(+/-)-N,N,2,8-tetramethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocin-13-amine | 1338997-05-9

• 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: (+/-)-N,N,2,8-tetramethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocin-13-amine
• 英文别名: 2,8-dimethyl-13-(N,N-dimethylamino)-6H,12H-5,11-methano-dibenzo[b,f][1,5]diazocine；N,N,5,13-tetramethyl-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaen-17-amine
• CAS: 1338997-05-9
• 化学式: C₁₉H₂₃N₃
• 分子量: 293.412
• InChiKey: OGHDVGBSUHSCKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  9.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  TROGER碱 、 N,N-二甲基甲酰胺 在 三氯氧磷 作用下， 反应 2.0h， 以72%的产率得到(+/-)-N,N,2,8-tetramethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocin-13-amine
  参考文献：
  名称：

  在 Vilsmeier-Haack 条件下区域选择性合成二甲氨基-或芳烷基氨基-''冠冕' Tröger's 碱基类似物

  摘要：

  在典型的 Vilsmeier-Haack 条件下，Troger 的碱在二苯并 [b,f][1,5] 重氮辛系统的甲烷桥上发生区域选择性二甲氨基或芳烷基氨基取代，揭示了迄今为止未知的反应模式。反应的区域选择性是通过核磁共振光谱和 X 射线晶体学确定的。这种反应的主要特点是它的普遍性；它与 Troger 底座上的不同取代模式兼容，并且可以与 DMF 以及其他甲酰胺一起使用。该反应的广泛范围已被用于合成几种不常见的 Troger 碱类似物。

  DOI：

  10.1002/ejoc.201100804

文献信息

• Synthesis of new derivatives from a Tröger base via exchange of the methano bridge with carbonyl compounds
  作者：Mariappan Periasamy、Sundaram Suresh、Sakilam Satishkumar

  DOI：10.1016/j.tetasy.2012.01.009

  日期：2012.1

  method has been developed for the preparation of new Tröger base derivatives by an exchange reaction with the methano bridge of rac-Tröger base derivatives with carbonyl compounds in the presence of TiCl4 or POCl3. The use of chiral (S,S)-N,N-bis(α-methylbenzyl)formamide as a carbonyl compound gave the corresponding methano Tröger base derivatives with the diastereomeric ratios of up to 77:23.

  已经开发了一种简单的一锅法，用于通过在TiCl 4或POCl 3的存在下与rac- Tröger碱衍生物的甲醇桥与羰基化合物进行交换反应来制备新的Tröger碱衍生物。使用手性（S，S）-N，N-双（α-甲基苄基）甲酰胺作为羰基化合物可得到相应的亚甲基Tröger碱衍生物，其非对映体比例高达77:23。
• Reaction of Tröger’s base analogues with Vilsmeier reagents
  作者：Qasim M. Malik、Andrew B. Mahon、Donald C. Craig、Andrew C. Try

  DOI：10.1016/j.tet.2011.08.095

  日期：2011.11

  As part of a program aimed at introducing functionality onto the Tröger’s base framework post-synthesis, we investigated the formylation reaction of Tröger’s base analogues with Vilsmeier reagents. We found that rather than the anticipated reaction at the aryl rings, these compounds react with Vilsmeier reagents to afford compounds with a modified strap, whereby the apical methylene group is replaced

  作为旨在将功能引入Tröger的基础合成后程序的程序的一部分，我们研究了Tröger的基础类似物与Vilsmeier试剂的甲酰化反应。我们发现，与预期的在芳基环上的反应不同，这些化合物与Vilsmeier试剂反应生成带有修饰条带的化合物，从而顶端的亚甲基被带有N，N-二取代胺的亚甲基条带取代。
• Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation
  作者：Bhaskar Reddy Manda、Manjula Alla、Roopa Jones Ganji、Anthony Addlagatta

  DOI：10.1016/j.ejmech.2014.08.044

  日期：2014.10

  A library of structurally diverse Troger's base analogues has been constructed via unusual amination of methylene bridge employing Vilsmeier-Haack conditions as well as by the incorporation of five and six membered heterocycles on the aromatic core of Troger's base framework. The constructed structurally diverse frameworks were evaluated for their cytotoxic activities against a panel of three human cancer lines A549 (lung adenocarcinoma), MDAMB-231 (breast) and SK-N-SH (neuroblastoma). From the activity profile obtained, a redesign of Troger's base analogues led to the construction of more potent molecular entities. The study led to development of a series of compounds with MDAMB-231 cell line specific cytotoxicity. Of the 30 compounds synthesized and evaluated, 7 compounds were found to possess cytotoxicity that is equivalent or better than standard drug doxorubicin against MDAMB-231 cell line while only one compound was found to be active against SK-N-SH cell line. (c) 2014 Elsevier Masson SAS. All rights reserved.