4-nitro-3-(trifluoromethyl)benzhydrazide | 1333392-75-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-nitro-3-(trifluoromethyl)benzhydrazide
• 英文别名: 4-Nitro-3-(trifluoromethyl)benzhydrazide；4-nitro-3-(trifluoromethyl)benzohydrazide
• CAS: 1333392-75-8
• 化学式: C₈H₆F₃N₃O₃
• 分子量: 249.149
• InChiKey: JBCIFTGKBUJKQV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-nitro-3-(trifluoromethyl)benzhydrazide 、 2,1,3-苯噁二唑-5-甲醛 1-氧化物 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以73%的产率得到4-nitro-3-(trifluoromethyl)-[N'-(benzofuroxan-5-yl)methylene]benzhydrazide
  参考文献：
  名称：

  Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss’ decision tree, synthesis and biological assay

  摘要：

  The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N'-(benzofuroxan-5-yl) methylene] benzhydrazide (MIC range 12.7-11.4 mu g/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.034
• 作为产物：
  描述：

  4-nitro-3-(trifluoromethyl)benzoic acid methyl ester 在 一水合肼 作用下， 以 水 为溶剂， 反应 1.0h， 以66%的产率得到4-nitro-3-(trifluoromethyl)benzhydrazide
  参考文献：
  名称：

  Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss’ decision tree, synthesis and biological assay

  摘要：

  The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N'-(benzofuroxan-5-yl) methylene] benzhydrazide (MIC range 12.7-11.4 mu g/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.034

文献信息

• Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss’ decision tree, synthesis and biological assay
  作者：Salomão Dória Jorge、Fanny Palace-Berl、Andrea Masunari、Cléber André Cechinel、Marina Ishii、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2011.06.034

  日期：2011.8

  The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N'-(benzofuroxan-5-yl) methylene] benzhydrazide (MIC range 12.7-11.4 mu g/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively. (C) 2011 Elsevier Ltd. All rights reserved.