3-(1H-Indol-2-yl)-4-thiophen-2-yl-furan-2,5-dione | 62787-08-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 3-(1H-Indol-2-yl)-4-thiophen-2-yl-furan-2,5-dione
• 英文别名: 2,5-Furandione, 3-(1H-indol-2-yl)-4-(2-thienyl)-；3-(1H-indol-2-yl)-4-thiophen-2-ylfuran-2,5-dione
• CAS: 62787-08-0
• 化学式: C₁₆H₉NO₃S
• 分子量: 295.318
• InChiKey: STUAPTCNNYAPSM-UHFFFAOYSA-N

物化性质

• 沸点：
  574.9±50.0 °C(Predicted)
• 密度：
  1.535±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  87.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N,N-二乙基乙二胺 、 3-(1H-Indol-2-yl)-4-thiophen-2-yl-furan-2,5-dione 以 二氯甲烷 为溶剂， 反应 0.25h， 以100%的产率得到1-[2-(diethylamino)ethyl]-3-(1H-indol-2-yl)-4-thiophen-2-ylpyrrole-2,5-dione
  参考文献：
  名称：

  Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides

  摘要：

  A series of 2,3-heteroarylmaleimides 9 and polyheterocondensed imides 12 were prepared in good yields and short reaction time using a very efficient procedure consisting in the condensation of the corresponding anhydrides and N,N-diethylethylenediamine and microwave heating. The antiproliferative activity of the novel molecules was tested against human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs). The IC50 values for the novel molecules ranged from 0.08 to 13.9 mu M in SMCs, and from 0.84 to 9 mu M in the tumor cell line. The activity pro. le for compounds 9 and 12 is comparable to that obtained for amonafide in NCI-H460, except for fused imides 12b,i which proved to be about 10-fold more potent. Whereas, in rat SMCs, only the compound 12b was shown to be 10-fold more potent than amonafide. Instead 12c is equipotent to amonafide. These results suggest that the extended pi-system and the kind of heteroatom are essential in the binding with the molecular target. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.024
• 作为产物：
  描述：

  2-噻吩乙酸乙酯 在 sodium hydroxide 、 copper(l) iodide 、 四(三苯基膦)钯 、 水 、 sodium ethanolate 、 N,N-二异丙基乙胺 、 lithium chloride 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.67h， 生成 3-(1H-Indol-2-yl)-4-thiophen-2-yl-furan-2,5-dione
  参考文献：
  名称：

  A New Access to Diarylmaleic Anhydrides

  摘要：

  A new three-step synthesis of diarylmaleic anhydrides 6, starting from 3-aryl-2-hydroxybut-2-enedioates 2, is reported.

  DOI：

  10.1002/(sici)1099-0690(199906)1999:6<1421::aid-ejoc1421>3.0.co;2-o

文献信息

• A New Access to Diarylmaleic Anhydrides
  作者：Egle M. Beccalli、Maria Luisa Gelmi、Alessandro Marchesini

  DOI：10.1002/(sici)1099-0690(199906)1999:6<1421::aid-ejoc1421>3.0.co;2-o

  日期：1999.6

  A new three-step synthesis of diarylmaleic anhydrides 6, starting from 3-aryl-2-hydroxybut-2-enedioates 2, is reported.
• Antiproliferative effects on human tumor cells and rat aortic smooth muscular cells of 2,3-heteroarylmaleimides and heterofused imides
  作者：Nicola Ferri、Egle Maria Beccalli、Alessandro Contini、Alberto Corsini、Manuela Antonino、Tiziano Radice、Graziella Pratesi、Stella Tinelli、Franco Zunino、Maria Luisa Gelmi

  DOI：10.1016/j.bmc.2007.11.024

  日期：2008.2.15

  A series of 2,3-heteroarylmaleimides 9 and polyheterocondensed imides 12 were prepared in good yields and short reaction time using a very efficient procedure consisting in the condensation of the corresponding anhydrides and N,N-diethylethylenediamine and microwave heating. The antiproliferative activity of the novel molecules was tested against human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs). The IC50 values for the novel molecules ranged from 0.08 to 13.9 mu M in SMCs, and from 0.84 to 9 mu M in the tumor cell line. The activity pro. le for compounds 9 and 12 is comparable to that obtained for amonafide in NCI-H460, except for fused imides 12b,i which proved to be about 10-fold more potent. Whereas, in rat SMCs, only the compound 12b was shown to be 10-fold more potent than amonafide. Instead 12c is equipotent to amonafide. These results suggest that the extended pi-system and the kind of heteroatom are essential in the binding with the molecular target. (C) 2007 Elsevier Ltd. All rights reserved.