3-bromo-8-(trifluoromethyl)quinolin-4-ol | 854778-26-0

• 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: 3-bromo-8-(trifluoromethyl)quinolin-4-ol
• 英文别名: 3-Bromo-4-hydroxy-8-trifluoromethylquinoline；3-bromo-8-(trifluoromethyl)-1H-quinolin-4-one
• CAS: 854778-26-0
• 化学式: C₁₀H₅BrF₃NO
• 分子量: 292.055
• InChiKey: YIVXMXIGZYUWAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-bromo-8-(trifluoromethyl)quinolin-4-ol 在 四(三苯基膦)钯 碳酸氢钠 、 sodium carbonate 、 potassium carbonate 、 三溴氧磷 作用下， 以 甲醇 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.0h， 生成 methyl {4-[({3-[3-phenyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate
  参考文献：
  名称：

  Further modification on phenyl acetic acid based quinolines as liver X receptor modulators

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.03.013
• 作为产物：
  描述：

  8-(三氟甲基)喹啉-4(1H)-酮 在 溴 、 溶剂黄146 作用下， 反应 0.5h， 以83%的产率得到3-bromo-8-(trifluoromethyl)quinolin-4-ol
  参考文献：
  名称：

  Further modification on phenyl acetic acid based quinolines as liver X receptor modulators

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.03.013

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。
• Click chemistry approach: Regioselective one-pot synthesis of some new 8-trifluoromethylquinoline based 1,2,3-triazoles as potent antimicrobial agents
  作者：B. Garudachari、Arun M. Isloor、M.N. Satyanarayana、Hoong-Kun Fun、Gurumurthy Hegde

  DOI：10.1016/j.ejmech.2014.01.008

  日期：2014.3

  synthesized by multi-step reactions by click chemistry approach. Synthesized compounds were characterized by spectral studies and X-ray analysis. The final compounds were screened for their in-vitro antimicrobial activity by well plate method (zone of inhibition). Compounds 5c, 6b, 8b, 11 and 12 were found to be active against tested microbial strains. The results are summarized in Tables 5 and 6.

  通过点击化学方法，通过多步反应合成了三组基于8-三氟甲基喹啉的1,2,3-三唑衍生物（5a – c，6a – d和7a – c）。合成的化合物通过光谱研究和X射线分析进行表征。通过孔板法（抑制区）筛选最终化合物的体外抗菌活性。发现化合物5c，6b，8b，11和12对测试的微生物菌株具有活性。结果总结在表5和6中。
• 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：Wyeth, A Corporation of the State of Delaware

  公开号：EP1692111A2

  公开（公告）日：2006-08-23
• US7576215B2
  申请人：——

  公开号：US7576215B2

  公开（公告）日：2009-08-18