3-(2-amino)phenylthiophenylamine | 27332-24-7

• 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-(2-amino)phenylthiophenylamine
• 英文别名: 2-(3-Aminophenyl)sulfanylaniline；2-(3-aminophenyl)sulfanylaniline
• CAS: 27332-24-7
• 化学式: C₁₂H₁₂N₂S
• 分子量: 216.307
• InChiKey: PCDFPAKSBQNCNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  15
• 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：
  77.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(2-amino)phenylthiophenylamine 在 N-乙基哌啶 作用下， 以 四氢呋喃 为溶剂， 反应 5.5h， 生成 3-(4-methylpiperazin-1-yl)-N-[3-[2-[3-(4-methylpiperazin-1-yl)propanoylamino]phenyl]sulfanylphenyl]propanamide
  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：

  3,3'-二硝基二苯二硫醚 在 palladium on activated charcoal 氢气 作用下， 生成 3-(2-amino)phenylthiophenylamine
  参考文献：
  名称：

  Chemistry of the sulfur--nitrogen bond. I. Thermal reactions of nitrobenzenesulfenanilides

  摘要：

  DOI：

  10.1021/jo00805a014

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.
• 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.
• Chemistry of the sulfur--nitrogen bond. I. Thermal reactions of nitrobenzenesulfenanilides
  作者：Franklin Arnold Davis、Ronald B. Wetzel、Thomas J. Devon、Joseph F. Stackhouse

  DOI：10.1021/jo00805a014

  日期：1971.3