4,6-二氯-5-[3-(4-甲氧基-苯基)-丙基]-嘧啶 | 1027581-91-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 4,6-二氯-5-[3-(4-甲氧基-苯基)-丙基]-嘧啶
• 英文名称: 4,6-Dichloro-5-[3-(4-methoxyphenyl)propyl]pyrimidine
• CAS: 1027581-91-4
• 化学式: C₁₄H₁₄Cl₂N₂O
• 分子量: 297.184
• InChiKey: SSAKQVUTCZNKMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  35
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-二氯-5-[3-(4-甲氧基-苯基)-丙基]-嘧啶 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 氨 、 氢碘酸 、 三乙胺 、 sodium iodide 作用下， 以 乙醇 、 丙酮 、 乙腈 为溶剂， 生成 5-[3-(4-Methoxy-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：

  烯丙基丙二酸二乙酯 在 palladium on activated charcoal 三正丁胺 、 氢气 、 sodium ethanolate 、 palladium diacetate 、 三氯氧磷 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 19.0h， 生成 4,6-二氯-5-[3-(4-甲氧基-苯基)-丙基]-嘧啶
  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

文献信息

• Design, Synthesis, and Structure−Activity Relationship of 6-Alkynylpyrimidines as Potent Adenosine Kinase Inhibitors
  作者：Arthur Gomtsyan、Stanley Didomenico、Chih-Hung Lee、Mark A. Matulenko、Ki Kim、Elizabeth A. Kowaluk、Carol T. Wismer、Joe Mikusa、Haixia Yu、Kathy Kohlhaas、Michael F. Jarvis、Shripad S. Bhagwat

  DOI：10.1021/jm020049a

  日期：2002.8.1

  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.