(R)-N-(1-methyl-2-phenylethyl)-9H-purin-6-amine | 30302-57-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (R)-N-(1-methyl-2-phenylethyl)-9H-purin-6-amine
• 英文别名: (1-Methyl-2-phenyl-ethyl)-(9H-purin-6-yl)-amine；N-[(2R)-1-phenylpropan-2-yl]-7H-purin-6-amine
• CAS: 30302-57-9
• 化学式: C₁₄H₁₅N₅
• 分子量: 253.307
• InChiKey: PWRQUKLRIZMCIA-SNVBAGLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-N-(1-methyl-2-phenylethyl)-9H-purin-6-amine 在 硫酸氢铵 、 ammonium hydroxide 、 TMSTf 作用下， 以 甲醇 、 1,2-二氯乙烷 为溶剂， 反应 22.0h， 生成 (R)-9-α-L-lyxopyranosyl-N-(1-methyl-2-phenylethyl)-9H-purin-6-amine
  参考文献：
  名称：

  Ribose-modified adenosine analogs as adenosine receptor agonists

  摘要：

  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.

  DOI：

  10.1021/jm00153a008
• 作为产物：
  描述：

  左苯丙胺 、 6-氯嘌呤 以 乙醇 为溶剂， 反应 72.0h， 以87%的产率得到(R)-N-(1-methyl-2-phenylethyl)-9H-purin-6-amine
  参考文献：
  名称：

  Ribose-modified adenosine analogs as adenosine receptor agonists

  摘要：

  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.

  DOI：

  10.1021/jm00153a008