4-(methyl(5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzoic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-(methyl(5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzoic acid
• 英文别名: 4-[Methyl-[5-methyl-4-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]amino]benzoic acid；4-[methyl-[5-methyl-4-[4-(trifluoromethoxy)phenyl]pyrimidin-2-yl]amino]benzoic acid
• 化学式: C₂₀H₁₆F₃N₃O₃
• 分子量: 403.361
• InChiKey: NPRREQOEZKWXTR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  4-(methyl(5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzoic acid 、 2,6-二甲基苯胺 在 N,N-二异丙基乙胺 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以23%的产率得到N-(2,6-dimethylphenyl)-4-(methyl(5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzamide
  参考文献：
  名称：

  The discovery of novel N-(2-pyrimidinylamino) benzamide derivatives as potent hedgehog signaling pathway inhibitors

  摘要：

  Hedgehog signaling pathway inhibitors are emerging as new therapeutic intervention against cancer. A novel series of N-(2-pyrimidinylamino) benzamide derivatives as hedgehog signaling pathway inhibitors were designed and synthesized. Most compounds presented significant inhibitory effect on hedgehog signaling pathway, among which 21 compounds exhibited more potent than vismodegib. Furthermore, compound 6a showed moderate pharmacokinetic properties in vivo, representing a promising lead compound for further exploration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.022
• 作为产物：
  描述：

  2,4-二氯-5-甲基嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 水 、 palladium diacetate 、 potassium carbonate 、 caesium carbonate 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 三乙胺 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.0h， 生成 4-(methyl(5-methyl-4-(4-(trifluoromethoxy)phenyl)pyrimidin-2-yl)amino)benzoic acid
  参考文献：
  名称：

  The discovery of novel N-(2-pyrimidinylamino) benzamide derivatives as potent hedgehog signaling pathway inhibitors

  摘要：

  Hedgehog signaling pathway inhibitors are emerging as new therapeutic intervention against cancer. A novel series of N-(2-pyrimidinylamino) benzamide derivatives as hedgehog signaling pathway inhibitors were designed and synthesized. Most compounds presented significant inhibitory effect on hedgehog signaling pathway, among which 21 compounds exhibited more potent than vismodegib. Furthermore, compound 6a showed moderate pharmacokinetic properties in vivo, representing a promising lead compound for further exploration. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.022