6-bromo-5-cyano-7-[(1,3-diacetoxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidin-4-one | 260352-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 6-bromo-5-cyano-7-[(1,3-diacetoxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidin-4-one
• 英文别名: [3-acetyloxy-2-[(6-bromo-5-cyano-4-oxo-1H-pyrrolo[2,3-d]pyrimidin-7-yl)methoxy]propyl] acetate
• CAS: 260352-88-3
• 化学式: C₁₅H₁₅BrN₄O₆
• 分子量: 427.211
• InChiKey: RKUDLNXSWYOEHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  132
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-bromo-5-cyano-7-[(1,3-diacetoxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidin-4-one 在 palladium on activated charcoal 盐酸 、 ammonium hydroxide 、 氨 、 氢气 、 三氯氧磷 作用下， 以 甲醇 、 乙醇 、 氯仿 、 乙酸乙酯 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 49.5h， 生成 6-amino-4-methyl-8-[(1,3-dihydroxy-2-propoxy)methyl]pyrrolo[4,3,2-de]pyrimido[4,5-c]pyridazine
  参考文献：
  名称：

  Acyclic Sugar Analogs of Triciribine: Lack of Antiviral and Antiproliferative Activity Correlate with Low Intracellular Phosphorylation

  摘要：

  Triciribine and triciribine monophosphate have antiviral and antiproliferative activity at low or submicromolar concentrations. In an effort to improve and better understand this activity, we have synthesized a series of acyclic analogs and evaluated them for activity against select viruses and cancer cell. lines. We conclude that the rigid ribosyl ring system of triciribine must be intact in order to be phosphorylated and to obtain significant antiviral and antiproliferative activity.

  DOI：

  10.1080/07328319908044621
• 作为产物：
  描述：

  4-amino-6-bromo-5-cyano-7-[(1,3-diacetoxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidine 在 溶剂黄146 、 sodium nitrite 、 水 、 碳酸氢钠 作用下， 以 水 为溶剂， 反应 18.5h， 以73%的产率得到6-bromo-5-cyano-7-[(1,3-diacetoxy-2-propoxy)methyl]pyrrolo[2,3-d]pyrimidin-4-one
  参考文献：
  名称：

  Acyclic Sugar Analogs of Triciribine: Lack of Antiviral and Antiproliferative Activity Correlate with Low Intracellular Phosphorylation

  摘要：

  Triciribine and triciribine monophosphate have antiviral and antiproliferative activity at low or submicromolar concentrations. In an effort to improve and better understand this activity, we have synthesized a series of acyclic analogs and evaluated them for activity against select viruses and cancer cell. lines. We conclude that the rigid ribosyl ring system of triciribine must be intact in order to be phosphorylated and to obtain significant antiviral and antiproliferative activity.

  DOI：

  10.1080/07328319908044621