(R)-β-[(2-propoxy-9-phenyl-1H-purin-6-yl)amino]benzenepropanol | 133973-93-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (R)-β-[(2-propoxy-9-phenyl-1H-purin-6-yl)amino]benzenepropanol
• 英文别名: (2R)-3-phenyl-2-[(9-phenyl-2-propoxypurin-6-yl)amino]propan-1-ol
• CAS: 133973-93-0
• 化学式: C₂₃H₂₅N₅O₂
• 分子量: 403.484
• InChiKey: NTRYVXHUXMWEIY-GOSISDBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  85.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (R)-β-[(2-propoxy-9-phenyl-1H-purin-6-yl)amino]benzenepropanol 在 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以8%的产率得到(R)-7,8-dihydro-3-phenyl-8-(phenylmethyl)-5-propoxy-3H-diimidazo[1,2-c:4',5'-e]pyrimidine
  参考文献：
  名称：

  Conformationally restrained, chiral (phenylisopropyl)amino-substituted pyrazolo[3,4-d]pyrimidines and purines with selectivity for adenosine A1 and A2 receptors

  摘要：

  Two modes of tethering a chiral (phenylisopropyl)amino substituent in pyrazolo[3,4-d]pyrimidines and purines have been explored. One mode gave (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-propoxy-3H-imidazo[1,2-c]pyrazolo-[4,3-e]pyrimidine (12a) and its corresponding R-enantiomer 12b, which were selective for A2 and A1 adenosine receptors, respectively. The corresponding diimidazo[1,2-c:4',5'-e]pyrimidines 12e and 12f were analogously selective. This is the first example where a single chiral recognition unit provides enantiomers with opposite selectivities for adenosine receptors. The second mode gave (2S-trans)-2,7-dihydro-2-methyl-3,7-diphenyl-5-propoxy-3H-imidazo[1,2-c]-pyrazolo[4,3-e]pyrimidine (12c) and its corresponding R-enantiomer 12d. Compounds 12c and 12d were significantly less potent than 12a and 12b at A1 receptors, and were nonselective.

  DOI：

  10.1021/jm00095a024
• 作为产物：
  描述：

  D-苯丙氨醇 在 三乙胺 作用下， 以 丙醇 、 乙醇 为溶剂， 反应 53.0h， 生成 (R)-β-[(2-propoxy-9-phenyl-1H-purin-6-yl)amino]benzenepropanol
  参考文献：
  名称：

  Conformationally restrained, chiral (phenylisopropyl)amino-substituted pyrazolo[3,4-d]pyrimidines and purines with selectivity for adenosine A1 and A2 receptors

  摘要：

  Two modes of tethering a chiral (phenylisopropyl)amino substituent in pyrazolo[3,4-d]pyrimidines and purines have been explored. One mode gave (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-propoxy-3H-imidazo[1,2-c]pyrazolo-[4,3-e]pyrimidine (12a) and its corresponding R-enantiomer 12b, which were selective for A2 and A1 adenosine receptors, respectively. The corresponding diimidazo[1,2-c:4',5'-e]pyrimidines 12e and 12f were analogously selective. This is the first example where a single chiral recognition unit provides enantiomers with opposite selectivities for adenosine receptors. The second mode gave (2S-trans)-2,7-dihydro-2-methyl-3,7-diphenyl-5-propoxy-3H-imidazo[1,2-c]-pyrazolo[4,3-e]pyrimidine (12c) and its corresponding R-enantiomer 12d. Compounds 12c and 12d were significantly less potent than 12a and 12b at A1 receptors, and were nonselective.

  DOI：

  10.1021/jm00095a024