2-Acetyl-3-trifluormethylchinoxalin-di-N-oxid | 33578-42-6

• 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: 2-Acetyl-3-trifluormethylchinoxalin-di-N-oxid
• 英文别名: 1,4-di-N-oxide-2-acethyl-3-trifluoromethylquinoxaline；1-[4-oxido-1-oxo-3-(trifluoromethyl)quinoxalin-1-ium-2-yl]ethanone
• CAS: 33578-42-6
• 化学式: C₁₁H₇F₃N₂O₃
• 分子量: 272.183
• InChiKey: OLTLCPGFNFJXOB-UHFFFAOYSA-N

物化性质

• 熔点：
  175-176 °C
• 沸点：
  451.5±55.0 °C(Predicted)
• 密度：
  1.51±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  63.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  苯并呋咱 、 三氟乙酰丙酮 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 2-Acetyl-3-trifluormethylchinoxalin-di-N-oxid
  参考文献：
  名称：

  Synthesis and anticancer activity evaluation of new 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethyl-quinoxaline 1,4-di-N-oxide derivatives

  摘要：

  As a continuation of our research in quinoxaline 1,4-di-N-oxide and with the aim of obtaining new anticancer agents, which can improve the current chemotherapeutic treatments, new series of 2-alkylcarbonyl and 2-benzoyl-3-trifluoromethylquinoxaline 1,4-di-N-oxide derivatives have been synthesized and evaluated for in vitro antitumor activity against a 3-cell line panel, consisting of MCF7 (breast), NCI-H460 (lung), and SF-268 (CNS). These active compounds were then evaluated in the full panel of 60 human tumor cell lines derived from nine cancer cell types. The results have shown that, in general, anticancer activity depends on the substituents in the carbonyl group, improving in the order: ethyl < isopropyl < tert-butyl < phenyl-ones. Among these, the compounds 4c, 6e, their difluorinated analogs (4g and 6g), and 5c were the most active, with mean GI(50) values of 1.02, 0.42, 0.52, 0.15, and 0.49 muM, respectively. All of them were also found to inhibit the growth of the all of the Leukemia cell lines studied (with 75% of the GI(50) values less than 0.15 muM) and therefore, were selected for further evaluation for the in vivo hollow fiber assays. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.04.013