4-(2-chloro-4-nitrophenoxy)aniline | 26076-39-1

• 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-(2-chloro-4-nitrophenoxy)aniline
• 英文别名: 4-Amino-2'-chlor-4'-nitro-diphenylether
• CAS: 26076-39-1
• 化学式: C₁₂H₉ClN₂O₃
• 分子量: 264.668
• InChiKey: PCYUQEVKVCLHDL-UHFFFAOYSA-N

物化性质

• 沸点：
  385.7±37.0 °C(Predicted)
• 密度：
  1.422±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 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：

  4-(2-chloro-4-nitrophenoxy)aniline 、 5-硝基水杨酸 在 N,N-二甲基甲酰胺 、 三氯化磷 作用下， 以 氯苯 为溶剂， 反应 2.0h， 以22%的产率得到N-[4-(2-chloro-4-nitrophenoxy)phenyl]-2-hydroxy-5-nitrobenzamide
  参考文献：
  名称：

  Structure-activity relationships of antifilarial antimycin analogs: a multivariate pattern recognition study

  摘要：

  The structure-activity relationships of a series of novel antifilarial antimycin A1 analogues have been investigated by using computational chemistry and multivariate statistical techniques. The physiochemical descriptors calculated in this way contained information which was useful in the classification of compounds according to their in vitro antifilarial activity. This approach generated a 53 parameter descriptor set, which was reduced with a multivariate pattern recognition package, ARTHUR. Regression analysis of the reduced set yielded several statistically significant regression equations; e.g.-log in vitro activity = 0.017 mp + 0.65 log P - 0.81ESDL10-7.33 (R = 0.9). With use of this equation, it was possible to make predictions for further untested analogues. The analysis indicated that membrane or lipid solubility is an important determinant in biological activity agreeing with the proposed primary mode of action of the compounds as disrupters of cuticular glucose uptake.

  DOI：

  10.1021/jm00163a023
• 作为产物：
  描述：

  3-氯-4-氟硝基苯 、 对氨基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以54%的产率得到4-(2-chloro-4-nitrophenoxy)aniline
  参考文献：
  名称：

  Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors

  摘要：

  A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.

  DOI：

  10.1021/jm501090m

文献信息

• US4005223A
  申请人：——

  公开号：US4005223A

  公开（公告）日：1977-01-25
• Structure-activity relationships of antifilarial antimycin analogs: a multivariate pattern recognition study
  作者：David L. Selwood、David J. Livingstone、John C. W. Comley、Alan B. O'Dowd、Alan T. Hudson、Peter Jackson、Karamjit S. Jandu、Valerie S. Rose、Jeremy N. Stables

  DOI：10.1021/jm00163a023

  日期：1990.1

  The structure-activity relationships of a series of novel antifilarial antimycin A1 analogues have been investigated by using computational chemistry and multivariate statistical techniques. The physiochemical descriptors calculated in this way contained information which was useful in the classification of compounds according to their in vitro antifilarial activity. This approach generated a 53 parameter descriptor set, which was reduced with a multivariate pattern recognition package, ARTHUR. Regression analysis of the reduced set yielded several statistically significant regression equations; e.g.-log in vitro activity = 0.017 mp + 0.65 log P - 0.81ESDL10-7.33 (R = 0.9). With use of this equation, it was possible to make predictions for further untested analogues. The analysis indicated that membrane or lipid solubility is an important determinant in biological activity agreeing with the proposed primary mode of action of the compounds as disrupters of cuticular glucose uptake.
• Modulation of cAMP-Specific PDE without Emetogenic Activity: New Sulfide-Like PDE7 Inhibitors
  作者：Ana M. García、José Brea、Jose A. Morales-García、Daniel I. Perez、Alejandro González、Sandra Alonso-Gil、Irene Gracia-Rubio、Clara Ros-Simó、Santiago Conde、María Isabel Cadavid、María Isabel Loza、Ana Perez-Castillo、Olga Valverde、Ana Martinez、Carmen Gil

  DOI：10.1021/jm501090m

  日期：2014.10.23

  A forward chemical genetic approach was followed to discover new targets and lead compounds for Parkinson's disease (PD) treatment. By analysis of the cell protection produced by some small molecules, a diphenyl sulfide compound was revealed to be a new phosphodiesterase 7 (PDE7) inhibitor and identified as a new hit. This result allows us to confirm the utility of PDE7 inhibitors as a potential pharmacological treatment of PD. On the basis of these data, a diverse family of diphenyl sulfides has been developed and pharmacologically evaluated in the present work. Moreover, to gain insight into the safety of PDE7 inhibitors for human chronic treatment, we evaluated the new compounds in a surrogate emesis model, showing nonemetic effects.