N,N-diethyl-4-(1H-imidazol-1-yl)aniline | 1269166-04-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N,N-diethyl-4-(1H-imidazol-1-yl)aniline
• 英文别名: N,N-diethyl-4-imidazol-1-ylaniline
• CAS: 1269166-04-2
• 化学式: C₁₃H₁₇N₃
• 分子量: 215.298
• InChiKey: JRFPLTOMRMWDBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  21.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N,N-diethyl-4-(1H-imidazol-1-yl)aniline 在 silver(l) oxide 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  Pharmacomodulation on Gold-NHC complexes for anticancer applications – is lipophilicity the key point?

  摘要：

  A series of four new mononuclear cationic gold(I) complexes containing nitrogen functionalized N-heterocyclic carbenes (NHCs) was synthesized and fully characterized by spectroscopic methods. The X-ray structures of three complexes are presented. These lipophilic gold(I) complexes originate from a pharmacomodulation of previously described gold(I)-NHC complexes, by replacing an aliphatic spacer with an aromatic one. The Log P values of the resulting complexes increased by 0.7-1.5, depending on the substituents in comparison to the aliphatic-linker systems. The new series of complexes has been investigated in vitro for their anti -cancer activities in PC-3 (prostate cancer) and T24 (bladder cancer) cell lines and in the non-cancerous MC3T3 (osteoblast) cell line. All tested complexes show high activities against the cancer cell lines with GI(50) values lower than 500 nM. One complex (11) has been selected for further investigations. It has been tested in vitro in six cancer cell lines from different origins (prostate, bladder, lung, bone, liver and breast) and two non-cancerous cell lines (osteoblasts, fibroblasts). Moreover, cellular uptake measurements were indicative of a good bioavailability. By various biochemical assays, this complex was found to effectively inhibit the thioredoxin reductase (TrxR) and its cytotoxicity towards prostate PC-3, bladder 124 and liver HepG2 cells was found to be ROS-dependent. (C) 2018 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2018.07.070
• 作为产物：
  描述：

  咪唑 、 4-(diethylamino)phenylboronic acid 在 Cu^I-USY zeolite 作用下， 以 甲醇 为溶剂， 反应 17.0h， 以28%的产率得到N,N-diethyl-4-(1H-imidazol-1-yl)aniline
  参考文献：
  名称：

  无碱和无配体的CuI-沸石催化下的Chan–Lam型C–N交叉偶联反应

  摘要：

  致敬JF Normant教授，他是一位杰出的科学家和一个出色的人，并表彰他在有机金属化学领域的杰出成就。 抽象的 研究了各种代表性的铜（I）交换沸石在Chan-Lam交叉偶联反应中的催化潜力。Cu I -USY似乎是最好的催化剂，并被证明可以在有吸引力，简单和实用的条件下有效地促进C–N交叉偶联过程，即在空气中在无碱的情况下在甲醇中回流。 研究了各种代表性的铜（I）交换沸石在Chan-Lam交叉偶联反应中的催化潜力。Cu I -USY似乎是最好的催化剂，并被证明可以在有吸引力，简单和实用的条件下有效地促进C–N交叉偶联过程，即在空气中在无碱的情况下在甲醇中回流。

  DOI：

  10.1055/s-0036-1588652

文献信息

• Cation-Anion Interaction-Directed Molecular Design Strategy for Mechanochromic Luminescence
  作者：Gaocan Li、Feijie Song、Di Wu、Jingbo Lan、Xingyan Liu、Jie Wu、Shuaijun Yang、Dan Xiao、Jingsong You

  DOI：10.1002/adfm.201302086

  日期：2014.2

  a wide variety of applications such as sensors, memory devices, motion systems, security systems, and so forth. However, only few design principles have been disclosed, which greatly impedes the growth of mechanofluorochromic dyes. Here, a strategy of molecular design for mechanochromic luminescence is reported, based on the cation–anion interaction‐directed switching of molecular stacking. On the basis

  机械氟致变色材料在诸如传感器，存储设备，运动系统，安全系统等广泛的应用中具有巨大的潜力。然而，仅公开了很少的设计原理，这极大地阻碍了机械氟致变色染料的生长。在此，报告了基于阳离子-阴离子相互作用指导的分子堆叠转换的机械变色发光分子设计策略。在此策略的基础上，设计了一系列常见的N-杂芳族鎓荧光团，如咪唑鎓，1,2,4-三唑鎓，三唑并吡啶鎓，苯并咪唑鎓，γ-咔啉鎓和吡啶鎓盐，并被证明具有惊人的可逆机械荧光变色行为。 。
• Method for measuring an amount of LDL-cholesterol
  申请人：WAKO PURE CHEMICAL INDUSTRIES, LTD

  公开号：EP0821239A2

  公开（公告）日：1998-01-28

  The present invention is to provide a method for measuring an amount of cholesterol in low density lipoproteins (LDL-cholesterol) in a sample specifically at high accuracy and a reagent used in this method, and the present invention can attain such effect that direct measuring an amount of LDL-cholesterol by widely used automatic analyzers can be conducted by using the invention, which has not been possible after known methods.

  本发明旨在提供一种高精度测量样本中低密度脂蛋白（LDL-胆固醇）中胆固醇含量的方法以及该方法中使用的试剂，本发明可以达到这样的效果，即使用本发明可以通过广泛使用的自动分析仪直接测量 LDL-胆固醇的含量，这是已知方法无法实现的。
• US5885788A
  申请人：——

  公开号：US5885788A

  公开（公告）日：1999-03-23
• Chan–Lam-Type C–N Cross-Coupling Reactions under Base- and Ligand-Free CuI-Zeolite Catalysis
  作者：Stefan Chassaing、Patrick Pale、Tony Garnier、Randa Sakly、Mathieu Danel

  DOI：10.1055/s-0036-1588652

  日期：——

  catalyst and proved to efficiently promote C–N cross-coupling processes under attractive, simple, and practical conditions, namely refluxing in methanol under air and without any base. Various representative copper(I)-exchanged zeolites were investigated for their catalytic potential in Chan–Lam cross-coupling reactions. CuI-USY appeared as the best catalyst and proved to efficiently promote C–N cross-coupling

  致敬JF Normant教授，他是一位杰出的科学家和一个出色的人，并表彰他在有机金属化学领域的杰出成就。 抽象的 研究了各种代表性的铜（I）交换沸石在Chan-Lam交叉偶联反应中的催化潜力。Cu I -USY似乎是最好的催化剂，并被证明可以在有吸引力，简单和实用的条件下有效地促进C–N交叉偶联过程，即在空气中在无碱的情况下在甲醇中回流。 研究了各种代表性的铜（I）交换沸石在Chan-Lam交叉偶联反应中的催化潜力。Cu I -USY似乎是最好的催化剂，并被证明可以在有吸引力，简单和实用的条件下有效地促进C–N交叉偶联过程，即在空气中在无碱的情况下在甲醇中回流。
• Pharmacomodulation on Gold-NHC complexes for anticancer applications – is lipophilicity the key point?
  作者：Chen Zhang、Marie-Lise Maddelein、Raymond Wai-Yin Sun、Heinz Gornitzka、Olivier Cuvillier、Catherine Hemmert

  DOI：10.1016/j.ejmech.2018.07.070

  日期：2018.9

  A series of four new mononuclear cationic gold(I) complexes containing nitrogen functionalized N-heterocyclic carbenes (NHCs) was synthesized and fully characterized by spectroscopic methods. The X-ray structures of three complexes are presented. These lipophilic gold(I) complexes originate from a pharmacomodulation of previously described gold(I)-NHC complexes, by replacing an aliphatic spacer with an aromatic one. The Log P values of the resulting complexes increased by 0.7-1.5, depending on the substituents in comparison to the aliphatic-linker systems. The new series of complexes has been investigated in vitro for their anti -cancer activities in PC-3 (prostate cancer) and T24 (bladder cancer) cell lines and in the non-cancerous MC3T3 (osteoblast) cell line. All tested complexes show high activities against the cancer cell lines with GI(50) values lower than 500 nM. One complex (11) has been selected for further investigations. It has been tested in vitro in six cancer cell lines from different origins (prostate, bladder, lung, bone, liver and breast) and two non-cancerous cell lines (osteoblasts, fibroblasts). Moreover, cellular uptake measurements were indicative of a good bioavailability. By various biochemical assays, this complex was found to effectively inhibit the thioredoxin reductase (TrxR) and its cytotoxicity towards prostate PC-3, bladder 124 and liver HepG2 cells was found to be ROS-dependent. (C) 2018 Elsevier Masson SAS. All rights reserved.