1-benzyl-5-bromo-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one | 1443437-35-1

• 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-bromo-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
• 英文别名: 1'-benzyl-5'-bromospiro[5H-pyrrolo[1,2-a]quinoxaline-4,3'-indole]-2'-one
• CAS: 1443437-35-1
• 化学式: C₂₅H₁₈BrN₃O
• 分子量: 456.341
• InChiKey: ZKCSGEPCVQUGGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 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：

  1-(2-氨基苯基)吡咯 、 5-溴-1-(苯基甲基)吲哚-2,3-二酮 以 乙醇 为溶剂， 反应 11.0h， 以95%的产率得到1-benzyl-5-bromo-5'H-spiro[indoline-3,4'-pyrrolo[1,2-a]quinoxalin]-2-one
  参考文献：
  名称：

  Discovery of pyrrolospirooxindole derivatives as novel cyclin dependent kinase 4 (CDK4) inhibitors by catalyst-free, green approach

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.11.046

文献信息

• 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.