1-benzyl-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one | 1443437-34-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-benzyl-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
• 英文别名: 1'-benzylspiro[5H-pyrrolo[1,2-a]quinoxaline-4,3'-indole]-2'-one
• CAS: 1443437-34-0
• 化学式: C₂₅H₁₉N₃O
• 分子量: 377.445
• InChiKey: PYTBVOHTYWWGMY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N'-(1-benzyl-2-oxoindolin-3-ylidene)-4-methylbenzenesulfonohydrazide 、 1-(2-氨基苯基)吡咯 在 copper (II) carbonate hydroxide 、 silver hexafluoroantimonate 、 sodium hydroxide 作用下， 以 乙腈 为溶剂， 反应 41.0h， 以46%的产率得到1-benzyl-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
  参考文献：
  名称：

  铜催化邻吡咯苯胺和杂环 N-甲苯磺酰腙的 [5 + 1] 环化制备螺二氢吡咯并[1,2-a]喹喔啉衍生物

  摘要：

  已经描述了一种廉价的铜催化顺序反应过程，该过程通过胺亲核攻击从杂环N-甲苯磺酰腙前体原位产生的 Cu-卡宾，然后是N-叶立德的 1,2-H 位移/氧化环化级联。，顺利生成相应的结构上各种螺二氢吡咯并[1,2- a ]喹喔啉衍生物。此外, 该协议的重要性还可以通过其将合成化合物多种转化为潜在的生物活性分子 (如 2-取代的 pyrrolo[1,2- a ] 喹喔啉) 来突出。

  DOI：

  10.1021/acs.joc.1c02909

文献信息

• 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。
• 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 spiro[indoline-3,4′-pyrrolo[1,2-a]quinoxalin]-2-one catalyzed by molecular iodine
  作者：Abdolali Alizadeh、Javad Mokhtari

  DOI：10.1016/j.tet.2013.03.102

  日期：2013.7

  Molecular iodine catalyzed preparation of spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one. This reaction between N-(2-aminophenyl)pyrrole and isatins proceeds in CH3CN at room temperature in good to excellent yields. (C) 2013 Elsevier Ltd. All rights reserved.