2-(2,2-di(1H-indol-3-yl)ethyl)isoindoline-1,3-dione | 457057-77-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异吲哚及其衍生物
• 英文名称: 2-(2,2-di(1H-indol-3-yl)ethyl)isoindoline-1,3-dione
• 英文别名: 2-[2,2-bis(1H-indol-3-yl)ethyl]isoindole-1,3-dione
• CAS: 457057-77-1
• 化学式: C₂₆H₁₉N₃O₂
• 分子量: 405.456
• InChiKey: PWSIPTGNHSFWHZ-UHFFFAOYSA-N

物化性质

• 熔点：
  208-210 °C(Solv: dichloromethane (75-09-2); ligroine (8032-32-4))
• 沸点：
  688.7±55.0 °C(Predicted)
• 密度：
  1.400±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  69
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(2,2-di(1H-indol-3-yl)ethyl)isoindoline-1,3-dione 在 hydrazine hydrate 、 三乙胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 23.0h， 生成 N-(2,2-di(1H-indol-3-yl)ethyl)benzamide
  参考文献：
  名称：

  生物碱st reptindole及其衍生物在防治植物病毒病菌病中的应用

  摘要：

  本发明涉及一种生物碱streptindole及其衍生物在治疗植物病毒病菌病中的应用，本发明首次发现streptindole及其衍生物I‑1～I‑14表现出很好的抗植物病毒病菌活性，能很好地抑制烟草花叶病毒(TMV)和黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，水稻稻瘟，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌。

  公开号：

  CN113040151A
• 作为产物：
  描述：

  吲哚 、 苯二甲酰亚氨基乙醛 在 碘 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以96%的产率得到2-(2,2-di(1H-indol-3-yl)ethyl)isoindoline-1,3-dione
  参考文献：
  名称：

  生物碱streptindole衍生物及其制备和在防治植物病毒病菌病中的应用

  摘要：

  本发明涉及一种生物碱streptindole衍生物及其制备和在治疗植物病毒病菌病中的应用，本发明首次发现streptindole衍生物I‑1～I‑19表现出很好的抗植物病毒病菌活性，能很好地抑制烟草花叶病毒(TMV)和黄瓜枯萎，花生褐斑，苹果轮纹，小麦纹枯，玉米小斑，西瓜炭疽，水稻恶苗，番茄早疫，小麦赤霉，水稻稻瘟，辣椒疫霉，油菜菌核，黄瓜灰霉，水稻纹枯14种植物病菌。

  公开号：

  CN113045556B

文献信息

• Dry reaction of indoles with carbonyl compounds on montmorillonite K10 clay: a mild, expedient synthesis of diindolylalkanes and vibrindole A
  作者：Manas Chakrabarty、Nandita Ghosh、Ramkrishna Basak、Yoshihiro Harigaya

  DOI：10.1016/s0040-4039(02)00682-2

  日期：2002.5

  Dry reaction of indoles 1a–c with aldehydes 2a–i, ketones 2j–o and an acetal 2p on M. K10 clay at room temperature furnished 3,3′-diindolylalkanes (DIAs: 3a–h, j–r). The novel formation of tris(3-indolyl)methane 4 from 2i through tandem reactions and of the DIAs 6 and 8 from 1d through Plancher rearrangements were also observed.

  在室温下，吲哚1a – c与醛2a – i，酮2j – o和乙缩醛2p在M. K10粘土上的干反应可制得3,3'-二吲哚基烷烃（DIAs：3a – h，j – r）。还观察到了从2i通过串联反应形成的三（3-吲哚基）甲烷4和从1d通过Plancher重排形成的DIAs 6和DIAs 8。
• Short Total Synthesis of (±)-Gelliusine E and 2,3′-Bis(indolyl)ethylamines <i>via</i> PTSA-Catalyzed Transindolylation
  作者：Chayamon Chantana、Uthaiwan Sirion、Panata Iawsipo、Jaray Jaratjaroonphong

  DOI：10.1021/acs.joc.1c01461

  日期：2021.10.1

  A first and short total synthesis of the marine sponge 2,3′-bis(indolyl)ethylamine (2,3′-BIEA) alkaloid (±)-gelliusine E was performed in both a three-step divergent approach and a one-pot three-component approach with an overall yield of up to 58%. A key feature of the novel strategy is PTSA-catalyzed transindolylation of the readily synthesized 3,3′-BIEAs with tryptamine derivatives. The structure

  海绵2,3'-双（吲哚基）乙胺（2,3'-BIEA）生物碱（±）-凝胶E的第一次和短时间全合成以三步发散法和一锅法进行三组分方法，总收率高达 58%。新策略的一个关键特征是容易合成的 3,3'-BIEA 与色胺衍生物的 PTSA 催化转吲哚基化反应。分离的天然产物的结构被修改为质子化 (±)-geliusine E (4')。通过设计，这种模块化路线允许快速合成 2,3'-BIEA 家族的其他成员，例如 (±)-6,6'-双-(debromo)-geliusine F 和具有逐步经济性、可操作性的类似物简单，减少浪费。此外，研究了它们在乳腺癌细胞中的细胞毒性。
• 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、
• Streptindole and Its Derivatives as Novel Antiviral and Anti-Phytopathogenic Fungus Agents
  作者：Jin Kang、Yongyue Gao、Mingjun Zhang、Xin Ding、Ziwen Wang、Dejun Ma、Qingmin Wang

  DOI：10.1021/acs.jafc.0c03994

  日期：2020.7.29

  Plant diseases caused by plant viruses and pathogens seriously affect the production and storage of food crops. With the emergence of drug resistance, it is very difficult to control. Natural products are the source of new drug discovery. Here, the natural product streptindole was found to have good antiviral activity against tobacco mosaic virus (TMV) and fungicidal activities against 14 kinds of phytopathogenic fungi. A series of derivatives of streptindole were designed, synthesized, and evaluated for their antiviral and fungicidal activities. Compounds 4, 5, 11, 12c, 12d, 13d, and 13i-13l showed higher anti-TMV activities than ribavirin (inhibitory rate: 38, 37, and 40% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively), among which compound 12d (inhibitory rate: 57, 55, and 53% at 500 mu g/mL for inactivation, curative, and protection activity in vivo, respectively) with excellent antiviral activity was further evaluated for the mode of action. The mechanism research revealed that 12d can break the three-dimensional structure of TMV coat protein (CP) through hydrogen bonds, thus inhibiting the assembly of virus particles. The molecular docking result showed that compound 12d did exhibit strong interaction with TMV CP. The derivatives of streptindole also displayed broad-spectrum fungicidal activities. The current study provided valuable insights into the antiviral and fungicidal activities of streptindole derivatives.
• A Facile and Efficient Synthesis of 2,2‐Bis(3′/2′‐indolyl)ethylamines and Three Bisindolic Natural Products
  作者：Manas Chakrabarty、Nandita Ghosh、Ramkrishna Basak、Yoshihiro Harigaya

  DOI：10.1081/scc-120027281

  日期：2004.12.31

  A simple and efficient synthesis of bis(indolyl)ethylamines and three bisindolic natural products, viz. hallucinogenic 6, genotoxic 7 and the alkanoic acid 8 has been developed by the reaction of indoles with appropriate carbonyl compounds on montmorillonite K10 clay.