N-(4-methoxyphenyl)-1-methyl-1H-indol-5-amine | 1369116-47-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: N-(4-methoxyphenyl)-1-methyl-1H-indol-5-amine
• 英文别名: N-(4-methoxyphenyl)-1-methylindol-5-amine
• CAS: 1369116-47-1
• 化学式: C₁₆H₁₆N₂O
• 分子量: 252.316
• InChiKey: QBIXFAOPIPZOAE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  26.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(4-methoxyphenyl)-1-methyl-1H-indol-5-amine 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以51%的产率得到N-(4-methoxyphenyl)-N,1-dimethyl-1H-indol-5-amine
  参考文献：
  名称：

  Discovery of azaisoerianin derivatives as potential antitumors agents

  摘要：

  A series of N-methyl-diarylamines 2 was designed and synthesized as a novel class of CA-4 and isoCA-4 analogues. Compounds 2b and 2m showed excellent antiproliferative activity with mean GI(50) values at a nanomolar level in a diverse set of human cancer cells. These compounds also inhibited tubulin assembly at a micromolar range, arrested the cellular cycle in the G2/M phase and induced apoptosis at very low concentrations. Preliminary in vitro results revealed that 2b and 2m displayed substantial efficacy as potent antivascular agents. Docking studies indicates that these lead compounds showed a binding mode similar to those observed with isoCA-4 at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.03.032
• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 iron(II) chloride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 15.0h， 以152 mg的产率得到N-(4-methoxyphenyl)-1-methyl-1H-indol-5-amine
  参考文献：
  名称：

  通过向亚硝基芳烃中添加官能化的锌试剂来合成多官能仲胺。

  摘要：

  在乙醇中用FeCl2和NaBH4还原处理后，在乙醇中镁盐和LiCl的存在下，将官能化的芳基，杂芳基或金刚烷基锌试剂添加到各种亚硝基芳烃中，可以高收率得到相应的多官能仲胺。

  DOI：

  10.1039/c4cc08846h

文献信息

• Photoinduced Reduction of Nitroarenes and Tandem C–N Cross-Coupling with Haloarenes
  作者：Haoshi Bao、Leifeng Wang

  DOI：10.1021/acs.orglett.3c03656

  日期：2023.12.15

  photocatalytic C–N cross-coupling of nitroarenes with haloarenes has been developed using simple and cheap Ni(acac)2 as a cocatalyst. The reaction is confirmed as a stepwise process: (1) metal free photoinduced reduction of nitroarenes into aniline derivatives and (2) photo- and Ni-catalyzed C–N cross-coupling of anilines with haloarenes. The reaction conditions are simple and mild, giving high-value diarylamines

  使用简单且廉价的 Ni(acac) 2作为助催化剂，开发了硝基芳烃与卤代芳烃的高效光催化 C-N 交叉偶联。该反应被证实是一个逐步过程：（1）无金属光诱导硝基芳烃还原成苯胺衍生物，（2）苯胺与卤代芳烃的光催化和镍催化C-N交叉偶联。反应条件简单温和，可得到高价值的二芳基胺，具有良好的收率和良好的官能团耐受性。
• Dual role of nitroarenes as electrophiles and arylamine surrogates in Buchwald–Hartwig-type coupling for C–N bond construction
  作者：Zhiguo Lei、Jiaxin Yao、Yuxuan Xiao、Wenbo H. Liu、Lin Yu、Wengui Duan、Chao-Jun Li

  DOI：10.1039/d3sc06618e

  日期：——

  of aryl halides/boronic acids with amines, known as Ullmann condensation, Buchwald–Hartwig amination, and Chan–Lam coupling. However, aryl halides/boronic acids often require multi-step preparation while generating a large amount of corrosive and toxic waste, making the reaction less attractive. Herein, we present an unprecedented method for the C(sp2)–N formation via Buchwald–Hartwig-type reactions

  构建 C(sp 2 )–N 键最广泛使用的方法之一是过渡金属催化的芳基卤化物/硼酸与胺的交叉偶联，称为乌尔曼缩合、Buchwald-Hartwig 胺化和 Chan –拉姆联轴器。然而，芳基卤化物/硼酸通常需要多步制备，同时产生大量腐蚀性和有毒废物，使得该反应不太有吸引力。在此，我们提出了一种前所未有的方法，通过Buchwald-Hartwig 型反应形成 C(sp 2 )–N，使用合成上游硝基芳烃作为唯一起始原料，从而消除了对芳基卤化物和预先形成的芳基胺的需要。从硝基芳烃一步获得了多种对称的二芳基胺和三芳基胺，更重要的是，还通过一锅/两步法高选择性地合成了各种不对称的二芳基胺和三芳基胺。此外，放大实验的成功、药物中间体的后期功能化以及空穴传输材料TCTA的快速制备展示了该方案在合成化学中的实用性和实用性。机理研究表明，这种转化可能通过硝基芳烃还原原位生成的芳胺中间体进行，随后与另一种硝基芳烃发生脱硝
• Synthesis of polyfunctional secondary amines by the addition of functionalized zinc reagents to nitrosoarenes
  作者：Vasudevan Dhayalan、Christoph Sämann、Paul Knochel

  DOI：10.1039/c4cc08846h

  日期：——

  Addition of functionalized aryl, heteroaryl or adamantyl zinc reagents to various nitroso-arenes in the presence of magnesium salts and LiCl in THF produces after a reductive work-up with FeCl2 and NaBH4 in ethanol the corresponding polyfunctional secondary amines in high yields.

  在乙醇中用FeCl2和NaBH4还原处理后，在乙醇中镁盐和LiCl的存在下，将官能化的芳基，杂芳基或金刚烷基锌试剂添加到各种亚硝基芳烃中，可以高收率得到相应的多官能仲胺。
• Discovery of azaisoerianin derivatives as potential antitumors agents
  作者：Mohamed Ali Soussi、Olivier Provot、Guillaume Bernadat、Jérome Bignon、Joanna Wdzieczak-Bakala、Déborah Desravines、Joëlle Dubois、Jean-Daniel Brion、Samir Messaoudi、Mouad Alami

  DOI：10.1016/j.ejmech.2014.03.032

  日期：2014.5

  A series of N-methyl-diarylamines 2 was designed and synthesized as a novel class of CA-4 and isoCA-4 analogues. Compounds 2b and 2m showed excellent antiproliferative activity with mean GI(50) values at a nanomolar level in a diverse set of human cancer cells. These compounds also inhibited tubulin assembly at a micromolar range, arrested the cellular cycle in the G2/M phase and induced apoptosis at very low concentrations. Preliminary in vitro results revealed that 2b and 2m displayed substantial efficacy as potent antivascular agents. Docking studies indicates that these lead compounds showed a binding mode similar to those observed with isoCA-4 at the colchicine binding site of tubulin. (C) 2014 Elsevier Masson SAS. All rights reserved.