4-Chlor-3'-methoxy-4'-nitrodiphenylether | 70870-44-9

• 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-Chlor-3'-methoxy-4'-nitrodiphenylether
• 英文别名: 2-Nitro-5-(4-chlorphenoxy)-anisol；2-nitro-5-(4-chlorophenoxy)-anisole；4-(4-chlorophenoxy)-2-methoxy-1-nitrobenzene
• CAS: 70870-44-9
• 化学式: C₁₃H₁₀ClNO₄
• 分子量: 279.68
• InChiKey: MTFWDDPDIRHZGL-UHFFFAOYSA-N

物化性质

• 沸点：
  394.1±27.0 °C(Predicted)
• 密度：
  1.345±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  64.3
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-Chlor-3'-methoxy-4'-nitrodiphenylether 在 亚磷酸三苯酯 、 铁粉 、 氯化铵 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 14.0h， 生成 3,5-dichloro-N-(4-(4-chlorophenoxy)-2-methoxyphenyl)-2-hydroxybenzamide
  参考文献：
  名称：

  Salicylanilide Analog Minimizes Relapse of Clostridioides difficile Infection in Mice

  摘要：

  Clostridioides difficile infection (CDI) causes serious and sometimes fatal symptoms like diarrhea and pseudomem-branous colitis. Although antibiotics for CDI exist, they are either expensive or cause recurrence of the infection due to their altering the colonic microbiota, which is necessary to suppress the infection. Here, we leverage a class of known membrane-targeting compounds that we previously showed to have broad inhibitory activity across multiple Clostridioides difficile strains while preserving the microbiome to develop an efficacious agent. A new series of salicylanilides was synthesized, and the most potent analog was selected through an in vitro inhibitory assay to evaluate its pharmacokinetic parameters and potency in a CDI mouse model. The results revealed reduced recurrence of CDI and diminished disturbance of the microbiota in mice compared to standard-of-care vancomycin, thus paving the way for novel therapy that can potentially target the cell membrane of C. difficile to minimize relapse in the recovering patient.

  DOI：

  10.1021/acs.jmedchem.0c00123
• 作为产物：
  描述：

  5-氟-2-硝基苯甲醚 、 对氯苯酚 在 caesium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 4.0h， 生成 4-Chlor-3'-methoxy-4'-nitrodiphenylether
  参考文献：
  名称：

  Salicylanilide Analog Minimizes Relapse of Clostridioides difficile Infection in Mice

  摘要：

  Clostridioides difficile infection (CDI) causes serious and sometimes fatal symptoms like diarrhea and pseudomem-branous colitis. Although antibiotics for CDI exist, they are either expensive or cause recurrence of the infection due to their altering the colonic microbiota, which is necessary to suppress the infection. Here, we leverage a class of known membrane-targeting compounds that we previously showed to have broad inhibitory activity across multiple Clostridioides difficile strains while preserving the microbiome to develop an efficacious agent. A new series of salicylanilides was synthesized, and the most potent analog was selected through an in vitro inhibitory assay to evaluate its pharmacokinetic parameters and potency in a CDI mouse model. The results revealed reduced recurrence of CDI and diminished disturbance of the microbiota in mice compared to standard-of-care vancomycin, thus paving the way for novel therapy that can potentially target the cell membrane of C. difficile to minimize relapse in the recovering patient.

  DOI：

  10.1021/acs.jmedchem.0c00123

文献信息

• 3-Hydroxydiphenyl ethers
  申请人：Ciba-Geigy Corporation

  公开号：US04268693A1

  公开（公告）日：1981-05-19

  3-Hydroxydiphenyl ethers of the formula ##STR1## wherein R.sub.1 represents hydrogen, fluorine or chlorine, each of R.sub.2 and R.sub.3 independently represents hydrogen or chlorine, and each of R.sub.4, R.sub.5 and R.sub.6 independently represents hydrogen, fluorine, chlorine, bromine or alkyl of 1 to 4 carbon atoms, with the proviso that each phenyl nucleus contains at least one halogen atom, but the total number of halogen atoms in the molecule does not exceed 4, processes for their production and a method of using them for combating micro-organisms.

  公式为##STR1##的3-羟基二苯醚，其中R.sub.1代表氢、氟或氯，R.sub.2和R.sub.3各自独立地代表氢或氯，R.sub.4、R.sub.5和R.sub.6各自独立地代表氢、氟、氯、溴或含有1至4个碳原子的烷基，但苯环中至少含有一个卤原子，分子中的卤原子总数不超过4个，其生产过程以及用于对抗微生物的方法。
• Antimicrobial 3-hydroxydiphenyl ethers
  申请人：Ciba-Geigy Corporation

  公开号：US04339462A1

  公开（公告）日：1982-07-13

  3-Hydroxydiphenyl ethers of the formula ##STR1## wherein R.sub.1 represents hydrogen, fluorine or chlorine, each of R.sub.2 and R.sub.3 independently represents hydrogen or chlorine, and each of R.sub.4, R.sub.5 and R.sub.6 independently represents hydrogen, fluorine, chlorine, bromine or alkyl of 1 to 4 carbon atoms, with the proviso that each phenyl nucleus contains at least one halogen atom, but the total number of halogen atoms in the molecule does not exceed 4, processes for their production and a method of using them for combating micro-organisms.

  公式为##STR1##的3-羟基二苯醚，其中R.sub.1代表氢、氟或氯，每个R.sub.2和R.sub.3独立地代表氢或氯，每个R.sub.4、R.sub.5和R.sub.6独立地代表氢、氟、氯、溴或1至4个碳原子的烷基，但苯环中至少含有一个卤素原子，但分子中卤素原子的总数不超过4，其制备方法以及用于抗击微生物的方法。
• US4268693A
  申请人：——

  公开号：US4268693A

  公开（公告）日：1981-05-19
• US4339462A
  申请人：——

  公开号：US4339462A

  公开（公告）日：1982-07-13
• US6316386B1
  申请人：——

  公开号：US6316386B1

  公开（公告）日：2001-11-13