2-benzoyl-3-(2-trifluoromethylphenylamino)acrylic acid ethyl ester | 854777-97-2

• 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: 2-benzoyl-3-(2-trifluoromethylphenylamino)acrylic acid ethyl ester
• 英文别名: ethyl-2-benzoyl-3-[2-(trifluoromethyl)phenylamino]acrylate；ethyl 2-benzoyl-3-[2-(trifluoromethyl)anilino]prop-2-enoate
• CAS: 854777-97-2
• 化学式: C₁₉H₁₆F₃NO₃
• 分子量: 363.336
• InChiKey: LWRDAHYVXKWFSZ-UHFFFAOYSA-N

物化性质

• 沸点：
  441.6±45.0 °C(Predicted)
• 密度：
  1.291±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.45
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  55.4
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  2-benzoyl-3-(2-trifluoromethylphenylamino)acrylic acid ethyl ester 在 四(三苯基膦)钯 三乙酰氧基硼氢化钠 、 sodium carbonate 、 溶剂黄146 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 8.0h， 生成 (4-{[{3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}(methyl)amino]methyl}phenyl)acetic acid
  参考文献：
  名称：

  Discovery of Phenyl Acetic Acid Substituted Quinolines as Novel Liver X Receptor Agonists for the Treatment of Atherosclerosis

  摘要：

  A structure-based approach was used to optimize our new class of quinoline LXR modulators leading to phenyl acetic acid substituted quinolines 15 and 16. Both compounds displayed good binding affinity for LXR beta and LXR alpha and were potent activators in LBD transactivation assays. The compounds also increased expression of ABCA1 and stimulated cholesterol efflux in THP-1 cells. Quinoline 16 showed good oral bioavailability and in vivo efficacy in a LDLr knockout mouse model for lesions.

  DOI：

  10.1021/jm0609566
• 作为产物：
  描述：

  邻氨基三氟甲苯 、 ethoxymethylene-benzoylacetic acid,ethyl ester 以 甲苯 为溶剂， 反应 18.0h， 以82%的产率得到2-benzoyl-3-(2-trifluoromethylphenylamino)acrylic acid ethyl ester
  参考文献：
  名称：

  Quinolines useful in treating cardiovascular disease

  摘要：

  本发明提供了式I化合物的用途，它们在治疗或抑制LXR介导的疾病中是有用的。

  公开号：

  US20050131014A1

文献信息

• QUINOLINE COMPOUNDS
  申请人：KOURA Minoru

  公开号：US20100016327A1

  公开（公告）日：2010-01-21

  [Object] To provide a novel LXRβ agonist that is useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. [Solving Means] A quinoline compound represented by the following general formula (1) or salt thereof, or their solvate.

  提供一种新型的LXRβ激动剂，可用作预防和/或治疗动脉粥样硬化；动脉硬化，如糖尿病引起的动脉硬化；血脂异常；高胆固醇血症；与脂质相关的疾病；由炎症性细胞因子引起的炎症性疾病；过敏性皮肤病；糖尿病；或阿尔茨海默病的治疗剂。通过以下一般式（1）表示的喹啉化合物或其盐，或它们的溶剂化合物。
• Quinoline compounds
  申请人：Kowa Company, Ltd.

  公开号：US08008306B2

  公开（公告）日：2011-08-30

  To provide a novel LXRβ agonist that is useful as a preventative and/or therapeutic agent for atherosclerosis; arteriosclerosis such as those resulting from diabetes; dyslipidemia; hypercholesterolemia; lipid-related diseases; inflammatory diseases that are caused by inflammatory cytokines; skin diseases such as allergic skin diseases; diabetes; or Alzheimer's disease. A quinoline compound represented by the following general formula (1) or salt thereof, or their solvate.

  提供一种新型的LXRβ激动剂，可用作预防和/或治疗动脉粥样硬化；动脉硬化，如糖尿病引起的动脉硬化；血脂异常；高胆固醇血症；与脂类相关的疾病；由炎性细胞因子引起的炎症性疾病；过敏性皮肤病；糖尿病；或阿尔茨海默病的治疗剂。一种喹啉化合物，由下列通式（1）表示，或其盐，或其溶剂化物。
• Quinolines and pharmaceutical compositions thereof
  申请人：Wyeth

  公开号：US07576215B2

  公开（公告）日：2009-08-18

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了I式化合物，可用于治疗或抑制LXR介导的疾病。
• Quinolines useful in treating cardiovascular disease
  申请人：Collini D. Michael

  公开号：US20050131014A1

  公开（公告）日：2005-06-16

  This invention provides compounds of formula I that are useful in the treatment or inhibition of LXR mediated diseases.

  本发明提供了式I化合物的用途，它们在治疗或抑制LXR介导的疾病中是有用的。
• Discovery of Phenyl Acetic Acid Substituted Quinolines as Novel Liver X Receptor Agonists for the Treatment of Atherosclerosis
  作者：Baihua Hu、Michael Collini、Rayomand Unwalla、Christopher Miller、Robert Singhaus、Elaine Quinet、Dawn Savio、Anita Halpern、Michael Basso、James Keith、Valerie Clerin、Liang Chen、Christine Resmini、Qiang-Yuan Liu、Irene Feingold、Christine Huselton、Farooq Azam、Mathias Farnegardh、Cristofer Enroth、Tomas Bonn、Annika Goos-Nilsson、Anna Wilhelmsson、Ponnal Nambi、Jay Wrobel

  DOI：10.1021/jm0609566

  日期：2006.10.1

  A structure-based approach was used to optimize our new class of quinoline LXR modulators leading to phenyl acetic acid substituted quinolines 15 and 16. Both compounds displayed good binding affinity for LXR beta and LXR alpha and were potent activators in LBD transactivation assays. The compounds also increased expression of ABCA1 and stimulated cholesterol efflux in THP-1 cells. Quinoline 16 showed good oral bioavailability and in vivo efficacy in a LDLr knockout mouse model for lesions.