6-(2-hydroxyethyl)thymine

• 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: 6-(2-hydroxyethyl)thymine
• 英文别名: 6-(2-hydroxyethyl)-5-methyl-1H-pyrimidine-2,4-dione
• 化学式: C₇H₁₀N₂O₃
• 分子量: 170.168
• InChiKey: AMLLJUPUFWNFJH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  78.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2,4-dimethoxy-6-(2-hydroxyethyl)-5-methylpyrimidine 在 氨 作用下， 以 甲醇 为溶剂， 反应 43.0h， 生成 6-(2-hydroxyethyl)thymine
  参考文献：
  名称：

  Synthesis of C-6 Pyrimidine Acyclic Nucleoside Analogs as Potential Antiviral Agents

  摘要：

  A number of pyrimidine acyclic nucleosides in which the acyclic moiety is attached to the C-6 position rather than N-1 of the pyrimidine ring have been prepared. This was accomplished via treatment of lithiated 2,4-methoxy-5,6-dimethylpyrimidine, or, 2,4-dimethoxy-6-methylpyrimidine with 1,3-bis-(benzyloxy)-2-propanone, benzyl chloromethyl ether or oxirane, respectively, to give the corresponding key intermediates 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4- dimethoxy-5-methylpyrimidine (2a), 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4-dimethoxypyrimidine (2b), 6-(2-benzyloxyethyl)-2,4-dimethoxy-5-methylpyrimidine (3), and 2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine (4a). After acidic hydrolysis, followed by debenzylation with boron trichloride these key intermediates were converted to the target C-6 pyrimidine acyclic derivatives. Compounds 6-8b, 11-13, 15, 16, 20, 22, 26, and 29-32 were evaluated for activity against herpes viruses and human immunodeficiency virus. None of the compounds were active against the viruses nor were they cytotoxic at the highest concentration tested.

  DOI：

  10.1080/15257779408013263

文献信息

• Synthesis of C-6 Pyrimidine Acyclic Nucleoside Analogs as Potential Antiviral Agents
  作者：Ling-Yih Hsu、Dean S. Wise、William M. Shannon、John C. Drach、Leroy B. Townsend

  DOI：10.1080/15257779408013263

  日期：1994.3

  A number of pyrimidine acyclic nucleosides in which the acyclic moiety is attached to the C-6 position rather than N-1 of the pyrimidine ring have been prepared. This was accomplished via treatment of lithiated 2,4-methoxy-5,6-dimethylpyrimidine, or, 2,4-dimethoxy-6-methylpyrimidine with 1,3-bis-(benzyloxy)-2-propanone, benzyl chloromethyl ether or oxirane, respectively, to give the corresponding key intermediates 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4- dimethoxy-5-methylpyrimidine (2a), 6-[3-benzyloxy-2-[(benzyloxy)methyl]-2-hydroxypropyl]-2,4-dimethoxypyrimidine (2b), 6-(2-benzyloxyethyl)-2,4-dimethoxy-5-methylpyrimidine (3), and 2,4-dimethoxy-6-(3-hydroxypropyl)-5-methylpyrimidine (4a). After acidic hydrolysis, followed by debenzylation with boron trichloride these key intermediates were converted to the target C-6 pyrimidine acyclic derivatives. Compounds 6-8b, 11-13, 15, 16, 20, 22, 26, and 29-32 were evaluated for activity against herpes viruses and human immunodeficiency virus. None of the compounds were active against the viruses nor were they cytotoxic at the highest concentration tested.