(4-{3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}phenyl)methanol | 854777-20-1

• 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-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}phenyl)methanol
• 英文别名: Biarylether alcohol quinoline, 5d；[4-[3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy]phenyl]methanol
• CAS: 854777-20-1
• 化学式: C₂₉H₂₀F₃NO₂
• 分子量: 471.479
• InChiKey: KKPXMFGSPSGBQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  35
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  42.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenol 、 4-羟甲基苯硼酸 在 copper diacetate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以44%的产率得到(4-{3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenoxy}phenyl)methanol
  参考文献：
  名称：

  4-(3-Aryloxyaryl)quinoline alcohols are liver X receptor agonists

  摘要：

  A series of 4-(3-aryloxyaryl)quinolines with alcohol substituents on the terminal aryl ring was prepared as potential LXR agonists, in which an alcohol group replaced an amide in previously reported amide analogs. High affinity LXR ligands with excellent agonist potency and efficacy in a functional model of LXR activity were identified, demonstrating that alcohols can substitute for amides while retaining LXR activity. The most potent compound was 5b which had an IC50 = 3.3 nM for LXR beta binding and EC50 = 12 nM (122% efficacy relative to T0901317) in an ABCA1 mRNA induction assay in J774 mouse cells. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.10.001

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。
• US7576215B2
  申请人：——

  公开号：US7576215B2

  公开（公告）日：2009-08-18
• 4-(3-Aryloxyaryl)quinoline alcohols are liver X receptor agonists
  作者：Ronald C. Bernotas、David H. Kaufman、Robert R. Singhaus、John Ullrich、Rayomand Unwalla、Elaine Quinet、Ponnal Nambi、Anna Wilhelmsson、Annika Goos-Nilsson、Jay Wrobel

  DOI：10.1016/j.bmc.2009.10.001

  日期：2009.12

  A series of 4-(3-aryloxyaryl)quinolines with alcohol substituents on the terminal aryl ring was prepared as potential LXR agonists, in which an alcohol group replaced an amide in previously reported amide analogs. High affinity LXR ligands with excellent agonist potency and efficacy in a functional model of LXR activity were identified, demonstrating that alcohols can substitute for amides while retaining LXR activity. The most potent compound was 5b which had an IC50 = 3.3 nM for LXR beta binding and EC50 = 12 nM (122% efficacy relative to T0901317) in an ABCA1 mRNA induction assay in J774 mouse cells. (C) 2009 Elsevier Ltd. All rights reserved.