6H,12H-5,11-methanodibenzo[b,f ][1,5]diazocine-2,8-dicarboxylic acid diethyl ester | 926667-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 6H,12H-5,11-methanodibenzo[b,f ][1,5]diazocine-2,8-dicarboxylic acid diethyl ester
• 英文别名: dimethyl ester Troger's base；dimethyl 1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaene-5,13-dicarboxylate
• CAS: 926667-33-6
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: QERIYURRRINDLE-UHFFFAOYSA-N

物化性质

• 熔点：
  230-231 °C
• 沸点：
  550.4±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  59.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6H,12H-5,11-methanodibenzo[b,f ][1,5]diazocine-2,8-dicarboxylic acid diethyl ester 在 lithium aluminium tetrahydride 、 silica gel 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 为溶剂， 反应 24.0h， 生成 6H,12H-5,11-methanodibenzo[b,f] [1,5]diazocine-2,8-dicarbaldehyde
  参考文献：
  名称：

  Stabilization and Structural Alteration of the G-Quadruplex DNA Made from the Human Telomeric Repeat Mediated by Tröger’s Base Based Novel Benzimidazole Derivatives

  摘要：

  Ligand-induced stabilization of the G-quadruplex DNA structure derived from the single-stranded 3'-overhang of the telomeric DNA is an attractive strategy for the inhibition of the telomerase activity. The agents that can induce/stabilize a DNA sequence into a G-quadruplex structure are therefore potential anticancer drugs. Herein we present the first report of the interactions of two novel bisbenzimidazoles (TBBz1 and TBBz2) based on Troger's base skeleton with the G-quadruplex DNA (G4DNA). These Troger's base molecules stabilize the G4DNA derived from a human telomeric sequence. Evidence of their strong interaction with the G4DNA has been obtained from CD spectroscopy, thermal denaturation, and UV-vis titration studies. These ligands also possess significantly higher affinity toward the G4DNA over the duplex DNA. The above results obtained are in excellent agreement with the biological activity, measured in vitro using a modified TRAP assay. Furthermore, the ligands are selectively more cytotoxic toward the cancerous cells than the corresponding noncancerous cells. Computational studies suggested that the adaptive scaffold might allow these ligands to occupy not only the G-quartet planes but also the grooves of the G4DNA.

  DOI：

  10.1021/jm300442r
• 作为产物：
  描述：

  聚合甲醛 、 4-氨基苯甲酸甲酯 在 三氟乙酸 作用下， 反应 60.0h， 以23%的产率得到6H,12H-5,11-methanodibenzo[b,f ][1,5]diazocine-2,8-dicarboxylic acid diethyl ester
  参考文献：
  名称：

  对称二酯官能化 Tröger 碱基类似物的合成

  摘要：

  通过在芳环上加入给电子基团和/或提高苯胺单元的溶解度，酯官能化的 Troger 碱类似物的产率得到显着提高。除了 2,8-二酯化合物外，1,7-、3,9- 和 4,10-二酯官能化的 Troger 碱类似物也是首次制备。

  DOI：

  10.1002/ejoc.201000086