3-chloro-5-bromo-7-trifluoromethylquinoxaline | 1123738-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-chloro-5-bromo-7-trifluoromethylquinoxaline
• 英文别名: 8-bromo-2-chloro-6-(trifluoromethyl)quinoxaline
• CAS: 1123738-13-5
• 化学式: C₉H₃BrClF₃N₂
• 分子量: 311.488
• InChiKey: FDLVBBQLUVHGEE-UHFFFAOYSA-N

物化性质

• 沸点：
  302.3±37.0 °C(Predicted)
• 密度：
  1.814±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  25.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-chloro-5-bromo-7-trifluoromethylquinoxaline 在 tris-(dibenzylideneacetone)dipalladium(0) 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 生成 3-((3-(4-Methylpiperazin-1-yl)-7-(trifluoromethyl)quinoxalin-5-ylamino)methyl)benzamide
  参考文献：
  名称：

  Discovery of a novel series of quinoxalines as inhibitors of c-Met kinase

  摘要：

  A series of quinoxaline inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and optimisation of the series was performed on the basis of this structure. Future directions for development of the series are discussed together with the identification of a novel quinoline scaffold.

  DOI：

  10.1016/j.bmcl.2008.11.062
• 作为产物：
  描述：

  8-bromo-6-(trifluoromethyl)quinoxalin-2-ol 在 三氯氧磷 作用下， 生成 3-chloro-5-bromo-7-trifluoromethylquinoxaline
  参考文献：
  名称：

  Discovery of a novel series of quinoxalines as inhibitors of c-Met kinase

  摘要：

  A series of quinoxaline inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and optimisation of the series was performed on the basis of this structure. Future directions for development of the series are discussed together with the identification of a novel quinoline scaffold.

  DOI：

  10.1016/j.bmcl.2008.11.062

文献信息

• Multisubstituted quinoxalines and pyrido[2,3-d]pyrimidines: Synthesis and SAR study as tyrosine kinase c-Met inhibitors
  作者：Kui Wu、Jing Ai、Qiufeng Liu、TianTian Chen、Ailing Zhao、Xia Peng、Yuanxiang Wang、Yinchun Ji、Qizheng Yao、Yechun Xu、Meiyu Geng、Ao Zhang

  DOI：10.1016/j.bmcl.2012.08.075

  日期：2012.10

  Two series of new analogues were designed by replacing the quinoline scaffold of our earlier lead 2 (zgwatinib) with quinoxaline and pyrido[2,3-d]pyrimidine frameworks. Moderate c-Met inhibitory activity was observed in the quinoxaline series. Among the pyrido[2,3-d]pyrimidine series, compounds 13a–c possessing an O-linkage were inactive, whilst the N-linked analogues 15a–c retained c-Met inhibitory

  通过用喹喔啉和吡啶并[2,3- d ]嘧啶骨架取代我们较早的铅2（zgwatinib）的喹啉支架，设计了两个系列的新类似物。在喹喔啉系列中观察到中等的c-Met抑制活性。在吡啶并[2,3- d ]嘧啶系列中，具有O-键的化合物13a - c无活性，而与N-连接的类似物15a - c保留c-Met抑制能力。在3-硝基苄基类似物15b中观察到最高的活性，其IC 50值为6.5 nM。正在对该化合物进行进一步的结构修饰。
• Discovery of a novel series of quinoxalines as inhibitors of c-Met kinase
  作者：John Porter、Simon Lumb、Fabien Lecomte、James Reuberson、Anne Foley、Mark Calmiano、Kelly le Riche、Helen Edwards、Jean Delgado、Richard J. Franklin、Jose M. Gascon-Simorte、Alison Maloney、Christoph Meier、Mark Batchelor

  DOI：10.1016/j.bmcl.2008.11.062

  日期：2009.1

  A series of quinoxaline inhibitors of c-Met kinase is described. The postulated binding mode was confirmed by an X-ray crystal structure and optimisation of the series was performed on the basis of this structure. Future directions for development of the series are discussed together with the identification of a novel quinoline scaffold.