3,5-Dimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione | 936220-85-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 3,5-Dimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione
• CAS: 936220-85-8
• 化学式: C₁₁H₁₀N₄O₂
• 分子量: 230.226
• InChiKey: RMTZWBNOVKUCRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  69.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,5-Dimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以86%的产率得到3,5,8-Trimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione
  参考文献：
  名称：

  Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors

  摘要：

  Four hybrid molecules (1 and 12-14) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. It was found that all the compounds showed better potency as adenosine receptor ligands as compared with caffeine. Among them, a compound (13) possessing a nitrogen at the delta-position of the pyridine ring (delta-N type) showed the most potent affinity for adenosine receptor A(3) subtype, while N-methylation (14) of a pyrrole ring in 13 significantly lowered the potency as adenosine receptor ligands. Compounds (1 and 12) having a nitrogen at the beta-position of the pyridine ring (beta-N type) showed lower affinity than the corresponding delta-N type compounds (13 and 14), while compounds (10, 11, and 17) lacking a pyrrole ring between the pyridine and pyrimidine rings exhibited almost no affinity to the adenosine receptor subtypes examined. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.043
• 作为产物：
  描述：

  3-氯吡啶 在 tris(dibenzylideneacetone)dipalladium (0) caesium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 42.0h， 生成 3,5-Dimethyl-3,5,8,11-tetrazatricyclo[7.4.0.02,7]trideca-1(9),2(7),10,12-tetraene-4,6-dione
  参考文献：
  名称：

  Synthesis of hybrid molecules of caffeine and eudistomin D and its effects on adenosine receptors

  摘要：

  Four hybrid molecules (1 and 12-14) of caffeine and eudistomin D, a beta-carboline alkaloid from a marine tunicate, were synthesized, and their affinity and selectivity for adenosine receptors A(1), A(2A), and A(3) were examined. It was found that all the compounds showed better potency as adenosine receptor ligands as compared with caffeine. Among them, a compound (13) possessing a nitrogen at the delta-position of the pyridine ring (delta-N type) showed the most potent affinity for adenosine receptor A(3) subtype, while N-methylation (14) of a pyrrole ring in 13 significantly lowered the potency as adenosine receptor ligands. Compounds (1 and 12) having a nitrogen at the beta-position of the pyridine ring (beta-N type) showed lower affinity than the corresponding delta-N type compounds (13 and 14), while compounds (10, 11, and 17) lacking a pyrrole ring between the pyridine and pyrimidine rings exhibited almost no affinity to the adenosine receptor subtypes examined. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.02.043