3,3'-((2-fluorophenyl)methylene)bis(1H-indole)

• 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: 3,3'-((2-fluorophenyl)methylene)bis(1H-indole)
• 英文别名: 3,3'-[(2-fluorophenyl)methanediyl]bis(1H-indole)；3-[(2-fluorophenyl)-(1H-indol-3-yl)methyl]-1H-indole
• 化学式: C₂₃H₁₇FN₂
• 分子量: 340.4
• InChiKey: DEQLKGFEIGOTAX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  31.6
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3'-((2-fluorophenyl)methylene)bis(1H-indole) 在 盐酸 、 重铬酸吡啶 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以56%的产率得到(2-fluorophenyl)di(1H-indol-3-yl)methylium chloride
  参考文献：
  名称：

  Optimization of novel oxidative DIMs as Nur77 modulators of the Nur77-Bcl-2 apoptotic pathway

  摘要：

  DOI：

  10.1016/j.ejmech.2020.113020
• 作为产物：
  描述：

  2-氟苯甲醛 在 四氯化锡 、 溶剂黄146 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 1.0h， 生成 3,3'-((2-fluorophenyl)methylene)bis(1H-indole)
  参考文献：
  名称：

  Asymmetric aza-Friedel–Crafts reaction of indoles induced by O-pivaloylated d-galactosylamine as the chiral auxiliary

  摘要：

  The diastereoselective formation of beta-N-glycosidically linked 3-indolyl methanamine derivatives 5 has been achieved with high yield via an aza-Friedel-Crafts reaction. The reaction was performed by using O-pivaloylated galactosylamine 1 as a chiral template and SnCl4 combining TBAI as catalyst in DCM at -50 degrees C. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.03.115

文献信息

• Development of an imidazole salt catalytic system for the preparation of bis(indolyl)methanes and bis(naphthyl)methane
  作者：Xu Wang、Courtney C. Aldrich

  DOI：10.1371/journal.pone.0216008

  日期：——

  Imidazolium salts are shown to catalyze the rapid room temperature reaction of indoles or naphthol with aldehydes to provide bis(indolyl)methanes or bis(naphthol)methane in excellent yields and the reaction proceeds optimally in dichloromethane with no base additives. The reaction exhibits a broad substrate tolerance and occurs through nucleophilic activation of the indoles and naphthols through a

  已显示咪唑鎓盐催化吲哚或萘酚与醛的快速室温反应，从而以优异的收率提供双（吲哚基）甲烷或双（萘酚）甲烷，并且该反应在无碱添加剂的二氯甲烷中最佳进行。该反应表现出广泛的底物耐受性，并且通过阳离子-π相互作用通过吲哚和萘酚的亲核活化而发生。
• Solventless Mechanosynthesis Of <i>Bis</i>(Indolyl)Methanes
  作者：Shashank N. Mhaldar、Ketan S. Mandrekar、Mukund K. Gawde、Rajdatt V. Shet、Santosh G. Tilve

  DOI：10.1080/00397911.2018.1542732

  日期：2019.1.2

  Abstract Ball-milling technique as a solvent-free and an alternative green process was investigated for the eco-benign synthesis of bis(indolyl)methanes (BIMs) from various aldehydes and selected ketones with indoles in high yields. The present methodology has several advantages such as simple procedure, good yields, mild conditions, and reduced environmental consequences. The silica gel acts both

  摘要 球磨技术作为一种无溶剂和替代的绿色工艺进行了研究，用于以高产率从各种醛和选定的酮与吲哚合成双（吲哚基）甲烷（BIMs）。本方法具有几个优点，例如程序简单、产量高、条件温和、环境影响小。硅胶既是研磨介质又是酸催化剂。该技术的实用性通过合成 17 个 BIM 库来证明，其中包括两种天然产物三吲哚啉和三（1H-吲哚-3-基）甲烷。图形概要
• Facile access to bis(indolyl)methanes by copper-catalysed alkylation of indoles using alcohols under air
  作者：Ngoc-Khanh Nguyen、Duc Long Tran、Tran Quang Hung、Tra My Le、Nguyen Thi Son、Quang Thang Trinh、Tuan Thanh Dang、Peter Langer

  DOI：10.1016/j.tetlet.2021.152936

  日期：2021.3

  of many alkaloid and bioactive compounds (anti-inflammatory, anticancer, antiobesity, antimicrobial, etc.). Herein, we have reported an air stable and convenient Cu(OAc)2 catalyst for alkylation of indoles with alcohols to give bis(3-indolyl)methanes in very good yields.

  双（3-吲哚基）甲烷（BIM）非常重要，并存在于许多生物碱和生物活性化合物（抗炎，抗癌，抗肥胖，抗微生物等）的结构中。在这里，我们已经报道了一种空气稳定且方便的Cu（OAc）2催化剂，用于用醇将吲哚烷基化以非常好的收率得到双（3-吲哚基）甲烷。
• Enzymatic approach to cascade synthesis of bis(indolyl)methanes in pure water
  作者：Yajie Fu、Zeping Lu、Ke Fang、Xinyi He、Huajin Xu、Yi Hu

  DOI：10.1039/c9ra10014h

  日期：——

  A mild, efficient, and green protocol was developed for the synthesis of bis(indolyl)methanes catalyzed by lipase TLIM through the cascade reactions of indole with aldehydes in pure water. This methodology offers many superiorities such as excellent yields, wide substrate range, simple procedure, reusable and minimal amount of catalyst, and the ability to be scaled up.

  开发了一种温和、高效、绿色的方案，用于通过吲哚与醛在纯水中的级联反应，在脂肪酶 TLIM 催化下合成双（吲哚基）甲烷。该方法具有许多优势，例如产率高、底物范围广、程序简单、可重复使用且催化剂用量最少，以及放大的能力。
• [EN] OXIDIZED BIS(3-INDOLYL)METHANES AND USES THEREOF<br/>[FR] BIS(3-INDOLYL)MÉTHANES OXYDÉS ET UTILISATIONS ASSOCIÉES
  申请人：SANFORD BURNHAM PREBYS MEDICAL DISCOVERY INST

  公开号：WO2019183527A1

  公开（公告）日：2019-09-26

  Disclosed herein are compounds capable of inducing apoptosis through promoting Nur77 interaction with Bcl-2 and through modulating mitochondrial activities. Also disclosed herein are compositions and methods using these compounds and compositions. Nur77 is a key regulator of Bcl-2 activities and is capable of converting Bcl-2 from an anti-apoptotic protein to a pro-apoptotic protein. Small molecules that directly modulate the Nur77/Bcl-2 apoptotic pathways are promising for treating diseases with abnormal levels of Bcl-2, Nur77, or combinations thereof, including cancers.

  本文揭示了一些化合物，能够通过促进Nur77与Bcl-2的相互作用以及调节线粒体活性来诱导细胞凋亡。同时，本文还揭示了使用这些化合物和组合物的组成和方法。Nur77是Bcl-2活性的关键调节因子，能够将Bcl-2从抗凋亡蛋白转变为促凋亡蛋白。直接调节Nur77/Bcl-2凋亡途径的小分子对于治疗Bcl-2、Nur77或两者组合异常水平的疾病，包括癌症，是很有前途的。