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

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-6-(trifluoromethyl)-9H-purine
• 英文别名: 9-[(1R,2R,4S)-2-bicyclo[2.2.1]heptanyl]-6-(trifluoromethyl)purine
• 化学式: C₁₃H₁₃F₃N₄
• 分子量: 282.268
• InChiKey: TZMWHUGCMMKFPC-DJLDLDEBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (三氟甲基)三甲基硅烷 、 9-[(1RS,2RS,4SR)-bicyclo[2.2.1]hept-2-yl]-6-chloro-9H-purine 在 potassium fluoride 、 copper(l) iodide 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.0h， 以81%的产率得到9-[(1R*,2R*,4S*)-bicyclo[2.2.1]hept-2-yl]-6-(trifluoromethyl)-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

文献信息

• SAR studies of 9-norbornylpurines as Coxsackievirus B3 inhibitors
  作者：Michal Šála、Armando M. De Palma、Hubert Hřebabecký、Milan Dejmek、Martin Dračínský、Pieter Leyssen、Johan Neyts、Helena Mertlíková-Kaiserová、Radim Nencka

  DOI：10.1016/j.bmcl.2011.05.070

  日期：2011.7

  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.