N¹-[3-(diethylamino)propyl]-1,2-phenylenediamine | 91971-96-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: N¹-[3-(diethylamino)propyl]-1,2-phenylenediamine
• 英文别名: N1-[3-(diethylamino)propyl]benzene-1,2-diamine；2-N-[3-(diethylamino)propyl]benzene-1,2-diamine
• CAS: 91971-96-9
• 化学式: C₁₃H₂₃N₃
• mdl: MFCD11187219
• 分子量: 221.346
• InChiKey: NACVAVUSALLWRS-UHFFFAOYSA-N

物化性质

• 沸点：
  168-170 °C(Press: 3 Torr)
• 密度：
  1.017±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.538
• 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：

  N¹-[3-(diethylamino)propyl]-1,2-phenylenediamine 在 5%-palladium/activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 反应 88.0h， 生成 (E)-5-[3-(diethylamino)propyl]-3-isobutylimino-2-(4-ethoxyphenyl)amino-3,5-dihydrophenazine
  参考文献：
  名称：

  Riminophenazine 衍生物作为潜在的抗结核药物：合成、生物学和电化学评估

  摘要：

  已经设计并合成了一系列新的 riminophenazine 衍生物，在 N-5 处具有可电离的烷基取代基，并在 C-3 亚氨基氮、C-8 处和侧基芳基上具有多种取代基。使用对结核分枝杆菌H 37 Rv 的体外活性、哺乳动物细胞毒性和循环伏安法测定的化合物的氧化还原电位作为措施，对亲脂性、氧化还原电位和抗分枝杆菌活性之间的关系进行了初步研究。结果显示与 C-8 替代相关的活动“悬崖”（10l和10m)，连同定义的氧化还原活性，指出一类新的 riminophenazines 作为具有合理活性 (MIC 99 ~1 µM) 的潜在抗结核剂。

  DOI：

  10.3390/molecules26144200
• 作为产物：
  描述：

  N,N-diethyl-N'-(2-nitro-phenyl)-propane-1,3-diamine 在 5%-palladium/activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以43%的产率得到N¹-[3-(diethylamino)propyl]-1,2-phenylenediamine
  参考文献：
  名称：

  Riminophenazine 衍生物作为潜在的抗结核药物：合成、生物学和电化学评估

  摘要：

  已经设计并合成了一系列新的 riminophenazine 衍生物，在 N-5 处具有可电离的烷基取代基，并在 C-3 亚氨基氮、C-8 处和侧基芳基上具有多种取代基。使用对结核分枝杆菌H 37 Rv 的体外活性、哺乳动物细胞毒性和循环伏安法测定的化合物的氧化还原电位作为措施，对亲脂性、氧化还原电位和抗分枝杆菌活性之间的关系进行了初步研究。结果显示与 C-8 替代相关的活动“悬崖”（10l和10m)，连同定义的氧化还原活性，指出一类新的 riminophenazines 作为具有合理活性 (MIC 99 ~1 µM) 的潜在抗结核剂。

  DOI：

  10.3390/molecules26144200

文献信息

• 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。
• Parallel synthesis of a series of potentially brain penetrant aminoalkyl benzoimidazoles
  作者：Iolanda Micco、Arianna Nencini、Joanna Quinn、Hendrick Bothmann、Chiara Ghiron、Alessandro Padova、Silvia Papini

  DOI：10.1016/j.bmc.2007.11.068

  日期：2008.3

  Alpha7 agonists were identified via GOLD (CCDC) docking in the putative agonist binding site of an alpha7 homology model and a series of aminoalkyl benzoimidazoles was synthesised to obtain potentially brain penetrant drugs. The array was prepared starting from the reaction of ortho-fluoronitrobenzenes with a selection of diamines, followed by reduction of the nitro group to obtain a series of monoalkylated phenylene diamines. N,N'-Carbonyidiimidazole (CDI) mediated acylation, followed by a parallel automated work-up procedure, afforded the monoacylated phenylenediamines which were cyclised under acidic conditions. Parallel work-up and purification afforded the array products in good yields and purities with a robust parallel methodology which will be useful for other libraries. Screening for alpha7 activity revealed compounds with agonist activity for the receptor. (C) 2007 Elsevier Ltd. All rights reserved.
• 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.
• 492. Inhibitors of flavoprotein enzymes
  作者：R. B. Barlow

  DOI：10.1039/jr9510002225

  日期：——
• 9-(Dialkylaminoalkyl)-isoalloxazines
  作者：Frank Kipnis、Nathan Weiner、Paul E. Spoerri

  DOI：10.1021/ja01196a016

  日期：1947.4