6-amino-1,3-dipropyl-5-<<(1-adamantyl)acetyl>amino>uracil | 136199-23-0

• 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-<<(1-adamantyl)acetyl>amino>uracil
• 英文别名: 6-Amino-5-(adamantan-1-yl)acetylamino-1,3-dipropyluracil；2-(1-adamantyl)-N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)acetamide
• CAS: 136199-23-0
• 化学式: C₂₂H₃₄N₄O₃
• 分子量: 402.537
• InChiKey: OFXWKOQYOXNNPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.77
• 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-<<(1-adamantyl)acetyl>amino>uracil 在 三氯氧磷 作用下， 反应 2.0h， 生成 8-(1-adamantyl)methyl-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
• 作为产物：
  描述：

  5,6-二氨基-1,3-二丙基嘧啶-2,4(1H,3H)-二酮 、 1-金刚烷乙酸 在 盐酸 、 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 2.0h， 以100%的产率得到6-amino-1,3-dipropyl-5-<<(1-adamantyl)acetyl>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

• Xanthine compounds
  申请人：Kyowa Hakko Kogyo Co., Ltd

  公开号：US05525607A1

  公开（公告）日：1996-06-11

  Novel xanthine compounds represented by the following formula: ##STR1## wherein each of R.sup.1, R.sup.2 and R.sup.3 independently represents hydrogen or lower alkyl; each of X.sup.1 and X.sup.2 independently represents oxygen or sulfur; and Q represents: ##STR2## The compounds are useful as a diuretic, a renal-protecting agent and bronchodilator.

  以下式子所代表的新型黄嘌呤化合物：##STR1## 其中R.sup.1、R.sup.2和R.sup.3各自独立地代表氢或低碳基；X.sup.1和X.sup.2各自独立地代表氧或硫；Q代表：##STR2## 这些化合物可用作利尿剂、肾保护剂和支气管扩张剂。
• US5290782A
  申请人：——

  公开号：US5290782A

  公开（公告）日：1994-03-01
• US5525607A
  申请人：——

  公开号：US5525607A

  公开（公告）日：1996-06-11
• 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.