5-bromo-2-chloro-N-(4-(trifluoromethoxy)phenyl)pyrimidin-4-amine

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-bromo-2-chloro-N-(4-(trifluoromethoxy)phenyl)pyrimidin-4-amine
• 英文别名: 5-bromo-2-chloro-N-[4-(trifluoromethoxy)phenyl]pyrimidin-4-amine
• 化学式: C₁₁H₆BrClF₃N₃O
• 分子量: 368.54
• InChiKey: MIKKMQOXKFVWGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  47
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-bromo-2-chloro-N-(4-(trifluoromethoxy)phenyl)pyrimidin-4-amine 在 copper(l) iodide 、 trans-bis(triphenylphosphine)palladium dichloride 、 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 9.0h， 生成 N-(3-methoxy-5-(4-(pyrrolidin-1-yl)piperidin-1-yl)phenyl)-7-(4-(trifluoromethoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
  参考文献：
  名称：

  Structure-activity relationship of 7-aryl-2-anilino-pyrrolopyrimidines as Mer and Axl tyrosine kinase inhibitors

  摘要：

  The TAM (Axl, Mer, and Tyro3) family is implicated in the survival and chemoresistance of tumours and has emerged as a potential therapeutic target. A novel series of 7-aryl-2-anilino-pyrrolopyrimidines were identified as potent Axl/Mer tyrosine kinase inhibitors without significant inhibition of Tyro3. A representative compound27exhibited IC(50)values of 2 nM and 16 nM for Mer and Axl, respectively, and considerable inhibition for Mer phosphorylation in cells. Docking studies suggested that the formation of a salt bridge between the nitrogen of the aniline moiety with ASP678 of the Mer kinase domain as well as an interaction with the hinge region that most kinase inhibitors have in common would be essential to retain activity. These results could provide useful information for finding promising inhibitors of Axl/Mer for the treatment of cancer.

  DOI：

  10.1080/14756366.2020.1825407
• 作为产物：
  描述：

  5-溴-2,4-二氯嘧啶 、 对三氟甲氧基苯胺 在 三乙胺 作用下， 以 异丙醇 为溶剂， 反应 12.0h， 以89%的产率得到5-bromo-2-chloro-N-(4-(trifluoromethoxy)phenyl)pyrimidin-4-amine
  参考文献：
  名称：

  Structure-activity relationship of 7-aryl-2-anilino-pyrrolopyrimidines as Mer and Axl tyrosine kinase inhibitors

  摘要：

  The TAM (Axl, Mer, and Tyro3) family is implicated in the survival and chemoresistance of tumours and has emerged as a potential therapeutic target. A novel series of 7-aryl-2-anilino-pyrrolopyrimidines were identified as potent Axl/Mer tyrosine kinase inhibitors without significant inhibition of Tyro3. A representative compound27exhibited IC(50)values of 2 nM and 16 nM for Mer and Axl, respectively, and considerable inhibition for Mer phosphorylation in cells. Docking studies suggested that the formation of a salt bridge between the nitrogen of the aniline moiety with ASP678 of the Mer kinase domain as well as an interaction with the hinge region that most kinase inhibitors have in common would be essential to retain activity. These results could provide useful information for finding promising inhibitors of Axl/Mer for the treatment of cancer.

  DOI：

  10.1080/14756366.2020.1825407