7'-(1H-imidazol-2-yl)-6'-(1H-indole-3-carbonyl)-5-nitro-2-oxo-3',6',7',7a'-tetrahydro-1'H-spiro[indoline-3,5'-pyrrolo[1,2-c]thiazole]-6'-carbonitrile

• 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: 7'-(1H-imidazol-2-yl)-6'-(1H-indole-3-carbonyl)-5-nitro-2-oxo-3',6',7',7a'-tetrahydro-1'H-spiro[indoline-3,5'-pyrrolo[1,2-c]thiazole]-6'-carbonitrile
• 化学式: C₂₆H₁₉N₇O₄S
• 分子量: 525.547
• InChiKey: XSENNIPFZXSMGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.51
• 重原子数：
  38.0
• 可旋转键数：
  4.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  160.81
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  5-硝基靛红 、 3-(1H-imidazol-2-yl)-2-(1H-indole-3-carbonyl)acrylonitrile 、 噻莫西酸 以 乙醇 为溶剂， 反应 2.0h， 以83%的产率得到7'-(1H-imidazol-2-yl)-6'-(1H-indole-3-carbonyl)-5-nitro-2-oxo-3',6',7',7a'-tetrahydro-1'H-spiro[indoline-3,5'-pyrrolo[1,2-c]thiazole]-6'-carbonitrile
  参考文献：
  名称：

  Novel spirooxindole–pyrrolidine compounds: Synthesis, anticancer and molecular docking studies

  摘要：

  Novel spirooxindole pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-y1)-2-(1H-indole-3-carbonypacrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 mu g/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.027

文献信息

• Novel spirooxindole–pyrrolidine compounds: Synthesis, anticancer and molecular docking studies
  作者：Y. Arun、K. Saranraj、C. Balachandran、P.T. Perumal

  DOI：10.1016/j.ejmech.2013.12.027

  日期：2014.3

  Novel spirooxindole pyrrolidine compounds have been synthesised through 1,3-dipolar cycloaddition of azomethine ylides generated from isatin and sarcosine or thioproline with the dipolarophile 3-(1H-imidazol-2-y1)-2-(1H-indole-3-carbonypacrylonitrile under the optimised reaction condition. Synthesised compounds were evaluated for their anticancer activity against A549 human lung adenocarcinoma cancer cell line. Among the 29 tested compounds 4j, 6b and 6h showed very high activity 66.3%, 64.8% and 66.3% at 25 mu g/mL concentration against A549 lung adenocarcinoma cancer cell line. These spirooxindole pyrrolidine compounds can be promising therapeutic agents for A549 lung adenocarcinoma cancer cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.