1,3-dipropyl-8-(2-butyl)xanthine | 131080-36-9

• 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: 1,3-dipropyl-8-(2-butyl)xanthine
• 英文别名: 8-sec-Butyl-1,3-dipropyl-3,7-dihydro-purine-2,6-dione；8-butan-2-yl-1,3-dipropyl-7H-purine-2,6-dione
• CAS: 131080-36-9
• 化学式: C₁₅H₂₄N₄O₂
• 分子量: 292.381
• InChiKey: YCCHHAFZTHOIHV-UHFFFAOYSA-N

物化性质

• 沸点：
  488.0±37.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 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：

  2-甲基丁酸 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 1,3-dipropyl-8-(2-butyl)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

文献信息

• Derivatives of xanthine, pharmaceutical compositions and methods of use
  申请人：Warner-Lambert Company

  公开号：US04755517A1

  公开（公告）日：1988-07-05

  The present invention is a novel disubstituted derivative of xanthine, pharmaceutical composition and method of use therefor. Activity of the novel xanthine includes particularly cognition activation.

  本发明是一种新型的黄嘌呤二取代衍生物，药物组合物及其使用方法。新型黄嘌呤的活性特别包括认知激活。
• 8-(Dicyclopropylmethyl)-1,3-dipropylxanthine: a potent and selective adenosine A1 antagonist with renal protective and diuretic activities
  作者：Junichi Shimada、Fumio Suzuki、Hiromi Nonaka、Akira Karasawa、Hideaki Mizumoto、Tetsuji Ohno、Kazuhiro Kubo、Akio Ishii

  DOI：10.1021/jm00105a072

  日期：1991.1
• BRUNS, ROBERT F.;HAMILTON, HARRIET W.
  作者：BRUNS, ROBERT F.、HAMILTON, HARRIET W.

  DOI：——

  日期：——
• US4755517A
  申请人：——

  公开号：US4755517A

  公开（公告）日：1988-07-05
• 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.