1,3-dipropyl-8-{2-hydroxy-4-[(carboxymethyl)oxy]phenyl}xanthine | 112683-66-6

• 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-hydroxy-4-[(carboxymethyl)oxy]phenyl}xanthine
• 英文别名: [4-(2,6-Dioxo-1,3-dipropyl-2,3,6,7-tetrahydro-1H-purin-8-yl)-3-hydroxy-phenoxy]-acetic acid；2-[4-(2,6-dioxo-1,3-dipropyl-7H-purin-8-yl)-3-hydroxyphenoxy]acetic acid
• CAS: 112683-66-6
• 化学式: C₁₉H₂₂N₄O₆
• 分子量: 402.407
• InChiKey: WUVZVUXLLQCNSO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  136
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1,3-dipropyl-8-{2-hydroxy-4-[(carboxymethyl)oxy]phenyl}xanthine 在 ammonium hydroxide 、 氯化亚砜 作用下， 生成 1,3-dipropyl-8-{2-hydroxy-4-[(carbamoylmethyl)oxy]phenyl}xanthine
  参考文献：
  名称：

  8-Aryl- and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors

  摘要：

  A series of 1,3-dipropylxanthines were prepared with a variety of substituents at the 8-position. These included 8-aryl and 8-cycloalkyl groups. Polar carboxylate and carboxamide moieties were introduced as aryl substituents to increase water solubility. 1,3-Dipropyl-8-[2-hydroxy-4-[(carboxymethyl)oxy]phenyl]xanthine provided a functionalized congener with high potency (Ki = 37 nM) and selectivity (54-fold) for A1-adenosine receptors. This congener was used for preparation of a series of other analogues, some with higher potency and some with higher selectivity. 8-Cyclopentyl- and 8-cyclohexyl-1,3-dipropylxanthines were both very potent (Ki = 1-1.5 nM) and selective for A1 receptors, while 8-cycloalkylmethyl analogues were 10-fold less potent, but still very selective for A1 receptors. 8-Piperidinyl and 8-pyrazinyl analogues had very low activities as adenosine receptor antagonists.

  DOI：

  10.1021/jm00398a020
• 作为产物：
  描述：

  ethyl 2-(4-formyl-3-hydroxyphenoxy)acetate 在 sodium hydroxide 、 三氯化铁 作用下， 以 甲醇 、 乙醇 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.58h， 生成 1,3-dipropyl-8-{2-hydroxy-4-[(carboxymethyl)oxy]phenyl}xanthine
  参考文献：
  名称：

  8-Aryl- and 8-cycloalkyl-1,3-dipropylxanthines: further potent and selective antagonists for A1-adenosine receptors

  摘要：

  A series of 1,3-dipropylxanthines were prepared with a variety of substituents at the 8-position. These included 8-aryl and 8-cycloalkyl groups. Polar carboxylate and carboxamide moieties were introduced as aryl substituents to increase water solubility. 1,3-Dipropyl-8-[2-hydroxy-4-[(carboxymethyl)oxy]phenyl]xanthine provided a functionalized congener with high potency (Ki = 37 nM) and selectivity (54-fold) for A1-adenosine receptors. This congener was used for preparation of a series of other analogues, some with higher potency and some with higher selectivity. 8-Cyclopentyl- and 8-cyclohexyl-1,3-dipropylxanthines were both very potent (Ki = 1-1.5 nM) and selective for A1 receptors, while 8-cycloalkylmethyl analogues were 10-fold less potent, but still very selective for A1 receptors. 8-Piperidinyl and 8-pyrazinyl analogues had very low activities as adenosine receptor antagonists.

  DOI：

  10.1021/jm00398a020

文献信息

• SHAMIM, M. T.;UKENA, D.;PADGETT, W. L.;HONG, O.;DALY, J. W., J. MED. CHEM., 31,(1988) N 3, 613-617
  作者：SHAMIM, M. T.、UKENA, D.、PADGETT, W. L.、HONG, O.、DALY, J. W.

  DOI：——

  日期：——