2-(ethyl-[2]pyridyl-amino)-ethanol | 856375-38-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 2-(ethyl-[2]pyridyl-amino)-ethanol
• 英文别名: 2-(Aethyl-[2]pyridyl-amino)-aethanol；2-(N-ethyl-N-(2-pyridyl)amino)ethanol；2-[ethyl(pyridin-2-yl)amino]ethanol
• CAS: 856375-38-7
• 化学式: C₉H₁₄N₂O
• mdl: MFCD14586600
• 分子量: 166.223
• InChiKey: UTBWIAGFIFQNHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.444
• 拓扑面积：
  36.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(ethyl-[2]pyridyl-amino)-ethanol 在 四氢吡咯 、 sodium tetrahydroborate 、 CoCl₂*C₄H₈N₂O₂ 、 potassium tert-butylate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 5-[[4-[2-[Ethyl(pyridin-2-yl)amino]ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Structure-activity relationships of rosiglitazone for peroxisome proliferator-activated receptor gamma transrepression

  摘要：

  Anti-inflammatory effects of peroxisome proliferator-activated receptor gamma (PPRA gamma) ligands are thought to be largely due to PPAR gamma-mediated transrepression. Thus, transrepression-selective PPAR gamma ligands without agonistic activity or with only partial agonistic activity should exhibit anti-inflammatory properties with reduced side effects. Here, we investigated the structure-activity relationships (SARs) of PPAR gamma agonist rosiglitazone, focusing on transrepression activity. Alkenic analogs showed slightly more potent transrepression with reduced efficacy of transactivating agonistic activity. Removal of the alkyl group on the nitrogen atom improved selectivity for transrepression over transactivation. Among the synthesized compounds, 3l exhibited stronger transrepressional activity (IC50: 14 mu M) and weaker agonistic efficacy (11%) than rosiglitazone or pioglitazone. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.04.061
• 作为产物：
  描述：

  2-溴吡啶 、 N-乙基乙醇胺 生成 2-(ethyl-[2]pyridyl-amino)-ethanol
  参考文献：
  名称：

  N-2-PYRIDYLALKANOLAMINES AND ESTERS

  摘要：

  DOI：

  10.1021/jo01157a021

文献信息

• Process for the preparation of substituted phenyl ether compounds
  申请人：Ludescher Johannes

  公开号：US20090149508A1

  公开（公告）日：2009-06-11

  A novel process for the preparation of a compound of the formula (II), which is useful as intermediate compound for the preparation of thiazolidinedione derivatives, such as rosiglitazone, pioglitazone, troglitazone and ciglitazone, is disclosed.

  本发明公开了一种制备化合物（II）的新工艺，该化合物可用作噻唑烷二酮衍生物的中间化合物，例如罗格列酮、派格列酮、曲格列酮和西格列酮。
• A PROCESS FOR THE PREPARATION OF SUBSTITUTED PHENYL ETHER COMPOUNDS AND ROSIGLITAZONE
  申请人：SANDOZ AG

  公开号：EP1910294A1

  公开（公告）日：2008-04-16
• [EN] A PROCESS FOR THE PREPARATION OF SUBSTITUTED PHENYL ETHER COMPOUNDS AND ROSIGLITAZONE<br/>[FR] PROCEDE DE PREPARATION DE COMPOSES DE PHENYLETHER SUBSTITUES ET DE ROSIGLITAZONE
  申请人：SANDOZ AG

  公开号：WO2007017095A1

  公开（公告）日：2007-02-15

  [EN] A novel process for the preparation of a compound of the formula (II), which is useful as intermediate compound for the preparation of thiazolidinedione derivatives, such as rosiglitazone, pioglitazone, troglitazone and ciglitazone, is disclosed. The novel process comprising reacting a compound of the formula (III) with a compound of the formula (IV) in a mixture of a non-polar water immiscible organic solvent and water (two phase system) with an alkali metal hydroxide or an alkali metal carbonate as a base in the presence of a phase transfer catalyst. In the first aspect of the present invention comprising reacting 2-(N-methyl-N-(2- pyridyl) ethanol with 4-fluorobenzaldehyde in the mixture of a non-polar water immiscible organic solvent, preferably toluene, and water with an alkali metal hydroxide or an alkali metal carbonate as a base, preferably potassium hydroxide, in the presence of a phase transfer catalyst, e.g. tetra n-butylammonium hydrogensulphate or benzyltriethylammonium chloride, to obtain 4-[2-(N-methyl-N-(2- pyridyl)amino)ethoxy]benzaldehyde, which is the key intermediate for preparing rosiglitazone and its salts, e.g. maleate salt or phosphate salt, useful in the treatment of Type II diabetes.
  [FR] L'invention concerne un nouveau procédé pour la préparation d'un composé de formule (II) utile comme composé intermédiaire pour la préparation de dérivés de thiazolidinedione, tels que la rosiglitazone, la pioglitazone, la troglitazone et la ciglitazone. Ce nouveau procédé consiste à faire réagir un composé de formule (III) avec un composé de formule (IV) dans un mélange d'un solvant organique non polaire non miscible avec l'eau et d'eau (système diphasique) avec un hydroxyde de métal alcalin ou un carbonate de métal alcalin sous forme de base en présence d'un catalyseur de transfert de phase. Dans le premier aspect de la présente invention, le procédé consiste à faire réagir du 2-(N-méthyl-N-(2-pyridyl)éthanol avec du 4-fluorobenzaldhéhyde dans le mélange d'un solvant organique non polaire non miscible avec l'eau, de préférence du toluène, et d'eau avec un hydroxyde de métal alcalin ou un carbonate de métal alcalin sous forme base, de préférence de l'hydroxyde de potassium, en présence d'un catalyseur de transfert de phase, tel que le sulfate d'hydrogène de tétra-n-butylammonium ou le chlorure de benzyltriéthylammonium, en vue de l'obtention d'un 4-[2-(N-méthyl-N-(2- pyridyl)amino)éthoxy]benzaldéhyde, qui est le composé intermédiaire principal pour préparer la rosiglitazone et ses sels, tels que le sel de maléate ou le sel de phosphate, utiles dans le traitement du diabète de type II.
• N-2-PYRIDYLALKANOLAMINES AND ESTERS
  作者：NATHAN WEINER、IRVING ALLAN KAYE

  DOI：10.1021/jo01157a021

  日期：1949.9
• Structure-activity relationships of rosiglitazone for peroxisome proliferator-activated receptor gamma transrepression
  作者：Yosuke Toyota、Sayaka Nomura、Makoto Makishima、Yuichi Hashimoto、Minoru Ishikawa

  DOI：10.1016/j.bmcl.2017.04.061

  日期：2017.6

  Anti-inflammatory effects of peroxisome proliferator-activated receptor gamma (PPRA gamma) ligands are thought to be largely due to PPAR gamma-mediated transrepression. Thus, transrepression-selective PPAR gamma ligands without agonistic activity or with only partial agonistic activity should exhibit anti-inflammatory properties with reduced side effects. Here, we investigated the structure-activity relationships (SARs) of PPAR gamma agonist rosiglitazone, focusing on transrepression activity. Alkenic analogs showed slightly more potent transrepression with reduced efficacy of transactivating agonistic activity. Removal of the alkyl group on the nitrogen atom improved selectivity for transrepression over transactivation. Among the synthesized compounds, 3l exhibited stronger transrepressional activity (IC50: 14 mu M) and weaker agonistic efficacy (11%) than rosiglitazone or pioglitazone. (C) 2017 Elsevier Ltd. All rights reserved.