2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-N-[(1,12-dicarba-closo-dodecaboran-1-yl)propan-3-yl]adenosine | 1417822-31-1

• 英文名称: 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-N-[(1,12-dicarba-closo-dodecaboran-1-yl)propan-3-yl]adenosine
• CAS: 1417822-31-1
• 化学式: C₃₃H₇₁B₁₀N₅O₄Si₃
• 分子量: 794.324
• InChiKey: XFGRLDKCQHLWKN-ZYWWQZICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-N-[(1,12-dicarba-closo-dodecaboran-1-yl)propan-3-yl]adenosine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以78%的产率得到6-N-[(1,12-dicarba-closo-dodecaboran-1-yl)propan-3-yl]adenosine
  参考文献：
  名称：

  Effect of adenosine modified with a boron cluster pharmacophore on reactive oxygen species production by human neutrophils

  摘要：

  Methods for the synthesis of adenosine/boron cluster conjugates are proposed and the potential of the obtained derivatives to modulate neutrophil activity, especially reactive oxygen species (ROS) production in vitro, is described. An efficient inhibition of ROS production in activated neutrophils by adenosine modified at the 2'-C and 6-N positions with a para-carborane cluster (C2B10H11) was discovered. The high affinity of the selected compounds for adenosine receptor A(2A) was established. These results are in agreement with the possible involvement of receptor A(2A) in the biological activities of adenosine/boron cluster conjugates. This study extends the range of innovative molecules available for testing as agents affecting inflammatory processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.039
• 作为产物：
  描述：

  腺苷 在 咪唑 、 四氯化碳 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 32.0h， 生成 2',3',5'-tri-O-(tert-butyldimethylsilyl)-6-N-[(1,12-dicarba-closo-dodecaboran-1-yl)propan-3-yl]adenosine
  参考文献：
  名称：

  Effect of adenosine modified with a boron cluster pharmacophore on reactive oxygen species production by human neutrophils

  摘要：

  Methods for the synthesis of adenosine/boron cluster conjugates are proposed and the potential of the obtained derivatives to modulate neutrophil activity, especially reactive oxygen species (ROS) production in vitro, is described. An efficient inhibition of ROS production in activated neutrophils by adenosine modified at the 2'-C and 6-N positions with a para-carborane cluster (C2B10H11) was discovered. The high affinity of the selected compounds for adenosine receptor A(2A) was established. These results are in agreement with the possible involvement of receptor A(2A) in the biological activities of adenosine/boron cluster conjugates. This study extends the range of innovative molecules available for testing as agents affecting inflammatory processes. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.039