(±)-di-tert-butyl 4,4'-(((6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(piperazine-1-carboxylate) | 1624286-19-6

• 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: (±)-di-tert-butyl 4,4'-(((6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(piperazine-1-carboxylate)
• 英文别名: Tert-butyl 4-[2-[[13-[2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]ethoxy]-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaen-5-yl]oxy]ethyl]piperazine-1-carboxylate；tert-butyl 4-[2-[[13-[2-[4-[(2-methylpropan-2-yl)oxycarbonyl]piperazin-1-yl]ethoxy]-1,9-diazatetracyclo[7.7.1.02,7.010,15]heptadeca-2(7),3,5,10(15),11,13-hexaen-5-yl]oxy]ethyl]piperazine-1-carboxylate
• CAS: 1624286-19-6
• 化学式: C₃₇H₅₄N₆O₆
• 分子量: 678.872
• InChiKey: YFGZGGREZQHOHB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  90.5
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  对正丙氧基苯胺 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 乙腈 为溶剂， 反应 48.0h， 生成 (±)-di-tert-butyl 4,4'-(((6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl)bis(oxy))bis(ethane-2,1-diyl))bis(piperazine-1-carboxylate)
  参考文献：
  名称：

  Discovery of Tröger's base analogues as selective inhibitors against human breast cancer cell line: Design, synthesis and cytotoxic evaluation

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2014.08.044