2-ethyl-N-(2-hydroxy-5-nitrophenyl)butanamide | 1011574-38-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-ethyl-N-(2-hydroxy-5-nitrophenyl)butanamide
• CAS: 1011574-38-1
• 化学式: C₁₂H₁₆N₂O₄
• 分子量: 252.27
• InChiKey: UUPJTXNHOAPLAK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-ethyl-N-(2-hydroxy-5-nitrophenyl)butanamide 在 硫酸 、 palladium 10% on activated carbon 、 palladium on activated charcoal 、 氢气 、 硝酸 、 碳酸氢钠 、 potassium carbonate 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醇 、 水 、 丙酮 为溶剂， 反应 12.17h， 生成
  参考文献：
  名称：

  Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors

  摘要：

  Eight series of compounds, each series containing two to five compounds were prepared by structural modifications of a lead, which was previously discovered as a mild influenza neuraminidase (NA) inhibitor. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. Several caffeic acid derivatives that acted as non-competitive inhibitors were close or superior to the lead and also presented good antiviral activities in cells. Besides, it was interesting to find that modifications of the lead with different strategies could result in selective inhibition against N1 or N2. The preliminary docking analysis indicated that the 150-cavity of the enzymes played an important role in the selective inhibition. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.020
• 作为产物：
  描述：

  2-乙基丁酰氯 、 2-氨基-4-硝基苯酚 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 2-ethyl-N-(2-hydroxy-5-nitrophenyl)butanamide
  参考文献：
  名称：

  Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors

  摘要：

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.033

文献信息

• Caffeic acid derivatives: A new type of influenza neuraminidase inhibitors
  作者：Yuanchao Xie、Bing Huang、Kexiang Yu、Fangyuan Shi、Tianqi Liu、Wenfang Xu

  DOI：10.1016/j.bmcl.2013.04.033

  日期：2013.6

  Recently, many natural products, especially some plant-derived polyphenols have been found to exert antiviral effects against influenza virus and show inhibitory activities on neuraminidases (NAs). In our research, we took caffeic acid which contained two phenolic hydroxyl groups as the basic fragment to build a small compound library with various structures. The enzyme inhibition result indicated that some compounds exhibited moderate activities against NA and compound 15d was the best with IC50 = 7.2 mu M and 8.5 mu M against N2 and N1 NAs, respectively. The 3,4-dihydroxyphenyl group from caffeic acid was important for the activity according to the docking analysis. Besides, compound 15d was found to be a non-competitive inhibitor with K-i = 11.5 +/- 0.25 mu M by the kinetic study and also presented anti-influenza virus activity in chicken embryo fibroblast cells. It seemed promising to discover more potent NA inhibitors from caffeic acid derivatives to cope with influenza virus. (C) 2013 Elsevier Ltd. All rights reserved.
• Further discovery of caffeic acid derivatives as novel influenza neuraminidase inhibitors
  作者：Yuanchao Xie、Bing Huang、Kexiang Yu、Wenfang Xu

  DOI：10.1016/j.bmc.2013.10.020

  日期：2013.12

  Eight series of compounds, each series containing two to five compounds were prepared by structural modifications of a lead, which was previously discovered as a mild influenza neuraminidase (NA) inhibitor. On the basis of the biological result, a detailed structure-activity relationship (SAR) was derived and discussed. Several caffeic acid derivatives that acted as non-competitive inhibitors were close or superior to the lead and also presented good antiviral activities in cells. Besides, it was interesting to find that modifications of the lead with different strategies could result in selective inhibition against N1 or N2. The preliminary docking analysis indicated that the 150-cavity of the enzymes played an important role in the selective inhibition. (C) 2013 Elsevier Ltd. All rights reserved.