4,6-dihydroxy-5-(3-bromobenzyl)pyrimidine | 454685-21-3

• 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: 4,6-dihydroxy-5-(3-bromobenzyl)pyrimidine
• 英文别名: 5-[(3-bromophenyl)methyl]-4-hydroxy-1H-pyrimidin-6-one
• CAS: 454685-21-3
• 化学式: C₁₁H₉BrN₂O₂
• 分子量: 281.109
• InChiKey: IVWKBCHDJDWWSL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  61.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-dihydroxy-5-(3-bromobenzyl)pyrimidine 在 三氯氧磷 作用下， 反应 16.0h， 以77%的产率得到4,6-dichloro-5-(3-bromobenzyl)pyrimidine
  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：

  3-溴苄溴 在 sodium ethanolate 、 sodium 作用下， 以 乙醇 为溶剂， 反应 32.58h， 生成 4,6-dihydroxy-5-(3-bromobenzyl)pyrimidine
  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

• [EN] FUNGICIDAL BENZYLPYRIMIDINE DERIVATIVES<br/>[FR] DÉRIVÉS FONGICIDES DE BENZYLPYRIMIDINE
  申请人：BAYER CROPSCIENCE AG

  公开号：WO2006136327A1

  公开（公告）日：2006-12-28

  [EN] Novel benzylpyrimidine derivatives of the formula (I) wherein, R represents C_2-6 alkyl, X represents halogen, Y represents halogen, and n is an integer of 0 to 2, when n is 2 the two Y radicals may be the same or different from each other, and the use of the new compounds as fungicides.
  [FR] La présente invention concerne de nouveaux dérivés de benzylpyrimidine de formule (I) où R représente un groupe alkyle en C₂ à C₆, X représente un halogène, Y représente un halogène et n est un nombre entier de 0 à 2 où, lorsque n vaut 2, les deux radicaux Y peuvent être identiques ou différents l'un de l'autre, ainsi que l'utilisation des nouveaux composés comme fongicides.
• 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.