobenzyl) have been synthesised in three steps starting with diethyl malonate in overall yields of 49-90%. The structures of C-alkylated acetamidomalonates have been established on the basis of their speciral data, the structures of two compounds 9 and 11 are also confirmed on the basis of their X-ray crystallographic studies. Further, the X-ray crystal structure of the chiral monoethyl ester of α-acetamidomalonic acid 1 has been studied. None of our C-alkylated acetamidomalonate has been found to be a substrate for lipase-catalysed enantiodifferentiating deesterification/hydrolysis of the symmetric diester groups.
