2',3'-bis-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-N6-(endo-norborn-2-yl)adenosine | 910294-62-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 5'-脱氧核糖核苷
• 英文名称: 2',3'-bis-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-N6-(endo-norborn-2-yl)adenosine
• 英文别名: 2',3'-bis-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-N⁶-(endo-norborn-2-yl)adenosine；2',3'-bis-O-(tert-butyldimetylsilyl)-5'-chloro-5'-deoxy-N⁶-(endo-norborn-2-yl)adenosine
• CAS: 910294-62-1
• 化学式: C₂₉H₅₀ClN₅O₃Si₂
• 分子量: 608.372
• InChiKey: IYQYKJMFOVSJAS-YRUUFKTKSA-N

物化性质

• 沸点：
  639.5±65.0 °C(Predicted)
• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.34
• 重原子数：
  40.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  83.32
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2',3'-bis-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-N6-(endo-norborn-2-yl)adenosine 在 氟化铵 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 5'-deoxy-N⁶-(endo-norborn-2-yl)-5'-methylthioadenosine
  参考文献：
  名称：

  An expedient synthesis of N6-substituted-5′-modified adenosines

  摘要：

  Herein we report a short and efficient synthesis of N-6-substituted 5'-modified adenosines, which was achieved in four steps from 2',3,5'-tris-O-(tert-butyldimethylsilyl)inosine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.019
• 作为产物：
  描述：

  2',3',5'-tris-O-(tert-butyldimethylsilyl)inosine 在 氯化亚砜 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 叔丁醇 为溶剂， 反应 23.75h， 生成 2',3'-bis-O-(tert-butyldimethylsilyl)-5'-chloro-5'-deoxy-N6-(endo-norborn-2-yl)adenosine
  参考文献：
  名称：

  An expedient synthesis of N6-substituted-5′-modified adenosines

  摘要：

  Herein we report a short and efficient synthesis of N-6-substituted 5'-modified adenosines, which was achieved in four steps from 2',3,5'-tris-O-(tert-butyldimethylsilyl)inosine. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.06.019

文献信息

• Microwave-Assisted Direct Amination: Rapid Access to Multi-Functionalized N6-Substituted Adenosines
  作者：Trent D. Ashton、Peter J. Scammells

  DOI：10.1071/ch07340

  日期：——

  Analogues of adenosine have a range of interesting biological activities and potential therapeutic applications. A method for the efficient preparation of highly functionalized N6-substituted adenosines has been developed from the corresponding tert-butyldimethylsilyl-protected inosine. The key step in this procedure is a microwave-assisted amination reaction between an appropriately substituted inosine and an amine in the presence of PyBroP. High yields of desired N6-substituted adenosines were achieved with hindered amines and the reaction was also found to accommodate a range of substituents on the inosine precursor.

  腺苷的类似物具有一系列有趣的生物活性和潜在的治疗用途。从相应的叔丁基二甲基硅基保护肌苷出发，我们开发出了一种高效制备高官能度 N6 取代腺苷的方法。该方法的关键步骤是在 PyBroP 的存在下，在适当取代的肌苷和胺之间进行微波辅助胺化反应。使用受阻胺可以获得高产率的所需 N6 取代腺苷，而且该反应还能适应肌苷前体上的一系列取代基。
• N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists
  作者：T.D. Ashton、Stephen P. Baker、Sally A. Hutchinson、Peter J. Scammells

  DOI：10.1016/j.bmc.2007.11.010

  日期：2008.2.15

  Adenosines bearing 5'-modification in conjunction with an N-6-substituent have previously been shown to act as partial agonists at the A(1) adenosine receptor. Our current work investigates the effect of modifying the 5'-position in conjunction with efficacious bicyclic and tricyclic N-6-substituents. Several highly potent agonists for the A(1) adenosine receptor were identified; however, all of these compounds behaved as full agonists. In keeping with previous reports, 5'-halogen and 5'-sulfide derivatives of N-6-(endo-norborn-2-yl) adenosine were, in general, low nanomolar agonists of the A(1) adenosine receptor. The known partial agonist, N-6-cyclopentyl-5'-deoxy-5'-ethylthioadenosine (2), also behaved as a full agonist in our assay. (C) 2007 Elsevier Ltd. All rights reserved.