5-[1-(t-hydroxymethyl)cyclobutylmethyl]isocytosine | 1234357-68-6

• 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-[1-(t-hydroxymethyl)cyclobutylmethyl]isocytosine
• 英文别名: 2-amino-5-[[1-(hydroxymethyl)cyclobutyl]methyl]-1H-pyrimidin-4-one；2-amino-5-[[1-(hydroxymethyl)cyclobutyl]methyl]-1H-pyrimidin-6-one
• CAS: 1234357-68-6
• 化学式: C₁₀H₁₅N₃O₂
• 分子量: 209.248
• InChiKey: UVQJMOQJWDNJDB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  87.7
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-[1-(t-hydroxymethyl)cyclobutylmethyl]isocytosine 在 四氮唑 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-(isocytosine-5-ylmethyl)-cyclobutulmethyl bis(pivaloyl-2-thioethyl) phosphate
  参考文献：
  名称：

  Design and Synthesis of Novel Sate Derivatives of Acyclic Isocytosine and 9-DeazaadenineC-Nucleosides

  摘要：

  This article describes a very simple route for synthesizing novel lipophilic phosphate bis(t-bu-SATE) prodrugs of acyclic cyclobutylated C-nucleosides such as isocytosine 12 and 9-deazaadenine 19, which were prepared from 1,1-gem cyclobutyl dicarboxylate. Synthesized compounds were evaluated as potential antiviral agents against HIV virus. Some phosphate SATE prodrugs were more active against HIV than parent nucleosides.

  DOI：

  10.1080/15257771003745704
• 作为产物：
  描述：

  5-[1-(t-butyldimethylsilanyloxymethyl)cyclobutylmethyl]isocytosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 以79%的产率得到5-[1-(t-hydroxymethyl)cyclobutylmethyl]isocytosine
  参考文献：
  名称：

  Design and Synthesis of Novel Sate Derivatives of Acyclic Isocytosine and 9-DeazaadenineC-Nucleosides

  摘要：

  This article describes a very simple route for synthesizing novel lipophilic phosphate bis(t-bu-SATE) prodrugs of acyclic cyclobutylated C-nucleosides such as isocytosine 12 and 9-deazaadenine 19, which were prepared from 1,1-gem cyclobutyl dicarboxylate. Synthesized compounds were evaluated as potential antiviral agents against HIV virus. Some phosphate SATE prodrugs were more active against HIV than parent nucleosides.

  DOI：

  10.1080/15257771003745704

文献信息

• Design and Synthesis of Novel Sate Derivatives of Acyclic Isocytosine and 9-Deazaadenine<i>C</i>-Nucleosides
  作者：Lian Jin Liu、Joon Hee Hong

  DOI：10.1080/15257771003745704

  日期：2010.4.20

  This article describes a very simple route for synthesizing novel lipophilic phosphate bis(t-bu-SATE) prodrugs of acyclic cyclobutylated C-nucleosides such as isocytosine 12 and 9-deazaadenine 19, which were prepared from 1,1-gem cyclobutyl dicarboxylate. Synthesized compounds were evaluated as potential antiviral agents against HIV virus. Some phosphate SATE prodrugs were more active against HIV than parent nucleosides.