8-bromo-9-isopropyl-9H-adenine | 1152568-07-4

• 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: 8-bromo-9-isopropyl-9H-adenine
• 英文别名: 8-bromo-9-propan-2-ylpurin-6-amine
• CAS: 1152568-07-4
• 化学式: C₈H₁₀BrN₅
• 分子量: 256.105
• InChiKey: AFKIJCJUVRTHPD-UHFFFAOYSA-N

物化性质

• 熔点：
  198-200 °C
• 沸点：
  424.8±48.0 °C(predicted)
• 密度：
  1.87±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  69.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-bromo-9-isopropyl-9H-adenine 在 四(三苯基膦)钯 、 sodium carbonate 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.83h， 生成 5-(6-amino-9-isopropyl-9H-purin-8-yl)-2-fluorophenyl pent-4-ynoate
  参考文献：
  名称：

  Development of a cell-permeable adenine-derived probe for capture of nucleotide-binding proteins in living cells

  摘要：

  DOI：

  10.1016/j.cclet.2023.108455
• 作为产物：
  描述：

  9-isopropyladenine 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 103.0h， 以40%的产率得到8-bromo-9-isopropyl-9H-adenine
  参考文献：
  名称：

  8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands

  摘要：

  Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radioligand binding assays or functional cyclase experiments in respect to their interaction with all the four adenosine receptor subtypes. Results show that the presence of the bromine atom in 8-position of 9-substituted adenines promotes in general the interaction with the adenosine receptors, in particular at the A(2A) subtype. The present study also demonstrates that adenine derivatives could be a good starting point to obtain selective adenosine A(2B) receptor antagonists. (c) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.02.030

文献信息

• 8-Bromo-9-alkyl adenine derivatives as tools for developing new adenosine A2A and A2B receptors ligands
  作者：Catia Lambertucci、Ippolito Antonini、Michela Buccioni、Diego Dal Ben、Dhuldeo D. Kachare、Rosaria Volpini、Karl-Norbert Klotz、Gloria Cristalli

  DOI：10.1016/j.bmc.2009.02.030

  日期：2009.4

  Importance of making available selective adenosine receptor antagonists is boosted by recent findings of adenosine involvement in many CNS dysfunctions. In the present work a series of 8-bromo-9-alkyl adenines are prepared and fully characterized in radioligand binding assays or functional cyclase experiments in respect to their interaction with all the four adenosine receptor subtypes. Results show that the presence of the bromine atom in 8-position of 9-substituted adenines promotes in general the interaction with the adenosine receptors, in particular at the A(2A) subtype. The present study also demonstrates that adenine derivatives could be a good starting point to obtain selective adenosine A(2B) receptor antagonists. (c) 2009 Elsevier Ltd. All rights reserved.
• Development of a cell-permeable adenine-derived probe for capture of nucleotide-binding proteins in living cells
  作者：Lihong Liu、Rui Chen、Gang Xue、Chenzhou Hao、Weizhi Weng、Zhengying Pan

  DOI：10.1016/j.cclet.2023.108455

  日期：2024.3