-α-<1-<(1-phenyl-6-propoxy-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>ethyl>benzenemethanol

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: -α-<1-<(1-phenyl-6-propoxy-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>ethyl>benzenemethanol
• 英文别名: (S-(R*,S*))-α-{1-[(1-phenyl-6-propoxy-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]ethyl}benzenemethanol；(1R,2S)-1-phenyl-2-[(1-phenyl-6-propoxypyrazolo[3,4-d]pyrimidin-4-yl)amino]propan-1-ol
• 化学式: C₂₃H₂₅N₅O₂
• 分子量: 403.484
• InChiKey: IEVBPGAANNEBGZ-JXFKEZNVSA-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：
  8
• 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

• 作为产物：
  描述：

  去甲麻黄碱 以 丙醇 、 乙醇 为溶剂， 反应 72.0h， 生成 -α-<1-<(1-phenyl-6-propoxy-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>ethyl>benzenemethanol
  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