Methyl 4-{3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxymethyl}benzoate | 912553-39-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: Methyl 4-{3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxymethyl}benzoate
• 英文别名: methyl 4-[[3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]methyl]benzoate
• CAS: 912553-39-0
• 化学式: C₃₂H₂₂F₃NO₄
• 分子量: 541.526
• InChiKey: DYXKUMACGJLDGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4-{3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxymethyl}benzoate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以1.0 g的产率得到4-({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}methyl)benzoic 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 在 四(三苯基膦)钯 potassium phosphate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 乙醚 、 N,N-二甲基甲酰胺 、 丙酮 、 甲苯 为溶剂， 反应 45.0h， 生成 Methyl 4-{3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenoxymethyl}benzoate
  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

文献信息

• 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.