bis(5-methoxyindol-3-yl)(4'-nitrophenyl)methane

• 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: bis(5-methoxyindol-3-yl)(4'-nitrophenyl)methane
• 英文别名: 3,3'-((4-nitrophenyl)methylene)bis(5-methoxy-1H-indole)；5-methoxy-3-[(5-methoxy-1H-indol-3-yl)-(4-nitrophenyl)methyl]-1H-indole
• 化学式: C₂₅H₂₁N₃O₄
• 分子量: 427.459
• InChiKey: PPKBVRDOQPFVNM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 、 对硝基苯甲醛 在 scandium tris(trifluoromethanesulfonate) 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到bis(5-methoxyindol-3-yl)(4'-nitrophenyl)methane
  参考文献：
  名称：

  流动化学在催化中的应用：双（吲哚基）甲烷选择性合成的新途径

  摘要：

  流动化学能够使用Sc（OTf）3催化从各种吲哚和结构不同的醛制备双（吲哚基）甲烷。该反应对吲哚的C-3功能化具有区域选择性，反应时间短，可以快速研究范围，并直接进行后处理，以利于产物分离。

  DOI：

  10.1016/j.tet.2017.02.026

文献信息

• Solvent-free multi-component synthesis of unsymmetrical bis(indolyl)alkanes with Lewis acid-surfactant-SiO₂ as nanocatalyst
  作者：Zhiqiang Wu、Gang Wang、Zhenliang Li、Enke Feng、Yanping Liang、Haijuan Zhan、Wanyi Liu

  DOI：10.1080/00397911.2021.1874016

  日期：——

  Abstract Herein we report the multicomponent synthesis of the bis(indolyl)methane derivatives in a ball mill. The reaction was carried out under solvent-free conditions using only the Lewis acid-surfactant-SiO2 composite nanocatalyst (LASSC) prepared in situ. The unsymmetrical bis(indolyl) methane derivatives containing nitro or fluorine substitution with a yield of 72%–92% were obtained in a short

  抽象的 在本文中，我们报道了在球磨机中双（吲哚基）甲烷衍生物的多组分合成。该反应在无溶剂条件下仅使用原位制备的路易斯酸表面活性剂-SiO 2复合纳米催化剂（LASSC）进行。在较短的反应时间内即可获得具有硝基或氟取代基的不对称双（吲哚基）甲烷衍生物，产率为72％–92％。我们证实了在AlCl 3 ·6H 2 O + SDS + SiO 2复合催化剂的作用下，无溶剂机械研磨制备不对称双（吲哚基）甲烷的方法具有明显的优势。最后，我们检查了该催化体系可以使用八次而活性没有明显降低。
• Selective Synthesis of Bis(indolyl)methanes Under Solvent Free Condition Using Glucopyranosylamine Derived cis-Dioxo Mo(VI) Complex as an Efficient Catalyst
  作者：Noorullah Baig、Ganesh M. Shelke、Anil Kumar、Ajay K. Sah

  DOI：10.1007/s10562-015-1648-7

  日期：2016.2

  enum(VI) complex of 4,6-O-ethylidene-β-d-glucopyranosylamine derived ligand has been used as an efficient catalyst in the selective synthesis of a series of bis(indolyl)methanes (BIMs) by condensing indole derivatives with carbonyl compounds. The adopted synthetic procedure is green in nature as solvent free reactions have been carried out using naturally occurring d-glucose derived ligands. Total

  摘要 4,6-O-亚乙基-β-d-吡喃葡萄糖胺衍生配体的顺式二氧代钼（VI）配合物已被用作通过缩合吲哚衍生物选择性合成一系列双（吲哚基）甲烷（BIMs）的有效催化剂与羰基化合物。所采用的合成程序在本质上是绿色的，因为使用天然存在的 d-葡萄糖衍生配体进行了无溶剂反应。共合成了 15 种 BIM，其中包括 4 种新的 BIM，已通过 mp、FTIR、NMR 和质谱进行表征。该催化剂在较短的反应时间内提供了良好至优异的BIMs收率，前者已循环使用5次，其催化效率没有任何显着损失。 图形摘要
• Brønsted Acidic Ionic Liquid Catalyzed Three-Component Friedel–Crafts Reaction for the Synthesis of Unsymmetrical Triarylmethanes
  作者：Uthaiwan Sirion、Suttida Rinkam、Warapong Senapak、Sarayut Watchasit、Rungnapha Saeeng

  DOI：10.1055/a-1809-7768

  日期：2022.9

  A convenient and practical method for the synthesis of unsymmetrical triarylmethanes was demonstrated through a one-pot three-component double Friedel–Crafts reaction of various aliphatic, aromatic, or heteroaromatic aldehydes with N,N-dialkylanilines and indoles by using a Brønsted acidic ionic liquid as the catalyst. This method was successfully applied under metal- and solvent-free conditions at

  通过使用布朗斯台德酸性离子液体，各种脂肪族、芳香族或杂芳香族醛与N , N - 二烷基苯胺和吲哚的一锅三组分双傅克反应，证明了一种方便实用的合成不对称三芳基甲烷的方法作为催化剂。该方法在 80 °C 的无金属和无溶剂条件下成功应用，从广泛的底物中以中等至高产率提供了相应的不对称三芳基甲烷产物。此外，通过定量NMR分析研究了该反应的机理。
• Unmodified ‘chitosan in water’ as an efficient and recyclable heterogeneous catalytic system for the synthesis of bis(indolyl)methanes
  作者：Navneet Taya、Jyoti Agarwal

  DOI：10.1016/j.apcata.2023.119539

  日期：2024.1

  and environment friendly method has been developed for the synthesis of bis(indolyl)methanes using chitosan in aqueous medium. The use of commercially available chitosan without any modifications eliminated the need of toxic metal catalysts and minimized the cost and waste generation. The optimized reaction conditions involved the use of water as solvent at reflux temperature for the model reaction between

  开发了一种简单、高效、环境友好的在水介质中使用壳聚糖合成双(吲哚基)甲烷的方法。使用未经任何修饰的市售壳聚糖消除了对有毒金属催化剂的需求，并最大限度地减少了成本和废物产生。优化的反应条件包括在回流温度下使用水作为溶剂进行吲哚和对硝基苯甲醛之间的模型反应。在该方案中，水起到反应介质和弱酸的双重作用，与催化剂一起加速反应速率。此外，这项研究还对反应范围进行了系统探索，检查了壳聚糖与各种醛和吲哚的相容性。所有反应在温和条件下顺利进行，以高达 98% 的高产率提供所需产物。还进行了可重复使用性实验，因为壳聚糖很容易回收并重复使用 5 个连续循环。
• Discovery of 3,3′-diindolylmethanes as potent antileishmanial agents
  作者：Sandip B. Bharate、Jaideep B. Bharate、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Ramesh Mudududdla、Rammohan R. Yadav、Baljinder Singh、P.R. Sharma、Sudip Maity、Baldev Singh、Ikhlas A. Khan、Ram A. Vishwakarma

  DOI：10.1016/j.ejmech.2013.02.024

  日期：2013.5

  An efficient protocol for synthesis of 3,3'-diindolylmethanes using recyclable Fe-pillared interlayered clay (Fe-PILC) catalyst under aqueous medium has been developed. All synthesized 3,3'-diindolylmethanes showed promising antileishmanial activity against Leishmania donovani promastigotes as well as axenic amastigotes. Structure-activity relationship analysis revealed that nitroaryl substituted diindolylmethanes showed potent antileishmanial activity. The 4-nitrophenyl linked 3,3'-diindolylmethane 8g was found to be the most potent antileishmanial analog showing IC50 values of 7.88 and 8.37 mu M against both L donovani promastigotes and amastigotes, respectively. Further, a pharmacophore based QSAR model was established to understand the crucial molecular features of 3,3'-diindolylmethanes essential for potent antileishmanial activity. These compounds also exhibited promising antifungal activity against Cryptococcus neoformans, wherein fluorophenyl substituted 3,3'-diindolylmethanes were found to be most potent antifungal agents. Developed synthetic protocol will be useful for economical and eco-friendly synthesis of potent antileishmanial and antifungal 3,3'-diindolylmethane class of compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.