diethyl 6-methyl-6H-thieno[3,2-e]-indole-4,5-dicarboxylate | 1020413-14-2

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: diethyl 6-methyl-6H-thieno[3,2-e]-indole-4,5-dicarboxylate
• CAS: 1020413-14-2
• 化学式: C₁₇H₁₇NO₄S
• 分子量: 331.392
• InChiKey: RHINZZIHEUYYIO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.75
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  57.53
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  diethyl 6-methyl-6H-thieno[3,2-e]-indole-4,5-dicarboxylate 在 sodium hydroxide 、 对甲苯磺酸 作用下， 以 乙醇 、 水 、 二氯甲烷 为溶剂， 反应 8.5h， 以86%的产率得到6-methyl-6H-furo[3,4-g]thieno[3,2-e]indole-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：

  diethyl 2-(N-methyl-1H-pyrrol-2-yl)-3-(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52%的产率得到diethyl 6-methyl-6H-thieno[3,2-e]-indole-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