9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-8-methoxy-9H-purine-6-amine

• 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-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-8-methoxy-9H-purine-6-amine
• 英文别名: 9-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]-8-methoxypurin-6-amine
• 化学式: C₁₃H₁₇N₅O
• 分子量: 259.311
• InChiKey: AKNGJXPKQDVJSH-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-8-methoxy-9H-purine-6-amine 在 四氯化碳 、 亚硝酸异戊酯 作用下， 以44%的产率得到9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-6-chloro-8-methoxy-9H-purine
  参考文献：
  名称：

  SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors

  摘要：

  Coxsackievirus and related enteroviruses are important human pathogens that cause various diseases with clinical manifestations ranging from trivial flu-like syndromes to dangerous or even fatal diseases such as myocarditis, meningitis and encephalitis. Here, we report on our continuous SAR study focused on 9-(bicyclo[2.2.1] hept-2-yl)-9H-purines as anti-enteroviral inhibitors. The purine moiety was modified at positions 2, 6 and 8. Several analogues inhibited Coxsackievirus B3 as well as other enteroviruses at low-micromolar concentrations. The 6-chloropurine derivative was confirmed as the most active compound in this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.070
• 作为产物：
  描述：

  8-溴腺嘌呤 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 96.0h， 生成 9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-8-methoxy-9H-purine-6-amine
  参考文献：
  名称：

  SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors

  摘要：

  Coxsackievirus and related enteroviruses are important human pathogens that cause various diseases with clinical manifestations ranging from trivial flu-like syndromes to dangerous or even fatal diseases such as myocarditis, meningitis and encephalitis. Here, we report on our continuous SAR study focused on 9-(bicyclo[2.2.1] hept-2-yl)-9H-purines as anti-enteroviral inhibitors. The purine moiety was modified at positions 2, 6 and 8. Several analogues inhibited Coxsackievirus B3 as well as other enteroviruses at low-micromolar concentrations. The 6-chloropurine derivative was confirmed as the most active compound in this series. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.05.070