5'-amino-2',3'-bis-O-(tert-butyldimetylsilyl)-5'-deoxy-N⁶-(endo-norborn-2-yl)adenosine | 910294-64-3

• 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: 5'-amino-2',3'-bis-O-(tert-butyldimetylsilyl)-5'-deoxy-N⁶-(endo-norborn-2-yl)adenosine
• CAS: 910294-64-3
• 化学式: C₂₉H₅₂N₆O₃Si₂
• 分子量: 588.941
• InChiKey: DSTQNLIDTMMDSK-YRUUFKTKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.06
• 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：
  109.34
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5'-amino-2',3'-bis-O-(tert-butyldimetylsilyl)-5'-deoxy-N⁶-(endo-norborn-2-yl)adenosine 在 氟化铵 作用下， 以 甲醇 为溶剂， 以60.6%的产率得到5'-amino-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
• 作为产物：
  描述：

  5'-azido-2',3'-bis-O-(tert-butyldimetylsilyl)-5'-deoxy-N6-(endo-norborn-2-yl)adenosine 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以89.1%的产率得到5'-amino-2',3'-bis-O-(tert-butyldimetylsilyl)-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

• 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.