3'-deoxy-N⁶(R)-(phenylisopropyl)adenosine

• 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: 3'-deoxy-N⁶(R)-(phenylisopropyl)adenosine
• 英文别名: (R)-3'-deoxy-N-(1-methyl-2-phenylethyl)adenosine；(2R,3R,5S)-5-(hydroxymethyl)-2-[6-[[(2R)-1-phenylpropan-2-yl]amino]purin-9-yl]oxolan-3-ol
• 化学式: C₁₉H₂₃N₅O₃
• 分子量: 369.423
• InChiKey: BFXHWITVJAUCOT-NMLBAAHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  虫草素 在 吡啶 、 4-二甲氨基吡啶 、 二碘甲烷 、 亚硝酸异戊酯 作用下， 以 乙醇 为溶剂， 反应 366.0h， 生成 3'-deoxy-N⁶(R)-(phenylisopropyl)adenosine
  参考文献：
  名称：

  Ribose-Modified Adenosine Analogs as Potential Partial Agonists for the Adenosine Receptor

  摘要：

  We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N-6-substituted adenosines: protection of the hydroxyl groups, replacement of the N-6-amino by a better leaving group, and combined deprotection and N-6-amination in the last step. This route was used to synthesize deoxy analogues of CPA, CHA, and R- and S-PIA. The compounds were tested on the adenosine A(1) and A(2a) receptors in our search for partial agonists for these receptors. The GTP shift was used as an in vitro measure for the intrinsic activity of these compounds; the in vivo intrinsic activities of the deoxy analogues of CPA and R-PIA were determined in the rat cardiovascular system. Thus, it was shown that the hydroxyl groups are determinants for the affinity and intrinsic activity of these analogues. Removal of the 2'-and 3'-hydroxyl groups affects affinity and intrinsic activity, whereas removal of the 5'-hydroxyl group decreases only affinity.

  DOI：

  10.1021/jm00020a014

文献信息

• Ribose-modified adenosine analogs as adenosine receptor agonists
  作者：Michael D. Taylor、Walter H. Moos、Harriet W. Hamilton、Deedee S. Szotek、William C. Patt、Edward W. Badger、James A. Bristol、Robert F. Bruns、Thomas G. Heffner、Thomas E. Mertz

  DOI：10.1021/jm00153a008

  日期：1986.3

  Analogues of the potent adenosine receptor agonist (R)-N-(1-methyl-2-phenylethyl)adenosine (R-PIA), modified at N9, were prepared and evaluated for adenosine A1 and A2 receptor binding and in vivo central nervous system and cardiovascular effects. The modifications at N9 include deoxy sugars, 5'-substituted-5'-deoxyriboses, non-ribose sugars, sugar ring homologues, and acyclic sugar analogues. Most of the derivatives have poor affinity for adenosine receptors. Only minor modifications at C5' and C3' maintain potent binding. In general, those derivatives exhibiting in vivo behavioral or cardiovascular effects also have the highest affinity for adenosine receptors.
• Ribose-Modified Adenosine Analogs as Potential Partial Agonists for the Adenosine Receptor
  作者：Eleonora M. van der Wenden、Jacobien K. von Frijtag Drabbe Kuenzel、Ron A. A. Mathot、Meindert Danhof、Adriaan P. IJzerman、Willem Soudijn

  DOI：10.1021/jm00020a014

  日期：1995.9

  We have adopted a practical three-step route for the synthesis of 2'- and 3'-deoxy analogues of N-6-substituted adenosines: protection of the hydroxyl groups, replacement of the N-6-amino by a better leaving group, and combined deprotection and N-6-amination in the last step. This route was used to synthesize deoxy analogues of CPA, CHA, and R- and S-PIA. The compounds were tested on the adenosine A(1) and A(2a) receptors in our search for partial agonists for these receptors. The GTP shift was used as an in vitro measure for the intrinsic activity of these compounds; the in vivo intrinsic activities of the deoxy analogues of CPA and R-PIA were determined in the rat cardiovascular system. Thus, it was shown that the hydroxyl groups are determinants for the affinity and intrinsic activity of these analogues. Removal of the 2'-and 3'-hydroxyl groups affects affinity and intrinsic activity, whereas removal of the 5'-hydroxyl group decreases only affinity.