(2R,3R,4R,5S)-4-azido-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol | 197796-86-4

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: (2R,3R,4R,5S)-4-azido-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol
• CAS: 197796-86-4
• 化学式: C₁₅H₂₀N₈O₃
• 分子量: 360.376
• InChiKey: NIBISTMBSRBOAU-KVQFHVITSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  120
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (2R,3R,4R,5S)-4-azido-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 4-Amino-2-(6-cyclopentylamino-purin-9-yl)-5-hydroxymethyl-tetrahydro-furan-3-ol
  参考文献：
  名称：

  3′-Amidated 3′-Deoxyxylofuranose Analogues of N ⁶-⁻Cyclopentyladenosines: a New Class of Non-Xanthine Antagonists at the Adenosine A₁ Receptor.

  摘要：

  Full adenosine A(1) receptor agonists like CPA and other N-6-substituted adenosine analogs have previously been shown to become partial agonists upon deletion of the 3'-hydroxyl moiety. The present study further explored the C-3' site for modification. The modest affinity at A(1) and A(2a) receptors found in the 3'-amido-3'-deoxyxylofuranosyladenine series prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to exhibit potent antagonistic behaviour at the A(1) receptors. This represents a new perspective in the purinergic field.

  DOI：

  10.1080/07328319808004688
• 作为产物：
  描述：

  N6-环戊基腺苷酸 在 sodium azide 、 2-乙酰氧基异丁酰溴 、 水 、 sodium methylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (2R,3R,4R,5S)-4-azido-2-[6-(cyclopentylamino)purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  3′-Amidated 3′-Deoxyxylofuranose Analogues of N ⁶-⁻Cyclopentyladenosines: a New Class of Non-Xanthine Antagonists at the Adenosine A₁ Receptor.

  摘要：

  Full adenosine A(1) receptor agonists like CPA and other N-6-substituted adenosine analogs have previously been shown to become partial agonists upon deletion of the 3'-hydroxyl moiety. The present study further explored the C-3' site for modification. The modest affinity at A(1) and A(2a) receptors found in the 3'-amido-3'-deoxyxylofuranosyladenine series prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to exhibit potent antagonistic behaviour at the A(1) receptors. This represents a new perspective in the purinergic field.

  DOI：

  10.1080/07328319808004688

文献信息

• <i>N</i>⁶-Cyclopentyl-3‘-substituted-xylofuranosyladenosines:  A New Class of Non-Xanthine Adenosine A₁ Receptor Antagonists
  作者：Serge Van Calenbergh、Jacobien K. von Frijtag Drabbe Künzel、Norbert M. Blaton、Oswald M. Peeters、Jef Rozenski、Arthur Van Aerschot、Andre De Bruyn、Denis De Keukeleire、Adriaan P. IJzerman、Piet Herdewijn

  DOI：10.1021/jm970176k

  日期：1997.11.1

  The present study explores the C-3' site of the 3-deoxy-3-xylofuranosyl ring of nucleoside analogues with an adenine or N-6-cyclopentyladenine (CPA) base moiety and evaluates the effect on adenosine receptor affinity. Two series of sugar-modified adenosines, i.e., 3'-amido-3'-deoxyadenosines and 3'-amidated 3'-deoxyxylofuranosyladenines, were synthesized and tested for their affinity at A(1) and A(2a) receptors in rat brain cortex and rat striatum, respectively. The modest affinity found in the ''xylo series'' prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to be well accommodated by the A(1) receptors with potencies in the lower nanomolar range. This represents a new perspective in the purinergic field. The absence of a GTP-induced shift, i.e., the ratio between the affinities measured in the presence and absence of 1 mM GTP indicates an antagonistic behavior of this new class of CPA analogues.
• 3′-Amidated 3′-Deoxyxylofuranose Analogues of <i>N</i> ⁶-⁻Cyclopentyladenosines: a New Class of Non-Xanthine Antagonists at the Adenosine A₁ Receptor.
  作者：Serge Van Calenbergh、Adriaan P. IJzerman、Piet Herdewijn

  DOI：10.1080/07328319808004688

  日期：1998.9

  Full adenosine A(1) receptor agonists like CPA and other N-6-substituted adenosine analogs have previously been shown to become partial agonists upon deletion of the 3'-hydroxyl moiety. The present study further explored the C-3' site for modification. The modest affinity at A(1) and A(2a) receptors found in the 3'-amido-3'-deoxyxylofuranosyladenine series prompted us to synthesize the corresponding N-6-cyclopentyl derivatives, which proved to exhibit potent antagonistic behaviour at the A(1) receptors. This represents a new perspective in the purinergic field.