5-chloro-1,2-dihydro-5'H-spiro[indole-3,4'-pyrrolo[1,2-a]-quinoxaline]-2-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-chloro-1,2-dihydro-5'H-spiro[indole-3,4'-pyrrolo[1,2-a]-quinoxaline]-2-one
• 英文别名: 5-chloro-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one；5-chlorospiro[1H-indole-3,4'-5H-pyrrolo[1,2-a]quinoxaline]-2-one
• 化学式: C₁₈H₁₂ClN₃O
• 分子量: 321.766
• InChiKey: NFUMKRJBKROCNJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  23
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1-(2-氨基苯基)吡咯 、 5-氯靛红 在 Amberlite IR-120H resin 作用下， 以 水 为溶剂， 反应 2.5h， 以95%的产率得到5-chloro-1,2-dihydro-5'H-spiro[indole-3,4'-pyrrolo[1,2-a]-quinoxaline]-2-one
  参考文献：
  名称：

  Amberlite IR-120H：一种高效且可回收的多相催化剂，用于合成吡咯并[1,2- a ]喹喔啉和5'H-螺[吲哚啉-3,4'-吡咯并[1,2- a ]喹喔啉] -2 -那些

  摘要：

  已开发了一种绿色环保且可回收的催化剂Amberlite IR-120H树脂，在无溶剂条件下合成吡咯并[1,2- a ]喹喔啉的简单，高效且环境友好的方法。该方法具有许多优点，例如温和的条件，不使用氧化剂，环境相容和廉价的催化剂。而且，催化剂可以在反应完成后回收，并且可以使用，因为即使在五个循环内树脂的催化性能也不会受到影响。

  DOI：

  10.1016/j.tetlet.2015.11.003

文献信息

• Amberlite IR-120H: an efficient and recyclable heterogeneous catalyst for the synthesis of pyrrolo[1,2-a]quinoxalines and 5′H-spiro[indoline-3,4′-pyrrolo[1,2-a]quinoxalin]-2-ones
  作者：Ahmed Kamal、Korrapati Suresh Babu、Jeshma Kovvuri、Vindravath Manasa、A. Ravikumar、Abdullah Alarifi

  DOI：10.1016/j.tetlet.2015.11.003

  日期：2015.12

  A simple, highly efficient and environmentally benign method for the synthesis of pyrrolo[1,2-a]quinoxalines has been developed using a green and recyclable catalyst Amberlite IR-120H resin under solvent-free conditions. The method provides several advantages such as mild conditions, no use of oxidant, environmentally compatible and inexpensive catalyst. Moreover, the catalyst can be recovered after

  已开发了一种绿色环保且可回收的催化剂Amberlite IR-120H树脂，在无溶剂条件下合成吡咯并[1,2- a ]喹喔啉的简单，高效且环境友好的方法。该方法具有许多优点，例如温和的条件，不使用氧化剂，环境相容和廉价的催化剂。而且，催化剂可以在反应完成后回收，并且可以使用，因为即使在五个循环内树脂的催化性能也不会受到影响。
• An eco-friendly Pictet–Spengler approach to pyrrolo- and indolo[1,2-a]quinoxalines using p-dodecylbenzenesulfonic acid as an efficient Brønsted acid catalyst
  作者：Amreeta Preetam、Mahendra Nath

  DOI：10.1039/c4ra16651e

  日期：——

  facile and environmentally benign Pictet–Spengler strategy for the synthesis of a series of biologically important pyrrolo- and indolo[1,2-a]quinoxalines has been developed by reacting 1-(2-aminophenyl)-pyrrole or 1-(2-aminophenyl)indoles with a wide range of aromatic aldehydes, acetophenones or isatins in ethanol at ambient temperature using p-dodecylbenzenesulfonic acid (p-DBSA) as an efficient Brønsted

  一种简便和对环境无害的Pictet-格勒策略一系列生物学上重要的吡咯和的合成吲哚并[1,2一]喹喔啉已经通过使1-（2-氨基苯基） -吡咯或1-显影（2-使用对十二烷基苯磺酸（p -DBSA）作为有效的布朗斯台德酸-表面活性剂联合催化剂，在环境温度下，在乙醇中可与多种芳香族醛，苯乙酮或靛红类的吲哚苯并吲哚混合。发现该方法适用于在温和的反应条件下以相当好的收率产生各种喹喔啉衍生物。
• Discovery of pyrrolospirooxindole derivatives as novel cyclin dependent kinase 4 (CDK4) inhibitors by catalyst-free, green approach
  作者：Ahmed Kamal、Rasala Mahesh、V. Lakshma Nayak、Korrapati Suresh Babu、G. Bharath Kumar、Anver Basha Shaik、Jeevak Sopanrao Kapure、Abdullah Alarifi

  DOI：10.1016/j.ejmech.2015.11.046

  日期：2016.1

  Aiming to develop a new target for the anticancer treatment, a series of 5'H-spiro[indoline-3,4'-pyrrolo [1,2-a]quinoxalin]-2-ones has been synthesized by simple, highly efficient and environmentally friendly method in excellent yields under catalyst-free conditions using ethanol as a green solvent. A simple filtration of the reaction mixture and subsequent drying affords analytically pure products. The synthesized derivatives were evaluated for their antiproliferative activity against five different human cancer cell lines, among the congeners compound 3n showed significant cytotoxicity against the human prostate cancer (DU-145). Flow cytometric analysis revealed that this compound induces cell cycle arrest in the G0/G1 phase and Western blot analysis suggested that reduction in Cdk4 expression level leads to apoptotic cell death. This was further confirmed by mitochondrial membrane potential ((Delta Psi m), Annexin V-FITC assay and docking experiments. Furthermore, it was observed that there is an increase in expression levels of cyclin dependent kinase inhibitors like Cip1/p21 and Kip1/p27. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis of novel 4,5‐dihydropyrrolo[1,2‐ <i>a</i> ]quinoxalines, pyrrolo[1,2‐ <i>a</i> ]quinoxalin]‐2‐ones and their antituberculosis and anticancer activity
  作者：Vitthal B. Makane、Eruva Vamshi Krishna、Uattam B. Karale、Dattatraya A. Babar、Saradhi Kalari、Estharla M. Rekha、Manjulika Shukla、Grace Kaul、Dharmarajan Sriram、Sidharth Chopra、Sunil Misra、Haridas B. Rode

  DOI：10.1002/ardp.202000192

  日期：2020.12

  A facile strategy was developed for the synthesis of biologically important 4,5‐dihydropyrrolo[1,2‐a]quinoxalines and pyrrolo[1,2‐a]quinoxalin]‐2‐ones by treating 2‐(1H‐pyrrol‐1‐yl)anilines with imidazo[1,2‐a]pyridine‐3‐carbaldehyde or isatin, using amidosulfonic acid (NH3SO3) as a solid catalyst in water at room temperature. The protocol has been extended to electrophile ninhydrin. The catalyst could

  通过处理 2-(1H-pyrrol-1-基）苯胺与咪唑并[1,2-a]吡啶-3-甲醛或靛红，在室温下使用酰胺磺酸（NH3SO3）作为固体催化剂在水中。该协议已扩展到亲电茚三酮。催化剂可循环使用六次而不会损失活性。评估了这些化合物的抗结核、抗菌和抗癌活性。值得注意的是，化合物 3d 和 3e 对结核分枝杆菌 H37Rv 的最小抑制浓度值为 6.25 µM，而化合物 3d、3g、5d、5e 和 5i 对 A549、DU145、HeLa、HepG2、MCF- 7 和 B16-F10 细胞系，分别。