ethyl 5-amino-3-(4-trifluoromethylbenzoylamino)benzo[b]thiophene-2-carboxylate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: ethyl 5-amino-3-(4-trifluoromethylbenzoylamino)benzo[b]thiophene-2-carboxylate
• 英文别名: Ethyl 5-amino-3-[[4-(trifluoromethyl)benzoyl]amino]-1-benzothiophene-2-carboxylate；ethyl 5-amino-3-[[4-(trifluoromethyl)benzoyl]amino]-1-benzothiophene-2-carboxylate
• 化学式: C₁₉H₁₅F₃N₂O₃S
• 分子量: 408.401
• InChiKey: ABDQHVCFTWOBQO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ethyl 5-amino-3-(4-trifluoromethylbenzoylamino)benzo[b]thiophene-2-carboxylate 在 sodium cyanoborohydride 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 ethyl 5-[(5-methyl-1H-imidazol-4-ylmethyl)amino]-3-(4-trifluoromethylbenzoylamino)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[b]thiophene derivatives

  摘要：

  A new series of 3-benzoylamino-5-imidazol-5-yl-benzo[b]thiophenes and the parent amino derivatives were synthesized and screened as antitumor agents. All tested compounds showed concentration-dependent antiproliferative activity profile against HeLa cell line, exhibiting GI50 values in the low micromolar range. The most active compounds were tested in cell cycle perturbation experiments. A rapid accumulation of cells in the G2/M phase, with a concomitant reduction of cells in both the S and G0/G1 phases, was observed, suggesting that cell exposure to selected derivatives produces mitotic failure. To rationalize the biological results, the 3-benzoylamino-benzo[b]thiophenes were analyzed through the in silk VLAK protocol. Compounds presenting the 3,4,5-trimethoxy-benzoyl moiety were in silica classified as potential antimitotic agents or topoisomerase II inhibitors, in good agreement with the biological studies. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.002
• 作为产物：
  描述：

  ethyl (3-amino-5-nitrobenzothiophen)-2-carboxylate 在 吡啶 、 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、3.45 MPa 条件下， 反应 14.0h， 生成 ethyl 5-amino-3-(4-trifluoromethylbenzoylamino)benzo[b]thiophene-2-carboxylate
  参考文献：
  名称：

  Synthesis, antiproliferative activity, and in silico insights of new 3-benzoylamino-benzo[b]thiophene derivatives

  摘要：

  A new series of 3-benzoylamino-5-imidazol-5-yl-benzo[b]thiophenes and the parent amino derivatives were synthesized and screened as antitumor agents. All tested compounds showed concentration-dependent antiproliferative activity profile against HeLa cell line, exhibiting GI50 values in the low micromolar range. The most active compounds were tested in cell cycle perturbation experiments. A rapid accumulation of cells in the G2/M phase, with a concomitant reduction of cells in both the S and G0/G1 phases, was observed, suggesting that cell exposure to selected derivatives produces mitotic failure. To rationalize the biological results, the 3-benzoylamino-benzo[b]thiophenes were analyzed through the in silk VLAK protocol. Compounds presenting the 3,4,5-trimethoxy-benzoyl moiety were in silica classified as potential antimitotic agents or topoisomerase II inhibitors, in good agreement with the biological studies. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.12.002