4-(3,7-二甲基-2,6-二氧代-2,3,6,7-四氢-1H-嘌呤-8-基)苯磺酸 | 149981-20-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 中文名称: 4-(3,7-二甲基-2,6-二氧代-2,3,6,7-四氢-1H-嘌呤-8-基)苯磺酸
• 英文名称: 3,7-dimethyl-8-(4-sulfophenyl)xanthine
• 英文别名: 3,7-Dimethyl-8-p-sulfophenylxanthine；4-(3,7-dimethyl-2,6-dioxopurin-8-yl)benzenesulfonic acid
• CAS: 149981-20-4
• 化学式: C₁₃H₁₂N₄O₅S
• 分子量: 336.328
• InChiKey: UQHWMQWFLPDPAW-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 密度：
  1.70±0.1 g/cm3(Predicted)
• 溶解度：
  二甲基亚砜（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  丙烯酰碘 、 4-(3,7-二甲基-2,6-二氧代-2,3,6,7-四氢-1H-嘌呤-8-基)苯磺酸 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以73%的产率得到4-[2,3,6,7-四氢-3,7-二甲基-2,6-二氧代-1-(2-丙烯-1-基)-1H-嘌呤-8-基]-苯磺酸
  参考文献：
  名称：

  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors

  摘要：

  An aryl p-(trifluoromethyl) substituent increases the affinity of 1,3-disubstituted 8-phenylxanthines at A2a-adenosine receptors, while having little effect on affinity at Al-adenosine receptors. In contrast, an aryl p-(trifluoromethyl) substituent has little effect on affinity of 3,7-disubstituted and 1,3,7-trisubstituted 8-phenylxanthines. An aryl p-sulfo substituent reduces affinity of all 8-phenylxanthines at A1-and A2a-adenosine receptors. An 8-(trifluoromethyl) substituent markedly reduces affinity of 1,3-dialkylxanthines at both A1- and A2a-adenosine receptors. In contrast, 8-(trifluoromethyl)caffeine retains affinity for A2a-adenosine receptors, but does lose affinity for A1-adenosine receptors. 8-Bromo-, 8-acryl-, and 8-pent-1-enylcaffeines are also selective for A2-adenosine receptors, while 8-cyclobutylcaffeine is nonselective. 8-[trans-2-(tert-butyloxycarbonyl)vinylcaffeine is 20-fold selective for Aza vs A1 receptors.

  DOI：

  10.1021/jm00070a007
• 作为产物：
  描述：

  4-(3,7-二甲基-2,6-二氧代-2,3,6,7-四氢-1H-嘌呤-8-基)苯磺酰胺 在 三氟乙酸 、 sodium nitrite 作用下， 以95%的产率得到4-(3,7-二甲基-2,6-二氧代-2,3,6,7-四氢-1H-嘌呤-8-基)苯磺酸
  参考文献：
  名称：

  Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors

  摘要：

  An aryl p-(trifluoromethyl) substituent increases the affinity of 1,3-disubstituted 8-phenylxanthines at A2a-adenosine receptors, while having little effect on affinity at Al-adenosine receptors. In contrast, an aryl p-(trifluoromethyl) substituent has little effect on affinity of 3,7-disubstituted and 1,3,7-trisubstituted 8-phenylxanthines. An aryl p-sulfo substituent reduces affinity of all 8-phenylxanthines at A1-and A2a-adenosine receptors. An 8-(trifluoromethyl) substituent markedly reduces affinity of 1,3-dialkylxanthines at both A1- and A2a-adenosine receptors. In contrast, 8-(trifluoromethyl)caffeine retains affinity for A2a-adenosine receptors, but does lose affinity for A1-adenosine receptors. 8-Bromo-, 8-acryl-, and 8-pent-1-enylcaffeines are also selective for A2-adenosine receptors, while 8-cyclobutylcaffeine is nonselective. 8-[trans-2-(tert-butyloxycarbonyl)vinylcaffeine is 20-fold selective for Aza vs A1 receptors.

  DOI：

  10.1021/jm00070a007