5-[3-(4-Bromophenyl)propyl]-6-iodopyrimidin-4-amine | 454685-50-8

• 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: 5-[3-(4-Bromophenyl)propyl]-6-iodopyrimidin-4-amine
• CAS: 454685-50-8
• 化学式: C₁₃H₁₃BrIN₃
• 分子量: 418.075
• InChiKey: KEXKXFPHEGVGGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  51.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-吗啉)-5-乙炔吡啶 、 5-[3-(4-Bromophenyl)propyl]-6-iodopyrimidin-4-amine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 乙腈 为溶剂， 以40%的产率得到5-[3-(4-Bromo-phenyl)-propyl]-6-(6-morpholin-4-yl-pyridin-3-ylethynyl)-pyrimidin-4-ylamine
  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：

  5-烯丙基-4,6-二氯嘧啶 在 platinum on activated charcoal 四(三苯基膦)钯 、 氨 、 氢碘酸 、 氢气 、 N,N-二异丙基乙胺 、 三(邻甲基苯基)磷 、 sodium iodide 作用下， 以 1,4-二氧六环 、 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 70.0~100.0 ℃ 、405.3 kPa 条件下， 反应 16.0h， 生成 5-[3-(4-Bromophenyl)propyl]-6-iodopyrimidin-4-amine
  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