3-(4-chloro-2-nitrophenylthio)aniline | 188058-97-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3-(4-chloro-2-nitrophenylthio)aniline
• 英文别名: 3-(4-Chloro-2-nitrophenyl)sulfanylaniline
• CAS: 188058-97-1
• 化学式: C₁₂H₉ClN₂O₂S
• 分子量: 280.735
• InChiKey: WTOKGNGZVMEDKF-UHFFFAOYSA-N

物化性质

• 沸点：
  447.8±45.0 °C(Predicted)
• 密度：
  1.47±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 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：
  97.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-chloro-2-nitrophenylthio)aniline 在 N-乙基哌啶 、 吡啶 、 盐酸 、 铁粉 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 14.5h， 生成 N,N'-bis[3-[4-chloro-2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylphenyl]pentanediamide
  参考文献：
  名称：

  New potent inhibitors of trypanothione reductase from Trypanosoma cruzi in the 2-aminodiphenylsulfide series

  摘要：

  From a screening assay, 2-aminodiphenylsulfides were selected as leads for trypanothione reductase (TR) inhibition and studied by molecular modelling in the catalytic site of the enzyme. A series of analogues, monomers or bis-derivatives, were synthesized to improve binding energy and therefore inhibiting potency. These compounds appeared to be mixed competitive TR inhibitors and their inhibition profile could be explained when their aggregation in solution was taken into consideration. A bis-amino-diphenylsulfide with an IC50 of 0.55 mu M was revealed to be the best TR inhibitor described so far.

  DOI：

  10.1016/s0223-5234(97)84360-7
• 作为产物：
  描述：

  3-氨基苯硫酚 、 2,5-二氯硝基苯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以32%的产率得到3-(4-chloro-2-nitrophenylthio)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

• New potent inhibitors of trypanothione reductase from Trypanosoma cruzi in the 2-aminodiphenylsulfide series
  作者：S Girault、S Baillet、D Horvath、V Lucas、E Davioud-Charvet、A Tartar、C Sergheraert

  DOI：10.1016/s0223-5234(97)84360-7

  日期：1997.1

  From a screening assay, 2-aminodiphenylsulfides were selected as leads for trypanothione reductase (TR) inhibition and studied by molecular modelling in the catalytic site of the enzyme. A series of analogues, monomers or bis-derivatives, were synthesized to improve binding energy and therefore inhibiting potency. These compounds appeared to be mixed competitive TR inhibitors and their inhibition profile could be explained when their aggregation in solution was taken into consideration. A bis-amino-diphenylsulfide with an IC50 of 0.55 mu M was revealed to be the best TR inhibitor described so far.
• 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.