3-(3,4-dichlorophenoxy)-2-nitroaniline

• 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: 3-(3,4-dichlorophenoxy)-2-nitroaniline
• 英文别名: 3-(3,4-Dichlorophenoxy)-2-nitroaniline
• 化学式: C₁₂H₈Cl₂N₂O₃
• 分子量: 299.113
• InChiKey: LLYPMNQNZVMMEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(3,4-dichlorophenoxy)-2-nitroaniline 在 tin(II) chloride dihdyrate 作用下， 以 甲醇 为溶剂， 以60%的产率得到3-(3,4-dichlorophenoxy)benzene-1,2-diamine
  参考文献：
  名称：

  Cinnamonitrile Adjuvants Restore Susceptibility to β-Lactams against Methicillin-Resistant Staphylococcus aureus

  摘要：

  beta-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the beta-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 mu M (E)-3-(5-(3,4-dichlorobenzy1)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg.L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.

  DOI：

  10.1021/acsmedchemlett.9b00169
• 作为产物：
  描述：

  2,6-二氟硝基苯 在 ammonium hydroxide 、 potassium tert-butylate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 3-(3,4-dichlorophenoxy)-2-nitroaniline
  参考文献：
  名称：

  Cinnamonitrile Adjuvants Restore Susceptibility to β-Lactams against Methicillin-Resistant Staphylococcus aureus

  摘要：

  beta-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the beta-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 mu M (E)-3-(5-(3,4-dichlorobenzy1)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg.L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.

  DOI：

  10.1021/acsmedchemlett.9b00169

文献信息

• Cinnamonitrile Adjuvants Restore Susceptibility to β-Lactams against Methicillin-Resistant <i>Staphylococcus aureus</i>
  作者：Enrico Speri、Choon Kim、Stefania De Benedetti、Yuanyuan Qian、Elena Lastochkin、Jennifer Fishovitz、Jed F. Fisher、Shahriar Mobashery

  DOI：10.1021/acsmedchemlett.9b00169

  日期：2019.8.8

  beta-Lactams are used routinely to treat Staphylococcus aureus infections. However, the emergence of methicillin-resistant S. aureus (MRSA) renders them clinically precarious. We describe a class of cinnamonitrile adjuvants that restore the activity of oxacillin (a penicillin member of the beta-lactams) against MRSA. The lead adjuvants were tested against six important strains of MRSA, one vancomycin-intermediate S. aureus (VISA) strain, and one linezolid-resistant S. aureus strain. Five compounds out of 84 total compounds showed broad potentiation. At 8 mu M (E)-3-(5-(3,4-dichlorobenzy1)-2-(trifluoromethoxy)phenyl)-2-(methylsulfonyl)acrylonitrile (26) potentiated oxacillin with a >4000-fold reduction of its MIC (from 256 to 0.06 mg.L-1). This class of adjuvants holds promise for reversal of the resistance phenotype of MRSA.