N-(4-dimethylamino-butyl)-benzene-1,2-diamine | 600725-11-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N-(4-dimethylamino-butyl)-benzene-1,2-diamine
• 英文别名: 2-N-[4-(dimethylamino)butyl]benzene-1,2-diamine
• CAS: 600725-11-9
• 化学式: C₁₂H₂₁N₃
• 分子量: 207.319
• InChiKey: CULRLVUEXYPEJP-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±27.0 °C(Predicted)
• 密度：
  1.031±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  41.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-dimethylamino-butyl)-benzene-1,2-diamine 、 3-(3,4-diethyl-phenyl)-2-{[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carbonyl]-amino}-propionic acid 以29%的产率得到4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-carboxylic acid {2-(3,4-diethyl-phenyl)-1-[1-(4-dimethylamino-butyl)-1H-benzimidazol-2-yl]-ethyl}-amide
  参考文献：
  名称：

  Novel substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof

  摘要：

  本发明涉及一般式1的取代哌啶，其中R，R2至R5，A，X，Z和n的定义如权利要求1中所述，其互变异构体、对映异构体、立体异构体、混合物及其盐，特别是其与具有有价值的药理学性质，特别是CGRP-拮抗性能的无机或有机酸或碱的生理上可接受的盐，含有这些化合物的制药组合物，其用途以及其制备方法。

  公开号：

  US20030236282A1
• 作为产物：
  描述：

  4-二甲基氨基丁胺 在 溶剂黄146 、 锌 作用下， 以 四氢呋喃 为溶剂， 反应 13.0h， 生成 N-(4-dimethylamino-butyl)-benzene-1,2-diamine
  参考文献：
  名称：

  Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[a]phenazin derivatives as dual topoisomerase I/II inhibitors

  摘要：

  A novel series of benzo[a]phenazin derivatives bearing alkylamino side chains were designed, synthesized and evaluated for their topoisomerases inhibitory activity as well as cytotoxicity against four human cancer cell lines (HL-60, K-562, HeLa, and A549). These compounds were found to be dual inhibitors of topoisomerase (Topo) I and Topo II, and exhibited excellent antiproliferative activity, in particular against HL-60 cells with submicromolar IC50 values. Further mechanistic studies showed that this class of compounds acted as Topo I poisons by stabilizing the Topo I-DNA cleavage complexes and Topo II catalytic inhibitors by inhibiting the ATPase activity of hTopo II. Molecular docking studies revealed the binding modes of these compounds for Topo I and Topo II. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.01.024

文献信息

• BENZODIAZEPIN-SUBSTITUIERTE PIPERDINE ZUR VERWENDUNG IN DER BEHANDLUNG VON CARDIOVASKULÄREN ERKRANKUNGEN
  申请人：Boehringer Ingelheim Pharma GmbH & Co.KG

  公开号：EP1487821B1

  公开（公告）日：2007-03-21
• US7026312B2
  申请人：——

  公开号：US7026312B2

  公开（公告）日：2006-04-11
• US7538115B2
  申请人：——

  公开号：US7538115B2

  公开（公告）日：2009-05-26
• Design, synthesis and biological evaluation of novel 7-alkylamino substituted benzo[a]phenazin derivatives as dual topoisomerase I/II inhibitors
  作者：Bing-Lei Yao、Yan-Wen Mai、Shuo-Bin Chen、Hua-Ting Xie、Pei-Fen Yao、Tian-Miao Ou、Jia-Heng Tan、Hong-Gen Wang、Ding Li、Shi-Liang Huang、Lian-Quan Gu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2015.01.024

  日期：2015.3

  A novel series of benzo[a]phenazin derivatives bearing alkylamino side chains were designed, synthesized and evaluated for their topoisomerases inhibitory activity as well as cytotoxicity against four human cancer cell lines (HL-60, K-562, HeLa, and A549). These compounds were found to be dual inhibitors of topoisomerase (Topo) I and Topo II, and exhibited excellent antiproliferative activity, in particular against HL-60 cells with submicromolar IC50 values. Further mechanistic studies showed that this class of compounds acted as Topo I poisons by stabilizing the Topo I-DNA cleavage complexes and Topo II catalytic inhibitors by inhibiting the ATPase activity of hTopo II. Molecular docking studies revealed the binding modes of these compounds for Topo I and Topo II. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Novel substituted piperidines, pharmaceutical compositions containing these compounds, their use and processes for the preparation thereof
  申请人：Boehringer ingelheim Pharma GmbH & Co.

  公开号：US20030236282A1

  公开（公告）日：2003-12-25

  The present invention relates to substituted piperidines of general formula 1 wherein R, R 2 to R 5 , A, X, Z and n are defined as in claim 1, the tautomers, diastereomers, enantiomers, mixtures and salts thereof, particularly the physiologically acceptable salts thereof with inorganic or organic acids or bases which have valuable pharmacological properties, particularly CGRP-antagonistic properties, pharmaceutical compositions containing these compounds, the use thereof and processes for the preparation thereof.

  本发明涉及一般式1的取代哌啶，其中R，R2至R5，A，X，Z和n的定义如权利要求1中所述，其互变异构体、对映异构体、立体异构体、混合物及其盐，特别是其与具有有价值的药理学性质，特别是CGRP-拮抗性能的无机或有机酸或碱的生理上可接受的盐，含有这些化合物的制药组合物，其用途以及其制备方法。