(S)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol | 132537-82-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (S)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol
• 英文别名: (S)-β-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol；(S)-beta-[(1-phenyl-6-chloro-1H-pyrazolo[3,4-d]pyrimidin-4-yl)amino]benzenepropanol；(2S)-2-[(6-chloro-1-phenylpyrazolo[3,4-d]pyrimidin-4-yl)amino]-3-phenylpropan-1-ol
• CAS: 132537-82-7
• 化学式: C₂₀H₁₈ClN₅O
• 分子量: 379.849
• InChiKey: BWBZMISJGXVMIQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  75.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol 在 氯化亚砜 作用下， 以 丙醇 、 氯仿 为溶剂， 反应 1.0h， 生成 (S)-2,7-dihydro-7-phenyl-2-(phenylmethyl)-5-propoxy-3H-imidazo[1,2-c]pyrazolo[4,3-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：

  L-苯丙氨醇 、 4,6-二氯-1-苯基-1氢-吡唑[3,4-d]并嘧啶 以 乙醇 为溶剂， 以97%的产率得到(S)-β-<(1-phenyl-6-chloro-1H-pyrazolo<3,4-d>pyrimidin-4-yl)amino>benzenepropanol
  参考文献：
  名称：

  Selective adenosine reseptor compounds

  摘要：

  本文披露了具有选择性作用于腺苷受体并通常作为腺苷拮抗剂的腺苷类似物。从体外研究中已知，由于这种选择性，可以区分出特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。基于本文所披露的化合物的选择性结合活性，可以制备药物制剂，预计可以增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。

  公开号：

  US05064947A1

文献信息

• Tricyclic fused adenine derivatives
  申请人：Merrell Dow Pharmaceuticals Inc.

  公开号：US05086176A1

  公开（公告）日：1992-02-04

  Adenosine analogues which act selectively at adenosine receptors and which act in general as adenosine antagonists are disclosed. From in vitro studies it is known that specific physiological effects can be distinguished as a result of this selectivity and that adenosine receptor activity in vitro correlates with adenosine receptor activity in vivo. Pharmaceutical preparations of the subject compounds can be prepared on the basis of the selective binding activity of the compounds disclosed herein which can be expected to enhance certain physiological effects while minimizing others, such as decreasing blood pressure without decreasing heart rate.

  本文披露了选择性作用于腺苷受体并且通常作为腺苷拮抗剂的腺苷类似物。从体外研究中已知，由于这种选择性，可以区分特定的生理效应，并且体外腺苷受体活性与体内腺苷受体活性相关。基于本文中披露的化合物的选择性结合活性，可以制备主题化合物的制药制剂，可以预期增强某些生理效应，同时最小化其他效应，例如降低血压而不降低心率。
• Selective adenosine receptor agents
  申请人：MERRELL PHARMACEUTICALS INC.

  公开号：EP0390112B1

  公开（公告）日：1998-01-28
• Selective adenosine receptor compounds
  申请人：MERRELL DOW PHARMACEUTICALS INC.

  公开号：EP0390111B1

  公开（公告）日：1994-09-14
• US5064947A
  申请人：——

  公开号：US5064947A

  公开（公告）日：1991-11-12
• US5086176A
  申请人：——

  公开号：US5086176A

  公开（公告）日：1992-02-04