[4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone | 854765-99-4

• 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: [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone
• 英文别名: [4-(3-aminophenyl)-8-trifluoromethyl-quinolin-3-yl](phenyl)methanone；[4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl]-phenylmethanone
• CAS: 854765-99-4
• 化学式: C₂₃H₁₅F₃N₂O
• 分子量: 392.38
• InChiKey: VCHGHHISVVEOEI-UHFFFAOYSA-N

物化性质

• 沸点：
  580.6±50.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  56
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone 在 三乙酰氧基硼氢化钠 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 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 在 四(三苯基膦)钯 sodium carbonate 、 三氯氧磷 作用下， 以 乙醚 、 乙醇 、 甲苯 为溶剂， 反应 24.0h， 生成 [4-(3-aminophenyl)-8-(trifluoromethyl)quinolin-3-yl](phenyl)methanone
  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。
• 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。
• Further modification on phenyl acetic acid based quinolines as liver X receptor modulators
  作者：Baihua Hu、James Jetter、David Kaufman、Robert Singhaus、Ronald Bernotas、Rayomand Unwalla、Elaine Quinet、Dawn Savio、Anita Halpern、Michael Basso、James Keith、Valerie Clerin、Liang Chen、Qiang-Yuan Liu、Irene Feingold、Christine Huselton、Farooq Azam、Annika Goos-Nilsson、Anna Wilhelmsson、Ponnal Nambi、Jay Wrobel

  DOI：10.1016/j.bmc.2007.03.013

  日期：2007.5

  A series of phenyl acetic acid based quinolines was prepared as LXR modulators. An SAR study in which the C-3 and C-8 positions of the quinoline core were varied led to the identification of two potent LXR agonists 23 and 27. Both compounds displayed good binding affinity for LXR beta and LXR alpha, and increased expression of ABCAl in THP-1 cells. These two compounds also had desirable pharmacokinetic profiles in mice and displayed in vivo efficacy in a 12-week Apo E knockout mouse lesion model. (c) 2007 Elsevier Ltd. All rights reserved.
• MACROCYCLIC ISOQUINOLINE PEPTIDE INHIBITORS OF HEPATITIS C VIRUS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1629000A2

  公开（公告）日：2006-03-01
• EP1629000A4
  申请人：——

  公开号：EP1629000A4

  公开（公告）日：2006-11-29