8-(2-exo-norbornen-5-yl)-1,3-dipropylxanthine | 133058-80-7

• 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-(2-exo-norbornen-5-yl)-1,3-dipropylxanthine
• 英文别名: 8-[(1S,2R,4S)-2-bicyclo[2.2.1]hept-5-enyl]-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 133058-80-7；136198-90-8；136198-91-9
• 化学式: C₁₈H₂₄N₄O₂
• 分子量: 328.414
• InChiKey: LMZOGRHOEMOQIR-YNEHKIRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.39
• 重原子数：
  24.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  72.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  5-降冰片烯-2-羧酸 在 盐酸 、 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.17h， 生成 8-(2-exo-norbornen-5-yl)-1,3-dipropylxanthine
  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