4,6-二碘-5-苄胺基嘧啶 | 754190-39-1

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4,6-二碘-5-苄胺基嘧啶
• 中文别名: N-苄基-4,6-二碘嘧啶-5-胺
• 英文名称: N-Benzyl-4,6-diiodopyrimidin-5-amine
• CAS: 754190-39-1
• 化学式: C₁₁H₉I₂N₃
• 分子量: 437.022
• InChiKey: VXNICLYOMVRJBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  16
• 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：
  37.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-二碘-5-苄胺基嘧啶 在 氨 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 14.0h， 生成 N⁵-Benzyl-6-iodo-N⁵-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：

  溴甲苯 、 4,6-二碘-5-氨基嘧啶 在 sodium hydride 、 四丁基碘化铵 作用下， 以 四氢呋喃 为溶剂， 生成 4,6-二碘-5-苄胺基嘧啶
  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

• Synthesis and biological evaluation of pteridine and pyrazolopyrimidine based adenosine kinase inhibitors
  作者：Arthur Gomtsyan、Stanley Didomenico、Chih-Hung Lee、Andrew O Stewart、Shripad S Bhagwat、Elizabeth A Kowaluk、Michael F Jarvis

  DOI：10.1016/j.bmcl.2004.06.029

  日期：2004.8

  alkynylpyrimidine classes of nonnucleoside adenosine kinase inhibitors 2 and 3. 4-Amino-substituted pteridines 8a-e were generally less active than corresponding 5- and 6-substituted pyridopyrimidines 2. Pyrazolopyrimidine 13c with IC(50)=7.5 nM was superior to its open chain alkynylpyrimidine analog 13g (IC(50)=22 nM) while pyrrolopyrimidines such as 17a were inactive.

  已测试了三种新方法来修饰非核苷腺苷激酶抑制剂2和3的现有吡啶并嘧啶和炔基嘧啶类。4-氨基取代的蝶啶8a-e的活性通常不及相应的5和6取代的吡啶并嘧啶2。 （50）= 7.5 nM优于其开链炔基嘧啶类似物13g（IC（50）= 22 nM），而吡咯并嘧啶类化合物（例如17a）没有活性。
• 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.