8-(1R,2S,4S)-1-Bicyclo[2.2.1]hept-2-ylmethyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione | 136199-04-7

• 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: 8-(1R,2S,4S)-1-Bicyclo[2.2.1]hept-2-ylmethyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
• 英文别名: 8-[[(1R,2S,4S)-2-bicyclo[2.2.1]heptanyl]methyl]-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 136199-04-7
• 化学式: C₁₉H₂₈N₄O₂
• 分子量: 344.457
• InChiKey: HQRJBFICGQWZHQ-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  N-(6-Amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-2-(1R,2S,4S)-bicyclo[2.2.1]hept-2-yl-acetamide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 8-(1R,2S,4S)-1-Bicyclo[2.2.1]hept-2-ylmethyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione
  参考文献：
  名称：

  8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors

  摘要：

  With the aim of characterizing the hydrophobic interactions between xanthines and the A1 receptor site, 1,3-dipropyl-8-substituted xanthines were synthesized. Introduction of a quaternary carbon and the conformationally restricted cyclopentyl moiety into the 8-position of xanthines enhanced the adenosine A1 antagonism. 1,3-Dipropyl-8-(3-noradamantyl)xanthine (42) was identified to be a selective and the most potent A1 receptor antagonist reported to date. Under our structure-activity relationship, the 8-substituent of xanthine antagonists and the N6-substituent of adenosine agonists appears to bind to the same region of the A1 receptor.

  DOI：

  10.1021/jm00083a018