1,3-dimethyl-2,4-dioxo-6-methyl-8-(p-nitrophenyl)-1,2,3,4-tetrahydro[1,2,4]triazolo[3,4-f]purine | 348086-41-9

• 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-dimethyl-2,4-dioxo-6-methyl-8-(p-nitrophenyl)-1,2,3,4-tetrahydro[1,2,4]triazolo[3,4-f]purine
• 英文别名: 1,5,7-Trimethyl-3-(4-nitrophenyl)purino[8,7-c][1,2,4]triazole-6,8-dione
• CAS: 348086-41-9
• 化学式: C₁₅H₁₃N₇O₄
• 分子量: 355.313
• InChiKey: CFQICNBGDXTKBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  122
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-2,4-dioxo-6-methyl-8-(p-nitrophenyl)-1,2,3,4-tetrahydro[1,2,4]triazolo[3,4-f]purine 在 palladium on activated charcoal 一水合肼 作用下， 以 1,4-二氧六环 为溶剂， 反应 0.33h， 以95%的产率得到1-(4-Amino-phenyl)-3,5,7-trimethyl-1H,7H-1,2,3a,5,7,8-hexaaza-cyclopenta[a]indene-4,6-dione
  参考文献：
  名称：

  Synthesis, biological studies and molecular modeling investigation of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as potential adenosine receptor antagonists

  摘要：

  A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine structure have been synthesized, and their affinities at the four adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated. The design was based on the demonstrated approach to novel A3 adenosine receptor antagonists of adding a third ring to the xanthine structure. Unfortunately, all the synthesized compounds were completely inactive at all four adenosine receptor subtypes independently of their substitutions. Preliminary molecular modeling investigation has demonstrated that only a low degree of steric and electrostatic complementarity has been observed for all the new synthesized triazolo-purines with respect to other structurally related A3 receptor antagonists. This analysis yielded valuable information about structure-activity relationships and further design of potential adenosine receptor antagonists.

  DOI：

  10.1016/j.farmac.2005.01.008
• 作为产物：
  描述：

  1,3-二甲基-8-硝基-1H-嘌呤2,6(3H,9H)-二酮 、 N-(4-nitrophenyl)acetohydrazonoyl bromide 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 10.0h， 以85%的产率得到1,3-dimethyl-2,4-dioxo-6-methyl-8-(p-nitrophenyl)-1,2,3,4-tetrahydro[1,2,4]triazolo[3,4-f]purine
  参考文献：
  名称：

  Synthesis, biological studies and molecular modeling investigation of 1,3-dimethyl-2,4-dioxo-6-methyl-8-(substituted) 1,2,3,4-tetrahydro [1,2,4]-triazolo [3,4-f]-purines as potential adenosine receptor antagonists

  摘要：

  A new series of potential adenosine receptor antagonists with a [1,2,4]-triazolo-[3,4-f]-purine structure have been synthesized, and their affinities at the four adenosine receptor subtypes (A1, A2A, A2B and A3) have been evaluated. The design was based on the demonstrated approach to novel A3 adenosine receptor antagonists of adding a third ring to the xanthine structure. Unfortunately, all the synthesized compounds were completely inactive at all four adenosine receptor subtypes independently of their substitutions. Preliminary molecular modeling investigation has demonstrated that only a low degree of steric and electrostatic complementarity has been observed for all the new synthesized triazolo-purines with respect to other structurally related A3 receptor antagonists. This analysis yielded valuable information about structure-activity relationships and further design of potential adenosine receptor antagonists.

  DOI：

  10.1016/j.farmac.2005.01.008

文献信息

• A Simple One-Pot Synthesis of Novel [1,2,4]Triazolo[3,4-<i>f</i>]purines
  作者：Ahmad S. Shawali、Mosselhi、Nagla M. Tawfik

  DOI：10.1021/jo001626a

  日期：2001.6.1