ethyl 3-{[1-(2-hydroxyethyl)cyclopropyl]amino}-2-(2,3,4,5-tetrafluorobenzoyl)acrylate | 1132814-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 3-{[1-(2-hydroxyethyl)cyclopropyl]amino}-2-(2,3,4,5-tetrafluorobenzoyl)acrylate
• 英文别名: ethyl 3-[1-(2-hydroxyethyl)cyclopropylamino]-2-(2,3,4,5,-tetrafluorobenzoyl)acrylate；ethyl 3-[[1-(2-hydroxyethyl)cyclopropyl]amino]-2-(2,3,4,5-tetrafluorobenzoyl)prop-2-enoate
• CAS: 1132814-42-6
• 化学式: C₁₇H₁₇F₄NO₄
• 分子量: 375.32
• InChiKey: NBJCLQCAFKWXKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.38
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 3-{[1-(2-hydroxyethyl)cyclopropyl]amino}-2-(2,3,4,5-tetrafluorobenzoyl)acrylate 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以61%的产率得到ethyl 10',11'-difluoro-2',3'-dihydro-8'-oxospiro[cyclopropane-1,4'-[4H,8H]pyrido[1,2,3-ef][1,4]benzoxazepine]-7'-carboxylate
  参考文献：
  名称：

  [EN] SPIROCYCLIC AMINOQUINOLONES AS GSK-3 INHIBITORS
  [FR] AMINOQUINOLONES SPIROCYCLIQUES UTILISÉES EN TANT QU'INHIBITEURS DE GSK-3

  摘要：

  本文提供了化学式I的螺环氨基喹啉类化合物和含有这些化合物的组合物。本文提供的化合物和组合物可用于预防、改善或治疗GSK-3抑制剂介导的疾病。在化学式(I)中：X1为O或NR8；A为键或取代或未取代的C1-C2烷基，其中取代基在存在时来自于一个到四个Q2基团；其中Q2为烷基或卤代烷基；p为0或1；q为0到2的整数。

  公开号：

  WO2009035684A1
• 作为产物：
  描述：

  左氧氟单酯 在 乙酸酐 作用下， 以 甲苯 为溶剂， 反应 8.0h， 生成 ethyl 3-{[1-(2-hydroxyethyl)cyclopropyl]amino}-2-(2,3,4,5-tetrafluorobenzoyl)acrylate
  参考文献：
  名称：

  Quinolone derivatives containing strained spirocycle as orally active glycogen synthase kinase 3β (GSK-3β) inhibitors for type 2 diabetics

  摘要：

  The design, synthesis, and evaluation of 6-6-7 tricyclic quinolones containing the strained spirocycle moiety aiming at the GSK-3 beta inhibitor were described. Among the synthesized compounds, 44, having a cyclobutane ring on a spirocycle, showed excellent GSK-3b inhibitory activity in both cell-free and cell-based assays (IC50 = 36 nM, EC50 = 3.2 mu M, respectively). Additionally, 44 decreased the plasma glucose concentration dose-dependently after an oral glucose tolerance test in mice. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.12.046

文献信息

• Spirocyclic aminoquinolones as GSK-3 inhibitors
  申请人：Kyorin Pharmaceutical Co., Ltd.

  公开号：US08901112B2

  公开（公告）日：2014-12-02

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK-3 inhibitors mediated diseases.

  本文提供了公式I的螺环氨基喹啉和含有该化合物的组合物。本文提供的化合物和组合物在预防、改善或治疗GSK-3抑制剂介导的疾病方面具有用处。
• SPIROCYCLIC AMINOQUINOLONES AS GSK-3 INHIBITORS
  申请人：KYORIN PHARMACEUTICALS CO., LTD.

  公开号：US20140005184A1

  公开（公告）日：2014-01-02

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK-3 inhibitors mediated diseases.

  本文提供的是公式I的螺环氨基喹啉和含有这些化合物的组合物。这些化合物和组合物对预防、改善或治疗GSK-3抑制剂介导的疾病是有用的。
• Quinolone derivatives containing strained spirocycle as orally active glycogen synthase kinase 3β (GSK-3β) inhibitors for type 2 diabetics
  作者：Shigeki Seto、Kazuhiko Yumoto、Kyoko Okada、Yoshikazu Asahina、Aya Iwane、Maki Iwago、Reiko Terasawa、Kevin R. Shreder、Koji Murakami、Yasushi Kohno

  DOI：10.1016/j.bmc.2011.12.046

  日期：2012.2

  The design, synthesis, and evaluation of 6-6-7 tricyclic quinolones containing the strained spirocycle moiety aiming at the GSK-3 beta inhibitor were described. Among the synthesized compounds, 44, having a cyclobutane ring on a spirocycle, showed excellent GSK-3b inhibitory activity in both cell-free and cell-based assays (IC50 = 36 nM, EC50 = 3.2 mu M, respectively). Additionally, 44 decreased the plasma glucose concentration dose-dependently after an oral glucose tolerance test in mice. (C) 2011 Elsevier Ltd. All rights reserved.
• [EN] SPIROCYCLIC AMINOQUINOLONES AS GSK-3 INHIBITORS<br/>[FR] AMINOQUINOLONES SPIROCYCLIQUES UTILISÉES EN TANT QU'INHIBITEURS DE GSK-3
  申请人：ACTIVX BIOSCIENCES INC

  公开号：WO2009035684A1

  公开（公告）日：2009-03-19

  Provided herein are spirocyclic aminoquinolones of formula I and compositions containing the compounds. The compounds and compositions provided herein are useful in the prevention, amelioration or treatment of GSK- 3 inhibitors mediated diseases. In Formula (I): X1 is O or NR8; A is bond or substituted or unsubstituted C1-C2 alkylene, wherein the substituents when present are selected from one to four Q2 groups; where Q2 is alkyl or haloalkyl; p is 0 or 1; and q is an integer of 0 to 2.

  本文提供了化学式I的螺环氨基喹啉类化合物和含有这些化合物的组合物。本文提供的化合物和组合物可用于预防、改善或治疗GSK-3抑制剂介导的疾病。在化学式(I)中：X1为O或NR8；A为键或取代或未取代的C1-C2烷基，其中取代基在存在时来自于一个到四个Q2基团；其中Q2为烷基或卤代烷基；p为0或1；q为0到2的整数。