diethyl benzo[1,2-b:4,3-b']dithiophene-4,5-dicarboxylate | 1020413-15-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: diethyl benzo[1,2-b:4,3-b']dithiophene-4,5-dicarboxylate
• 英文别名: Diethyl thieno[3,2-e][1]benzothiophene-4,5-dicarboxylate；diethyl thieno[3,2-e][1]benzothiole-4,5-dicarboxylate
• CAS: 1020413-15-3
• 化学式: C₁₆H₁₄O₄S₂
• 分子量: 334.417
• InChiKey: JWRCSWNJWBIEDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diethyl benzo[1,2-b:4,3-b']dithiophene-4,5-dicarboxylate 、 N,N-二乙基乙二胺 反应 12.0h， 以28%的产率得到14-[2-(Diethylamino)ethyl]-3,10-dithia-14-azatetracyclo[10.3.0.02,6.07,11]pentadeca-1,4,6,8,11-pentaene-13,15-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：

  diethyl 2,3-di(thiophen-2-yl)but-2-enedioate 在 碘 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 8.0h， 以54%的产率得到diethyl benzo[1,2-b:4,3-b']dithiophene-4,5-dicarboxylate
  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