3,3'-((4-fluorophenyl)methylene)bis(5-bromo-1H-indole) | 1228150-86-4

• 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'-((4-fluorophenyl)methylene)bis(5-bromo-1H-indole)
• 英文别名: Topoisomerase I inhibitor 9；5-bromo-3-[(5-bromo-1H-indol-3-yl)-(4-fluorophenyl)methyl]-1H-indole
• CAS: 1228150-86-4
• 化学式: C₂₃H₁₅Br₂FN₂
• 分子量: 498.192
• InChiKey: QHISLSGSRBIKOS-UHFFFAOYSA-N

物化性质

• 熔点：
  198-202 °C
• 沸点：
  635.940±50.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.694±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 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：
  31.6
• 氢给体数：
  2
• 氢受体数：
  1

制备方法与用途

Topoisomerase I inhibitor 9（化合物3d）是一种莱ishmania topoisomerase IB抑制剂。实验结果显示，Topoisomerase I inhibitor 9 对利什曼原虫的promastigotes具有抗活性，其IC50值大于34.81 μM。

反应信息

• 作为反应物：
  描述：

  3,3'-((4-fluorophenyl)methylene)bis(5-bromo-1H-indole) 、 alkaline earth salt of/the/ methylsulfuric acid 在 potassium hydroxide 作用下， 以 二甲基亚砜 为溶剂， 反应 3.25h， 以84%的产率得到1-(4-fluorobenzenesulphonyl)-3-((1-(4-fluorobenzenesulphonyl)-5-bromo-1H-indol-3-yl)(4-fluorophenyl)methyl)-5-bromo-1H-indole
  参考文献：
  名称：

  A new class of bactericidal agents against S. aureus, MRSA and VRE derived from bisindolylmethane

  摘要：

  A series of bisindolylmethanes (BIMs) (1a-7j) including hybrid BIMs 6a-6c were prepared for bioevaluation. The results of initial antimicrobial screening of compounds 1a-6c showed compounds 2b, 2m, 4a and 5b to be the most potent inhibitors, exhibiting MIC as well as MBC values equal to or less than that of ciprofloxacin (0.5-2 mu g/mL) against Staphylococcus aureus, MRSA and VRE. Compound 2m was selected further to study the effect of N,N' disubstitution towards antibacterial and antitumor activity. It was observed that substitution at N,N' position (7a-7j) of 2m diminishes its antibacterial activity though in vitro antitumour activity against a panel of prostate, cervical and lung cancer cell lines remains more or less intact.

  DOI：

  10.1007/s00044-013-0764-4
• 作为产物：
  描述：

  5-溴吲哚 、 对氟苯甲醛 在 1-(3,4-dichlorobenzenesulfonyl)-3-methyl-1H-imidazolium chloride 作用下， 以 水 为溶剂， 反应 2.17h， 以93%的产率得到3,3'-((4-fluorophenyl)methylene)bis(5-bromo-1H-indole)
  参考文献：
  名称：

  Efficient Green Synthesis of Bis(3-indolyl)phenylmethanes Catalyzed by 1- (Benzenesulfonyl)-3-methyl-1H-imidazolium Chlorides

  摘要：

  通过无溶剂方法获得的 1-(苯磺酰基)-3-甲基-1H-咪唑鎓氯化物催化了吲哚与各种醛类在水介质中的反应，生成相应的双（3-吲哚基）苯基甲烷。优化反应条件后，在短时间内获得了极高的产率。使用热重分析法研究了所有 1-(苯磺酰基)-3-甲基-1H-咪唑鎓氯化物的热特性。

  DOI：

  10.2174/157017861010131126121040

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。
• 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、
• Potassium persulfate-glucose mediated synthesis of 3,3′-Bis(indolyl)methanes from arylacetic acid and indoles in water
  作者：Harish K Indurthi、Samarpita Das、Pallavi Saha、Saurabh N Koli、Deepak K Sharma

  DOI：10.1016/j.molstruc.2024.137959

  日期：2024.7

  An efficient and eco-friendly method has been developed for the preparation of 3,3′-bis(indolyl)methanes from indoles and aryl acetic acid is reported. The conversion of aryl acetic acid to their corresponding carbonyl compounds, and subsequent condensation with indoles was prompted by KSO in presence of glucose in water. The metal-free reaction with room temperature conditions, and wide substrate

  据报道，开发了一种高效且环保的方法，用于从吲哚和芳基乙酸制备 3,3'-双（吲哚基）甲烷。在水中葡萄糖存在下，KSO 促进芳基乙酸转化为其相应的羰基化合物，并随后与吲哚缩合。室温条件下的无金属反应、宽底物范围和良好的官能团耐受性是该方法的显着特征。
• 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.
• Das, Biswanath; Kumar, Rathod Aravind; Aruna, Danavath, Indian Journal of Heterocyclic Chemistry, 2010, vol. 19, # 3, p. 295 - 296
  作者：Das, Biswanath、Kumar, Rathod Aravind、Aruna, Danavath、Kashanna, Jajula

  DOI：——

  日期：——