Furan-2-yl-[4-oxido-1-oxo-3,6-bis(trifluoromethyl)quinoxalin-1-ium-2-yl]methanone | 957785-63-6

• 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: Furan-2-yl-[4-oxido-1-oxo-3,6-bis(trifluoromethyl)quinoxalin-1-ium-2-yl]methanone
• CAS: 957785-63-6
• 化学式: C₁₅H₆F₆N₂O₄
• 分子量: 392.214
• InChiKey: DGBWTDCILDELEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  76.6
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Furan-2-yl-[4-oxido-1-oxo-3,6-bis(trifluoromethyl)quinoxalin-1-ium-2-yl]methanone 以 甲醇 、 水 为溶剂， 以45%的产率得到Furan-2-yl-(1-oxy-3,6-bis-trifluoromethyl-quinoxalin-2-yl)-methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 2-Arylcarbonyl-3-trifluoromethylquinoxaline 1,4-Di-N-oxide Derivatives and Their Reduced Analogues

  摘要：

  As a continuation of our research in the quinoxaline 1,4-di-N-oxide new series of 2-arylearbonyl-3-trifluoromethylquinoxaline, 1,4-di-N-oxide derivatives have been synthesized and evaluated in a full panel of 60 human tumor cell lines. Selective reductions were carried out on two compounds which allowed us to determine the compound structures by comparison of the H-1 NMR spectra. In general, all the di-Noxidized compounds showed good cytotoxic parameters. The best activity was observed in derivatives with electron-withdrawing groups in position 6 or 7 on the quinoxaline ring and in the unsubstituted analogues, whereas loss of one or two oxygens reduced the cytotoxicity. The best five compounds were selected for evaluation for the in vivo hollow fiber assays. In vitro studies reveal that compound 5h efficiently generates reactive oxygen species via redox cycling in the presence of the NADPH/cytochrome P450 enzyme system, providing a plausible molecular mechanism for the observed aerobic cytotoxicity of these quinoxaline N-oxides.

  DOI：

  10.1021/jm0703993
• 作为产物：
  描述：

  4,4,4-三氟-1-(2-呋喃基)-1,3-丁二酮 、 5-trifluoromethylbenzofuroxan 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 Furan-2-yl-[4-oxido-1-oxo-3,7-bis(trifluoromethyl)quinoxalin-1-ium-2-yl]methanone 、 Furan-2-yl-[4-oxido-1-oxo-3,6-bis(trifluoromethyl)quinoxalin-1-ium-2-yl]methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of New 2-Arylcarbonyl-3-trifluoromethylquinoxaline 1,4-Di-N-oxide Derivatives and Their Reduced Analogues

  摘要：

  As a continuation of our research in the quinoxaline 1,4-di-N-oxide new series of 2-arylearbonyl-3-trifluoromethylquinoxaline, 1,4-di-N-oxide derivatives have been synthesized and evaluated in a full panel of 60 human tumor cell lines. Selective reductions were carried out on two compounds which allowed us to determine the compound structures by comparison of the H-1 NMR spectra. In general, all the di-Noxidized compounds showed good cytotoxic parameters. The best activity was observed in derivatives with electron-withdrawing groups in position 6 or 7 on the quinoxaline ring and in the unsubstituted analogues, whereas loss of one or two oxygens reduced the cytotoxicity. The best five compounds were selected for evaluation for the in vivo hollow fiber assays. In vitro studies reveal that compound 5h efficiently generates reactive oxygen species via redox cycling in the presence of the NADPH/cytochrome P450 enzyme system, providing a plausible molecular mechanism for the observed aerobic cytotoxicity of these quinoxaline N-oxides.

  DOI：

  10.1021/jm0703993

文献信息

• Synthesis and Biological Evaluation of New 2-Arylcarbonyl-3-trifluoromethylquinoxaline 1,4-Di-<i>N</i>-oxide Derivatives and Their Reduced Analogues
  作者：Beatriz Solano、Venkatraman Junnotula、Adoración Marín、Raquel Villar、Asunción Burguete、Esther Vicente、Silvia Pérez-Silanes、Ignacio Aldana、Antonio Monge、Sanjay Dutta、Ujjal Sarkar、Kent S. Gates

  DOI：10.1021/jm0703993

  日期：2007.11.1

  As a continuation of our research in the quinoxaline 1,4-di-N-oxide new series of 2-arylearbonyl-3-trifluoromethylquinoxaline, 1,4-di-N-oxide derivatives have been synthesized and evaluated in a full panel of 60 human tumor cell lines. Selective reductions were carried out on two compounds which allowed us to determine the compound structures by comparison of the H-1 NMR spectra. In general, all the di-Noxidized compounds showed good cytotoxic parameters. The best activity was observed in derivatives with electron-withdrawing groups in position 6 or 7 on the quinoxaline ring and in the unsubstituted analogues, whereas loss of one or two oxygens reduced the cytotoxicity. The best five compounds were selected for evaluation for the in vivo hollow fiber assays. In vitro studies reveal that compound 5h efficiently generates reactive oxygen species via redox cycling in the presence of the NADPH/cytochrome P450 enzyme system, providing a plausible molecular mechanism for the observed aerobic cytotoxicity of these quinoxaline N-oxides.