6-Iodo-N⁵-methyl-N⁵-(2-trifluoromethyl-benzyl)-pyrimidine-4,5-diamine | 454685-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 6-Iodo-N⁵-methyl-N⁵-(2-trifluoromethyl-benzyl)-pyrimidine-4,5-diamine
• 英文别名: 6-iodo-5-N-methyl-5-N-[[2-(trifluoromethyl)phenyl]methyl]pyrimidine-4,5-diamine
• CAS: 454685-68-8
• 化学式: C₁₃H₁₂F₃IN₄
• 分子量: 408.165
• InChiKey: CFLYWEFGYWOEPC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-(4-吗啉)-5-乙炔吡啶 、 6-Iodo-N⁵-methyl-N⁵-(2-trifluoromethyl-benzyl)-pyrimidine-4,5-diamine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 以68%的产率得到5-N-methyl-6-[2-(6-morpholin-4-ylpyridin-3-yl)ethynyl]-5-N-[[2-(trifluoromethyl)phenyl]methyl]pyrimidine-4,5-diamine
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors

  摘要：

  Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.

  DOI：

  10.1021/jm020049a
• 作为产物：
  描述：

  (4,6-Diiodo-pyrimidin-5-yl)-methyl-(2-trifluoromethyl-benzyl)-amine 在 氨 作用下， 以 乙醇 为溶剂， 生成 6-Iodo-N⁵-methyl-N⁵-(2-trifluoromethyl-benzyl)-pyrimidine-4,5-diamine
  参考文献：
  名称：

  Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors

  摘要：

  Adenosine (ADO) is an extracellular signaling molecule within the central and peripheral nervous system. Its concentration is increased at sites of tissue injury and inflammation. One of the mechanisms by which antinociceptive and antiinflammatory effects of ADO can be enhanced consists of inhibition of adenosine kinase (AK), the primary metabolic enzyme for ADO. Novel nonnucleoside AK inhibitors based on 4-amino-6-alkynylpyrimidines were prepared, and the importance of the length of the linker at the 5-position for high affinity AK inhibition was demonstrated. Compounds with 2- and 3-atom linkers were the most potent AK inhibitors. Optimization of their physicochemical properties led to 31a and 37a that effectively reduced pain and inflammation in animal models.

  DOI：

  10.1021/jm020049a