9-[(E)-2-fluoro-4-hydroxy-3-methyl-but-2-enyl]-2-amino-6-oxo-1H-purine | 1093449-54-7

• 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-[(E)-2-fluoro-4-hydroxy-3-methyl-but-2-enyl]-2-amino-6-oxo-1H-purine
• 英文别名: 2-amino-9-[(E)-2-fluoro-4-hydroxy-3-methylbut-2-enyl]-1H-purin-6-one
• CAS: 1093449-54-7
• 化学式: C₁₀H₁₂FN₅O₂
• 分子量: 253.236
• InChiKey: GAVRVAOJCLPGIT-AATRIKPKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  9-[(E)-2-fluoro-4-hydroxy-3-methyl-but-2-enyl]-2-amino-6-chloro-purine 在 sodium methylate 、 2-巯基乙醇 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.0h， 以67%的产率得到9-[(E)-2-fluoro-4-hydroxy-3-methyl-but-2-enyl]-2-amino-6-oxo-1H-purine
  参考文献：
  名称：

  Selective Synthesis and Application to the Synthesis of (E)-Fluorovinyl Nucleosides

  摘要：

  A selective method for synthesizing (E)fluorovinyl was developed. Novel acyclic (E)-fluorovinyl versions of neplanocin A were designed and selectively synthesized as potential antiviral agents. The condensation of the bromide 7 with the nucleosidic bases (5-FU, C, A, G) and the deprotection afforded the desired acyclic fluorovinyl nucleosides. The synthesized compounds 11, 12, 13, and 16 were evaluated for their antiviral activity. The guanine derivative 16 showed toxicity-dependent anti-HIV-1 activity in MT-4 cells.

  DOI：

  10.1080/15257770701845170

文献信息

• Selective Synthesis and Application to the Synthesis of (<i>E</i>)-Fluorovinyl Nucleosides
  作者：Qingbo Shen、Joon Hee Hong

  DOI：10.1080/15257770701845170

  日期：2008.2.8

  A selective method for synthesizing (E)fluorovinyl was developed. Novel acyclic (E)-fluorovinyl versions of neplanocin A were designed and selectively synthesized as potential antiviral agents. The condensation of the bromide 7 with the nucleosidic bases (5-FU, C, A, G) and the deprotection afforded the desired acyclic fluorovinyl nucleosides. The synthesized compounds 11, 12, 13, and 16 were evaluated for their antiviral activity. The guanine derivative 16 showed toxicity-dependent anti-HIV-1 activity in MT-4 cells.