6-amino-1,3-dipropyl-5-<<(2,2,5,5-tetramethylcyclopentyl)carbonyl>amino>uracil | 139348-58-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-amino-1,3-dipropyl-5-<<(2,2,5,5-tetramethylcyclopentyl)carbonyl>amino>uracil
• 英文别名: N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)-2,2,5,5-tetramethylcyclopentane-1-carboxamide
• CAS: 139348-58-6
• 化学式: C₂₀H₃₄N₄O₃
• 分子量: 378.515
• InChiKey: MZXZUNFTSSFJBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  95.7
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-amino-1,3-dipropyl-5-<<(2,2,5,5-tetramethylcyclopentyl)carbonyl>amino>uracil 在 三氯氧磷 作用下， 反应 1.5h， 生成 1,3-dipropyl-8-(2,2,5,5-tetramethylcyclopentyl)xanthine
  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
• 作为产物：
  描述：

  2,2,5,5-Tetramethylcyclopentanecarboxylic acid 在 吡啶 、 氯化亚砜 作用下， 反应 1.17h， 生成 6-amino-1,3-dipropyl-5-<<(2,2,5,5-tetramethylcyclopentyl)carbonyl>amino>uracil
  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

文献信息

• 8-Polycycloalkyl-1,3-dipropylxanthines as potent and selective antagonists for A1-adenosine receptors
  作者：Junichi Shimada、Fumio Suzuki、Hiromi Nonaka、Akio Ishii

  DOI：10.1021/jm00083a018

  日期：1992.3

  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.