9-(4'-acetoxy-5'-fluoropentyl)-2-amino-6-chloro-9H-purine | 153780-79-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-(4'-acetoxy-5'-fluoropentyl)-2-amino-6-chloro-9H-purine
• 英文别名: [5-(2-amino-6-chloropurin-9-yl)-1-fluoropentan-2-yl] acetate
• CAS: 153780-79-1
• 化学式: C₁₂H₁₅ClFN₅O₂
• 分子量: 315.735
• InChiKey: SQLNMAOQDVLCKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  95.92
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  9-(4'-acetoxy-5'-fluoropentyl)-2-amino-6-chloro-9H-purine 在 盐酸 作用下， 反应 2.0h， 以83%的产率得到9-(5'-fluoro-4'-hydroxypentyl)-9H-guanine
  参考文献：
  名称：

  Fluorinated Carbaacyclonucleosides: Synthesis and Evaluation of Antiviral Activity

  摘要：

  Two series of fluoroacyclic nucleosides were synthesised by condensation of nucleic acid bases with substituted fluoropentanes. 1-(5'-Fluoro-4'-hydroxypentyl)-cytosine showed a modest activity against cytomegalovirus (MIC(50): 12-15 mu g/ml). All the other compounds were inactive against all the viruses tested.

  DOI：

  10.1080/15257779508010714
• 作为产物：
  描述：

  2-(fluoromethyl)tetrahydrofuran 在 potassium carbonate 、 sodium iodide 作用下， 以 二甲基亚砜 、 乙腈 为溶剂， 反应 70.0h， 生成 9-(4'-acetoxy-5'-fluoropentyl)-2-amino-6-chloro-9H-purine
  参考文献：
  名称：

  9-(1-Fluoro-5-hydroxypentan-2-yl)-9H-guanine: synthesis and evaluation of antiviral activity

  摘要：

  5-Fluoro-4-tosyloxypentyl pivalate has been synthesized in four steps from 2-(fluoromethyl)tetrahydrofuran. Condensation with 2-amino-6-chloropurine gave the N-9 derivative, which was converted via the 6-methoxy analogue into 9-(1-fluoro-5-hydroxypentan-2-yl)-9H-guanine. The latter was evaluated, and found inactive, in a large variety of antiviral assays.

  DOI：

  10.1039/p19930002107