1-allyl-8-<4-(trifluoromethyl)phenyl>3,7-dimethylxanthine

• 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-allyl-8-<4-(trifluoromethyl)phenyl>3,7-dimethylxanthine
• 英文别名: 1-Allyl-3,7-dimethyl-8-(4-trifluoromethyl-phenyl)-3,7-dihydro-purine-2,6-dione；3,7-dimethyl-1-prop-2-enyl-8-[4-(trifluoromethyl)phenyl]purine-2,6-dione
• 化学式: C₁₇H₁₅F₃N₄O₂
• 分子量: 364.327
• InChiKey: LMBBENJQZLAAHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  58.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  丙烯酰碘 、 8-<4-(trifluoromethyl)phenyl>-3,7-dimethylxanthine 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以85%的产率得到1-allyl-8-<4-(trifluoromethyl)phenyl>3,7-dimethylxanthine
  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

文献信息

• Effect of trifluoromethyl and other substituents on activity of xanthines at adenosine receptors
  作者：Kenneth A. Jacobson、Dan Shi、Carola Gallo-Rodriguez、Malcolm Manning、Christa Muller、John W. Daly、John L. Neumeyer、Leonidas Kiriasis、Wolfgang Pfleiderer

  DOI：10.1021/jm00070a007

  日期：1993.9

  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.