4-(bis(5-bromo-1H-indol-3-yl)methyl)phenol | 1429404-74-9

• 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: 4-(bis(5-bromo-1H-indol-3-yl)methyl)phenol
• 英文别名: 4-[bis(5-bromo-1H-indol-3-yl)methyl]phenol
• CAS: 1429404-74-9
• 化学式: C₂₃H₁₆Br₂N₂O
• 分子量: 496.201
• InChiKey: AKBSAYPEOWUCTB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  28
• 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：
  51.8
• 氢给体数：
  3
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  5-溴吲哚 、 对羟基苯甲醛 在 Fe/Al pillared clay-425°C 作用下， 以 neat (no solvent) 为溶剂， 以95%的产率得到4-(bis(5-bromo-1H-indol-3-yl)methyl)phenol
  参考文献：
  名称：

  Fe/Al pillared clay catalyzed solvent-free synthesis of bisindolylmethanes using diversely substituted indoles and carbonyl compounds

  摘要：

  我们开发了一种快速、无溶剂的固体酸介导合成双吲哚甲烷的方法。该工艺适用于多种具有不同保护基团存活特性的底物。铁/铝柱状粘土可重复使用 5 次以上而不会明显丧失催化活性，这也是该反应的一大特点。

  DOI：

  10.1039/c2ra22258b

文献信息

• FeCl₃·6H₂O as a Mild Catalyst for Nucleophilic Substitution of Symmetrical Bis(indoyl)methanes
  作者：Chayamon Chantana、Jaray Jaratjaroonphong

  DOI：10.1021/acs.joc.0c02466

  日期：2021.2.5

  In this paper, unsymmetrical bis(indolyl)methane (BIM) and 3-alkylindole derivatives are smoothly synthesized from symmetrical BIMs with a variety of nucleophiles including heteroaromatic/aromatic compounds, allylsilane and alkynylsilane. FeCl3·6H2O is found to be a mild and highly effective catalyst for this nucleophilic substitution reaction in which N-methyl-2-phenylindole behaves as a good leaving

  在本文中，不对称双（吲哚基）甲烷（BIM）和3-烷基吲哚衍生物是由具有各种亲核试剂（包括杂芳族/芳族化合物，烯丙基硅烷和炔基硅烷）的对称BIM平稳合成的。FeCl 3 ·6H 2 O被发现是这种亲核取代反应的温和高效催化剂，其中N-甲基-2-苯基吲哚在C sp 3 -C sp 2键断裂反应中表现为良好的离去基团。操作简便，廉价且对环境友好的催化剂，温和的反应条件，宽泛的官能团耐受性和该反应策略的可扩展性是本方法的优点。
• Evaluation of bisindole as potent β-glucuronidase inhibitors: Synthesis and in silico based studies
  作者：Khalid Mohammed Khan、Fazal Rahim、Abdul Wadood、Muhammad Taha、Momin Khan、Shagufta Naureen、Nida Ambreen、Shafqat Hussain、Shahnaz Perveen、Mohammad Iqbal Choudhary

  DOI：10.1016/j.bmcl.2014.02.015

  日期：2014.4

  – were synthesized and evaluated for their in vitro β-glucuronidase inhibitory potential. Out of seventeen compounds, the analog (IC=1.62±0.04μM), (IC=1.86±0.05μM), (IC=2.80±0.29μM), (IC=3.10±0.28μM), (IC=4.30±0.08μM), (IC=18.40±0.09μM), (IC=19.90±1.05μM), (IC=20.90±0.62μM), (IC=21.50±0.77μM), and (IC=22.30±0.02μM) showed superior β-glucuronidase inhibitory activity than the standard (-saccharic acid

  双吲哚类似物 – 合成并评估其体外 β-葡萄糖醛酸酶抑制潜力。十七种化合物中，类似物 (IC=1.62±0.04μM)、(IC=1.86±0.05μM)、(IC=2.80±0.29μM)、(IC=3.10±0.28μM)、(IC=4.30±0.08μM) ）、（IC=18.40±0.09μM）、（IC=19.90±1.05μM）、（IC=20.90±0.62μM）、（IC=21.50±0.77μM）和（IC=22.30±0.02μM）表现出优异的β -葡萄糖醛酸酶抑制活性高于标准品（-糖二酸1,4-内酯，IC=48.40±1.25μM）。此外，还进行了分子对接研究，以研究双吲哚衍生物与酶的结合相互作用。这项研究发现了一类新的有效 β-葡萄糖醛酸酶抑制剂。
• Expedient Access to Indolyl-Substituted Tri- and Diarylmethanes and (±)-Colletotryptin E by Silica Sulfuric Acid Catalyzed Transindolylation
  作者：Jaray Jaratjaroonphong、Jirapat Yimyaem、Chayamon Chantana、Suthimon Boonmee

  DOI：10.1055/s-0040-1719915

  日期：2022.9

  nonsymmetrical bis(indolyl)methanes (BIMs) through transindolylation of readily available symmetrical 3,3′-BIMs with various indoles catalyzed by silica-supported sulfuric acid has been established. This approach not only provides a useful strategy for the synthesis of structurally diverse BIMs, but also provides examples of nucleophilic substitution of BIMs with aromatic and nonaromatic π-systems

  已经建立了通过容易获得的对称 3,3'-BIM 与由二氧化硅负载的硫酸催化的各种吲哚的转吲哚反应来获得一系列非对称双（吲哚基）甲烷（BIM）的便捷途径。这种方法不仅为合成结构多样的 BIMs 提供了一种有用的策略，而且还提供了用芳香族和非芳香族 π-体系对 BIMs 进行亲核取代的例子，从而形成了一个吲哚基取代的三芳基甲烷和二芳基甲烷库。此外，该方法成功应用于首次三步全合成2,3'-BIM生物碱(±)-colletotryptin E，总收率为46%。该过程的特点包括无金属工艺、廉价且环保的催化剂、温和的反应条件、广泛的官能团耐受性、良好的收率、
• 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。
• Natural Products for Biocides Discovery: Discovery of Arundine and It’s Derivatives as Novel Antiviral and Anti-Phytopathogenic-Fungus Agents
  作者：Ziwen Wang、Qingmin Wang、Ancai Liao、Shengli Jin

  DOI：10.3987/com-19-14192

  日期：——

  Plant diseases are one of the natural disasters that seriously harm agricultural production, and it is very difficult to control. The discovery of new antiviral and antifungal lead compounds becomes more and more important. Natural product arundine was found to have anti-tobacco mosaic virus (TMV) activity and anti-phytopathogenic-fungus activity for the first time. A series of arundine analogues were designed, synthesized and evaluated for their antiviral and fungicidal activities. Compound 6 with excellent antiviral activity emerged as novel antiviral lead compound. Compound 7 with 12.6-38.3 mu g/mL EC50 values against 14 plant pathogens emerged as novel antifungal lead compound. This work laid a foundation for promoting the application of arundine analogues in plant protection.