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 | 149981-21-5

• 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)苯磺酰胺
• 英文名称: 3,7-dimethyl-8-(4-sulfonamidophenyl)xanthine
• 英文别名: 3,7-Dimethyl-8-(p-sulfonamidophenyl)xanthine；4-(3,7-dimethyl-2,6-dioxopurin-8-yl)benzenesulfonamide
• CAS: 149981-21-5
• 化学式: C₁₃H₁₃N₅O₄S
• 分子量: 335.343
• InChiKey: DDFVXPNYCNTGTD-UHFFFAOYSA-N

物化性质

• 熔点：
  >300°C
• 溶解度：
  可溶于乙腈（非常轻微，加热）、DMSO（轻微）、DMF（轻微）

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 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：
  136
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  6-amino-5-(4-sulfonamidobenzoyl)-N-(methylamino)-1-methyluracil 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 1.0h， 以90%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)苯磺酰胺
  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.