8-cyano-3',5'-di-O-acetyl-2'-deoxyadenosine | 1058641-26-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 8-cyano-3',5'-di-O-acetyl-2'-deoxyadenosine
• CAS: 1058641-26-1
• 化学式: C₁₅H₁₆N₆O₅
• 分子量: 360.329
• InChiKey: BPUYAUMSWKXTCJ-HOSYDEDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.06
• 重原子数：
  26.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  155.24
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  8-cyano-3',5'-di-O-acetyl-2'-deoxyadenosine 在 sodium hydroxide 、 水 作用下， 反应 12.0h， 以55%的产率得到6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purine-8-carboxamide
  参考文献：
  名称：

  Synthesis and Primary Evaluation of Novel HIV-1 Inhibitors

  摘要：

  The overcoming of antiviral drug resistance is an important challenge in the treatment of HIV-1 infection.According to the theory of viral error catastrophe, slightly increasing the mutation rate could exceed the error threshold for viability of a viral population and kill it. Investigation of this mechanism could lead to the discovery of new antiviral agents capable of bypassing viral resistance.To this aim, we designed several modified nucleosides. We describe here the synthesis and partial evaluation of 8-amido-2'-deoxyadenosine. The supplementary amide group on the base should allow base-pairing with several natural nucleosides, thus creating supplementary mutations that would kill the virus.

  DOI：

  10.1080/15257770701527109
• 作为产物：
  描述：

  8-(methylsulfonyl)-3',5'-di-O-acetyl-2'-deoxyadenosine 、 氰化钠 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以95%的产率得到8-cyano-3',5'-di-O-acetyl-2'-deoxyadenosine
  参考文献：
  名称：

  Synthesis and Primary Evaluation of Novel HIV-1 Inhibitors

  摘要：

  The overcoming of antiviral drug resistance is an important challenge in the treatment of HIV-1 infection.According to the theory of viral error catastrophe, slightly increasing the mutation rate could exceed the error threshold for viability of a viral population and kill it. Investigation of this mechanism could lead to the discovery of new antiviral agents capable of bypassing viral resistance.To this aim, we designed several modified nucleosides. We describe here the synthesis and partial evaluation of 8-amido-2'-deoxyadenosine. The supplementary amide group on the base should allow base-pairing with several natural nucleosides, thus creating supplementary mutations that would kill the virus.

  DOI：

  10.1080/15257770701527109