2,3-bis(3-methoxyphenyl)-6-nitroquinoxaline | 858364-16-6

• 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: 2,3-bis(3-methoxyphenyl)-6-nitroquinoxaline
• CAS: 858364-16-6
• 化学式: C₂₂H₁₇N₃O₄
• 分子量: 387.395
• InChiKey: LWBFXTOCHYGBNB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3-bis(3-methoxyphenyl)-6-nitroquinoxaline 在 乙硫醇钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以71%的产率得到3-[3-(3-Hydroxyphenyl)-6-nitroquinoxalin-2-yl]phenol
  参考文献：
  名称：

  Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors

  摘要：

  A library of quinoxaline derivatives were prepared to target non-structural protein 1 of influenza A (NS1A) as a means to develop anti-influenza drug leads. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsRNA-NS1A interaction to varying extents. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to variance in responses. The most active compounds (35 and 44) had IC50 values in the range of low micromolar concentration without exhibiting significant dsRNA intercalation. Compound 44 was able to inhibit influenza A/Udorn/72 virus growth. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.042
• 作为产物：
  描述：

  3,3'-二甲氧基苯偶酰 、 4-硝基邻苯二胺 在 Graphite 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以81%的产率得到2,3-bis(3-methoxyphenyl)-6-nitroquinoxaline
  参考文献：
  名称：

  石墨催化喹喔啉的绿色合成

  摘要：

  描述了一种使用环境友好，廉价且易于回收的石墨作为多相催化剂合成喹喔啉的简单方法。通过在室温下在乙醇中以71-93％的收率将取代的苯，菲-9,10-二酮和安息香与芳香族二胺进行双缩合，制得一个具有药理学意义的二苯基喹喔啉文库。脂肪族二胺以72-92％的产率从取代的苯甲醚中生成相应的二氢吡嗪。

  DOI：

  10.1016/j.tetlet.2012.12.041

文献信息

• Graphite catalyzed green synthesis of quinoxalines
  作者：Hari K. Kadam、Salman Khan、Rupesh A. Kunkalkar、Santosh G. Tilve

  DOI：10.1016/j.tetlet.2012.12.041

  日期：2013.2

  A new simple approach using environmentally benign, cheap, and easily recyclable graphite as a heterogeneous catalyst for the synthesis of quinoxalines is described. A library of pharmacologically interesting diphenylquinoxalines is prepared by the double condensation of substituted benzils, phenanthrene-9,10-dione, and benzoin with aromatic diamines in 71–93% yields at room temperature in ethanol

  描述了一种使用环境友好，廉价且易于回收的石墨作为多相催化剂合成喹喔啉的简单方法。通过在室温下在乙醇中以71-93％的收率将取代的苯，菲-9,10-二酮和安息香与芳香族二胺进行双缩合，制得一个具有药理学意义的二苯基喹喔啉文库。脂肪族二胺以72-92％的产率从取代的苯甲醚中生成相应的二氢吡嗪。
• Synthesis and evaluation of quinoxaline derivatives as potential influenza NS1A protein inhibitors
  作者：Lei You、Eun Jeong Cho、John Leavitt、Li-Chung Ma、Gaetano T. Montelione、Eric V. Anslyn、Robert M. Krug、Andrew Ellington、Jon D. Robertus

  DOI：10.1016/j.bmcl.2011.03.042

  日期：2011.5

  A library of quinoxaline derivatives were prepared to target non-structural protein 1 of influenza A (NS1A) as a means to develop anti-influenza drug leads. An in vitro fluorescence polarization assay demonstrated that these compounds disrupted the dsRNA-NS1A interaction to varying extents. Changes of substituent at positions 2, 3 and 6 on the quinoxaline ring led to variance in responses. The most active compounds (35 and 44) had IC50 values in the range of low micromolar concentration without exhibiting significant dsRNA intercalation. Compound 44 was able to inhibit influenza A/Udorn/72 virus growth. (C) 2011 Elsevier Ltd. All rights reserved.