1-methyl-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione

• 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-methyl-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione
• 英文别名: 1-methyl-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)dione；1-methyl-3'-(4-methylphenyl)-1'H-spiro[indole-3,2'-quinazoline]-2,4'(1H,3'H)-dione；1'-methyl-3-(4-methylphenyl)spiro[1H-quinazoline-2,3'-indole]-2',4-dione
• 化学式: C₂₃H₁₉N₃O₂
• 分子量: 369.423
• InChiKey: KKBTUMGWFOSEOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  靛红 在 caesium carbonate 作用下， 以 溶剂黄146 、 乙腈 为溶剂， 反应 7.5h， 生成 1-methyl-3'-(p-tolyl)-1'H-spiro[indoline-3,2'-quinazoline]-2,4'(3'H)-dione
  参考文献：
  名称：

  Microwave Heated Flow Synthesis of Spiro-oxindole Dihydroquinazolinone Based IRAP Inhibitors

  摘要：

  A fast and convenient synthetic route towards spiro-oxindole dihydroquinazolinones as novel and drug-like insulin-regulated aminopeptidase (IRAP) inhibitors is reported. The synthesis is performed using a MW heated continuous flow system employing 200 mm X 3 mm i MW absorbing silicon carbide (SiC) or MW transparent borosilicate tubular reactors. A three-component MW-flow reaction to build up the spiro compounds (9 examples, 4087% yield), using the SiC reactor, as well as a SuzukiMiyaura cross-coupling reaction (71%), employing the borosilicate reactor, are presented with residence times down to 168 s. The continuous MW-flow routes provide a smooth and scalable synthetic methodology towards this class of IRAP inhibitors.

  DOI：

  10.1021/op500237k

文献信息

• Design, synthesis and docking studies of some spiro-oxindole dihydroquinazolinones as antibacterial agents
  作者：Jin Zhang、Jiawen Zhao、Liangpeng Wang、Jia Liu、Decheng Ren、Yangmin Ma

  DOI：10.1016/j.tet.2015.12.055

  日期：2016.2

  Two series of spiro-oxindole dihydroquinazolinone derivatives have been designed and synthesized using a catalytic amount of nano cerium oxide with excellent product yields by a convenient one-pot process. The synthesized compounds were evaluated for their in vitro antibacterial activity, and compounds 1i-1p showed considerable antibacterial activities to Escherichia coli. Molecular docking of E. coli Biotin Carboxylase (EcBC) enzyme was also performed in order to predict the interactions of the synthesized compounds. (C) 2016 Published by Elsevier Ltd.
• Microwave Heated Flow Synthesis of Spiro-oxindole Dihydroquinazolinone Based IRAP Inhibitors
  作者：Karin Engen、Jonas Sävmarker、Ulrika Rosenström、Johan Wannberg、Thomas Lundbäck、Annika Jenmalm-Jensen、Mats Larhed

  DOI：10.1021/op500237k

  日期：2014.11.21

  A fast and convenient synthetic route towards spiro-oxindole dihydroquinazolinones as novel and drug-like insulin-regulated aminopeptidase (IRAP) inhibitors is reported. The synthesis is performed using a MW heated continuous flow system employing 200 mm X 3 mm i MW absorbing silicon carbide (SiC) or MW transparent borosilicate tubular reactors. A three-component MW-flow reaction to build up the spiro compounds (9 examples, 4087% yield), using the SiC reactor, as well as a SuzukiMiyaura cross-coupling reaction (71%), employing the borosilicate reactor, are presented with residence times down to 168 s. The continuous MW-flow routes provide a smooth and scalable synthetic methodology towards this class of IRAP inhibitors.