4′-(thiophen-2-yl)-[2,3′-bifuran]-2′,5′-dione | 237079-31-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: 4′-(thiophen-2-yl)-[2,3′-bifuran]-2′,5′-dione
• 英文别名: 3-(Furan-2-yl)-4-thiophen-2-ylfuran-2,5-dione
• CAS: 237079-31-1
• 化学式: C₁₂H₆O₄S
• 分子量: 246.243
• InChiKey: BREMKPAZZHDGLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  84.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4′-(thiophen-2-yl)-[2,3′-bifuran]-2′,5′-dione 在 碘 作用下， 以 丙酮 为溶剂， 反应 13.0h， 以86%的产率得到furo[3,4-g]thieno[3,2-e]benzofuran-7,9-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 3.17h， 生成 4′-(thiophen-2-yl)-[2,3′-bifuran]-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

• Facile Synthesis of γ-Butenolides and Maleic Anhydrides via Annulation of α-Keto Acids and Triazenyl Alkynes
  作者：Xiaodong Bao、Linwei Zeng、Jian Jin、Sunliang Cui

  DOI：10.1021/acs.joc.1c02727

  日期：2022.3.4

  A facile synthesis of γ-butenolides and maleic anhydrides via annulation of α-keto acids and triazenyl alkynes is described. In this process, α-keto acids and triazenyl alkynes could undergo a self-catalyzed annulation at room temperature to deliver γ-butenolides efficiently, while the further addition of BF3–Et2O furnished maleic anhydrides. Overall, these processes have mild reaction conditions,

  描述了通过 α-酮酸和三氮烯基炔烃的环化轻松合成 γ-丁烯内酯和马来酸酐。在这个过程中，α-酮酸和三氮烯基炔烃可以在室温下进行自催化环化以有效地提供γ-丁烯内酯，而进一步添加BF 3 -Et 2 O 则提供马来酸酐。总体而言，这些工艺反应条件温和、适用范围广、效率高。
• Synthesis, structural, and biological evaluation of bis-heteroarylmaleimides and bis-heterofused imides
  作者：Nicola Ferri、Tiziano Radice、Manuela Antonino、Egle Maria Beccalli、Stella Tinelli、Franco Zunino、Alberto Corsini、Graziella Pratesi、Enzio M. Ragg、Maria Luisa Gelmi、Alessandro Contini

  DOI：10.1016/j.bmc.2011.08.016

  日期：2011.9

  Bis-2,3-heteroarylmaleimides and polyheterocondensed imides joined through nitrogen atoms of the N, N'-bis(ethyl)-1,3-propanediamine linker were prepared from substituted maleic anhydrides and symmetrical diamines in good to satisfactory yields and short reaction times using microwave heating. The novel molecules were shown to inhibit proliferation of human tumor cells (NCI-H460 lung carcinoma) and rat aortic smooth muscle cells (SMCs) with variable potencies. Compound 11a, the most potent one of the series, showed IC50 values comparable to those observed for the leading molecule elinafide in both cell lines, but with a higher selectivity toward human tumor cells. Compound 11a affected G1/S phase transition of the cell cycle, showed in vitro DNA intercalating activity and in vivo antitumor activity. A thorough structural analysis of the 11a-DNA complex was also made by mean of NMR and computational techniques. (C) 2011 Elsevier Ltd. All rights reserved.
• 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.