4-amino-2'-nitrodiphenyl sulfide | 93352-49-9

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-amino-2'-nitrodiphenyl sulfide
• 英文别名: 3-(2-Nitrophenyl)sulfanylaniline
• CAS: 93352-49-9
• 化学式: C₁₂H₁₀N₂O₂S
• 分子量: 246.29
• InChiKey: DUQFOADXVQZWNL-UHFFFAOYSA-N

物化性质

• 沸点：
  420.4±30.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  17
• 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：

  4-amino-2'-nitrodiphenyl sulfide 在 镍 吡啶 、 氢气 作用下， 以 乙醇 为溶剂， 80.0 ℃ 、10.0 MPa 条件下， 反应 13.0h， 生成 N,N'-bis[3-(2-aminophenyl)sulfanylphenyl]heptanediamide
  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 、 硝基氯苯 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以70%的产率得到4-amino-2'-nitrodiphenyl sulfide
  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

文献信息

• Structure-activity relationships in 2-aminodiphenylsulfides against trypanothione reductase from Trypanosoma cruzi
  作者：Sophie Girault、Elisabeth Davioud-Charvet、Laurence Salmon、Amaya Berecibar、Marie-Ange Debreu、Christian Sergheraert

  DOI：10.1016/s0960-894x(98)00180-2

  日期：1998.5

  In order to establish structural elements responsible for inhibition of trypanothione reductase (TR) from Trypanosoma cruzi by 2-aminodiphenylsulfides, a series of dissymmetrical derivatives, corresponding to the replacement of one aromatic moiety by different amines, was synthesized. TR inhibition studies revealed the importance of the aromatic rings and of the amino groups in the side chains for potent inhibition. Quinonic moities were also introduced with the aim of acting as TR redox-cycling substrates. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Pilyugin; Kiseleva; Chikisheva, Russian Journal of General Chemistry, 2000, vol. 70, # 4, p. 568 - 569
  作者：Pilyugin、Kiseleva、Chikisheva、Klimakova、Vorob'eva、Kuznetsova、Valitov

  DOI：——

  日期：——