Bicyclo[2.2.1]heptane-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide | 136199-21-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Bicyclo[2.2.1]heptane-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide
• 英文别名: 6-Amino-5-(bicyclo[2.2.1]heptan-2-yl)carbonylamino-1,3-dipropyluracil；N-(4-amino-2,6-dioxo-1,3-dipropylpyrimidin-5-yl)bicyclo[2.2.1]heptane-2-carboxamide
• CAS: 136199-21-8
• 化学式: C₁₈H₂₈N₄O₃
• 分子量: 348.445
• InChiKey: VAVMUPBJTMWDQV-UHFFFAOYSA-N

物化性质

• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 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：

  Bicyclo[2.2.1]heptane-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide 在 sodium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.17h， 生成 8-(2-exo-norbornyl)-1,3-dipropylxanthine 、 8-(2-endo-norbornyl)-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 、 二甲基降莰烷 以to afford 4.31 g (yield: 93%) of amorphous 6-amino-5-(bicyclo[2.2.1]heptan-2-yl)carbonylamino-1,3-dipropyluracil的产率得到Bicyclo[2.2.1]heptane-2-carboxylic acid (6-amino-2,4-dioxo-1,3-dipropyl-1,2,3,4-tetrahydro-pyrimidin-5-yl)-amide
  参考文献：
  名称：

  Xanthine derivatives

  摘要：

  以下是用下列式子表示的新型黄嘌呤化合物：##STR1## 其中X.sup.1和X.sup.2各自独立地代表氧或硫; Q代表; ##STR2## 其中-----代表单键或双键；Y代表单键或烷基，n代表0或1，W.sup.1和W.sup.2各自独立地代表氢，低烷基或氨基，Z代表--CH.sub.2-, --O--, --S--或--NH--;代表 ##STR3## R.sup.1和R.sup.2各自独立地代表氢，低烷基，烯丙基或丙炔基；而R.sup.3代表氢或低烷基，当Q代表除了##STR4##之外的基团时，R.sup.1，R.sup.2和R.sup.3各自独立地代表氢或低烷基；但是，当Q为##STR5##时，R.sup.1，R.sup.2和R.sup.3不能同时为甲基；以及其药学上可接受的盐具有利尿作用、肾脏保护作用和支气管扩张作用。

  公开号：

  US05290782A1

文献信息

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

  公开号：US05290782A1

  公开（公告）日：1994-03-01

  Novel xanthine compounds represented by the following formula: ##STR1## wherein each of X.sup.1 and X.sup.2 independently represents oxygen or sulfur; and Q represents; ##STR2## where ----- represents a single bond or a double bond; Y represents a single bond or alkylene, n represents 0 or 1, each of W.sup.1 and W.sup.2 independently represents hydrogen, lower alkyl or amino, Z represents --CH.sub.2 -, --O--, --S-- or --NH--; represents ##STR3## each of R.sup.1 and R.sup.2 independently represents hydrogen, lower alkyl, allyl or propargyl; and R.sup.3 represents hydrogen or lower alkyl, and when Q represents the groups other than ##STR4## each of R.sup.1, R.sup.2 and R.sup.3 independently represents hydrogen or lower alkyl; provided that when Q is ##STR5## then R.sup.1 R.sup.2 and R.sup.3 are not simultaneously methyl; and pharmaceutically acceptable salts thereof have a diuretic effect, a renal-protecting effect and a bronchodilatory effect.

  以下是用下列式子表示的新型黄嘌呤化合物：##STR1## 其中X.sup.1和X.sup.2各自独立地代表氧或硫; Q代表; ##STR2## 其中-----代表单键或双键；Y代表单键或烷基，n代表0或1，W.sup.1和W.sup.2各自独立地代表氢，低烷基或氨基，Z代表--CH.sub.2-, --O--, --S--或--NH--;代表 ##STR3## R.sup.1和R.sup.2各自独立地代表氢，低烷基，烯丙基或丙炔基；而R.sup.3代表氢或低烷基，当Q代表除了##STR4##之外的基团时，R.sup.1，R.sup.2和R.sup.3各自独立地代表氢或低烷基；但是，当Q为##STR5##时，R.sup.1，R.sup.2和R.sup.3不能同时为甲基；以及其药学上可接受的盐具有利尿作用、肾脏保护作用和支气管扩张作用。
• 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.