1'-(prop-2-ynyl)-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione | 1376662-52-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1'-(prop-2-ynyl)-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione
• 英文别名: 1'-Prop-2-ynylspiro[15-azatetracyclo[8.6.0.03,8.011,15]hexadeca-1(10),3,5,7-tetraene-16,3'-indole]-2,2',9-trione
• CAS: 1376662-52-0
• 化学式: C₂₅H₁₈N₂O₃
• 分子量: 394.43
• InChiKey: IGGCWCXLHMSCSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  30
• 可旋转键数：
  1
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  57.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-(2-丙炔)-1H-吲哚-2,3-二酮 、 L-脯氨酸 、 1,4-萘醌 在 air 作用下， 以 乙醇 为溶剂， 反应 1.5h， 以93%的产率得到1'-(prop-2-ynyl)-1,2,3,11b-tetrahydrospiro[benzo[f]pyrrolo[2,1-a]isoindole-5,3'-indoline]-2',6,11-trione
  参考文献：
  名称：

  Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity

  摘要：

  A series of novel spirooxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine or L-proline with the dipolarophile 1,4-naphthoquinone followed by spontaneous dehydrogenation. Synthesised compounds were evaluated for their antimicrobial activities against eight bacteria and three fungi. All the spirooxindole derivatives exhibited significant antibacterial activity against Staphylococcus aureus, S. aureus (MRSA), Enterobacter aerogens, Micrococcus luteus, Proteus vulgaris, Klebsiella pneumonia, Salmonella typhimurium, Salmonella paratyphi-B and anti-fungal activity against Malassesia pachydermatis, Candida albicans and Botyritis cinerea organisms. Among 23 compounds screened, 1'-acetyl-2,5'-dimethyl-2,3-dihydrospiro[benzo[f] isoindole-1,3'-indoline]-2',4,9-trione was found to be more active against tested bacteria and fungi. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.02.024

文献信息

• Synthesis of novel spirooxindole derivatives by one pot multicomponent reaction and their antimicrobial activity
  作者：Gangaru Bhaskar、Yuvaraj Arun、Chandrasekar Balachandran、Chandrasekara Saikumar、Paramasivan T. Perumal

  DOI：10.1016/j.ejmech.2012.02.024

  日期：2012.5

  A series of novel spirooxindoles have been synthesized through 1,3-dipolar cycloaddition of an azomethine ylide generated from isatin and sarcosine or L-proline with the dipolarophile 1,4-naphthoquinone followed by spontaneous dehydrogenation. Synthesised compounds were evaluated for their antimicrobial activities against eight bacteria and three fungi. All the spirooxindole derivatives exhibited significant antibacterial activity against Staphylococcus aureus, S. aureus (MRSA), Enterobacter aerogens, Micrococcus luteus, Proteus vulgaris, Klebsiella pneumonia, Salmonella typhimurium, Salmonella paratyphi-B and anti-fungal activity against Malassesia pachydermatis, Candida albicans and Botyritis cinerea organisms. Among 23 compounds screened, 1'-acetyl-2,5'-dimethyl-2,3-dihydrospiro[benzo[f] isoindole-1,3'-indoline]-2',4,9-trione was found to be more active against tested bacteria and fungi. (C) 2012 Elsevier Masson SAS. All rights reserved.