ethyl 2-(thiophene-2-carbonyl)-3-trifluoromethylquinoxaline-7-carboxylate 1,4-di-N-oxide | 1339191-98-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: ethyl 2-(thiophene-2-carbonyl)-3-trifluoromethylquinoxaline-7-carboxylate 1,4-di-N-oxide
• 英文别名: Ethyl 1-oxido-4-oxo-3-(thiophene-2-carbonyl)-2-(trifluoromethyl)quinoxalin-4-ium-6-carboxylate；ethyl 1-oxido-4-oxo-3-(thiophene-2-carbonyl)-2-(trifluoromethyl)quinoxalin-4-ium-6-carboxylate
• CAS: 1339191-98-8
• 化学式: C₁₇H₁₁F₃N₂O₅S
• 分子量: 412.346
• InChiKey: ZXANGUQAUJQGHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5(6)-Ethoxycarbonyl-benzofuroxan 、 2-噻吩甲酰三氟丙酮 在 三乙胺 作用下， 以 氯仿 为溶剂， 以23.2%的产率得到ethyl 2-(thiophene-2-carbonyl)-3-trifluoromethylquinoxaline-7-carboxylate 1,4-di-N-oxide
  参考文献：
  名称：

  Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica

  摘要：

  In our search for new antiamoebic agents, a new series of ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives have been synthesized using the Beirut reaction. All compounds were characterized by spectroscopic techniques and elemental analysis. Antiamoebic activity was evaluated in vitro against Entamoeba histolytica strain HM1:IMSS by the microdilution method, and the structure-activity relationship was analyzed. We found that eleven quinoxaline derivatives showed greater activity than metronidazole and nitazoxanide with IC50 values in the range 1.99-0.35 mu M. Compounds T-001 and T-016 shows IC50 values of 1.41 and 1.47 mu M, respectively, with a value of selectivity index >60. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.036

文献信息

• Synthesis and in vitro evaluation of new ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide against Entamoeba histolytica
  作者：Blanca Estela Duque-Montaño、Lilia Citlalli Gómez-Caro、Mario Sanchez-Sanchez、Antonio Monge、Efrén Hernández-Baltazar、Gildardo Rivera、Oscar Torres-Angeles

  DOI：10.1016/j.bmc.2013.05.036

  日期：2013.8

  In our search for new antiamoebic agents, a new series of ethyl and methyl quinoxaline-7-carboxylate 1,4-di-N-oxide derivatives have been synthesized using the Beirut reaction. All compounds were characterized by spectroscopic techniques and elemental analysis. Antiamoebic activity was evaluated in vitro against Entamoeba histolytica strain HM1:IMSS by the microdilution method, and the structure-activity relationship was analyzed. We found that eleven quinoxaline derivatives showed greater activity than metronidazole and nitazoxanide with IC50 values in the range 1.99-0.35 mu M. Compounds T-001 and T-016 shows IC50 values of 1.41 and 1.47 mu M, respectively, with a value of selectivity index >60. (C) 2013 Elsevier Ltd. All rights reserved.