N6-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine | 1020103-13-2

• 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: N6-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine
• 英文别名: N⁶-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine
• CAS: 1020103-13-2
• 化学式: C₂₉H₅₃N₅O₃SSi₂
• 分子量: 608.009
• InChiKey: OPEQPVPYGQGNNT-VBHAUSMQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.61
• 重原子数：
  40.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• 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：
  9.0

反应信息

• 作为反应物：
  描述：

  N6-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine 在 氟化铵 作用下， 以 甲醇 为溶剂， 以37%的产率得到N⁶-cyclopentyl-5'-deoxy-5'-ethylthioadenosine
  参考文献：
  名称：

  N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.11.010
• 作为产物：
  描述：

  2',3'-bis-O-(tert-butyldimetylsilyl)-5'-chloro-5'-deoxyinosine 、 环戊胺 在 N,N-二异丙基乙胺 、 bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 22.0h， 以91.6%的产率得到N6-cyclopentyl-2',3'-bis-O-(tert-butyldimethylsilyl)-5'-deoxy-5'-ethylthioadenosine
  参考文献：
  名称：

  N6-substituted C5′-modified adenosines as A1 adenosine receptor agonists

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.11.010