[3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine | 188059-02-1

• 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-bromo-2-nitro)phenylsulfanyl]phenylamine
• 英文别名: 3-(4-Bromo-2-nitrophenyl)sulfanylaniline
• CAS: 188059-02-1
• 化学式: C₁₂H₉BrN₂O₂S
• 分子量: 325.186
• InChiKey: DOIKJQKEBLFCON-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 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-bromo-2-nitro)phenylsulfanyl]phenylamine 在 吡啶 、 盐酸 作用下， 反应 4.0h， 生成 4-[3-(4-Bromo-2-nitro-phenylsulfanyl)-phenylcarbamoyl]-butyric acid methyl ester
  参考文献：
  名称：

  Structure-activity relationships in 2-aminodiphenylsulfides against trypanothione reductase from Trypanosoma cruzi

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(98)00180-2
• 作为产物：
  描述：

  2,5-二溴硝基苯 、 3-氨基苯硫酚 在 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 36.0h， 以84%的产率得到[3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine
  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

• 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.
• Potent and specific inhibitors of trypanothione reductase from Trypanosoma cruzi
  作者：Sophie Girault、Elisabeth Davioud-Charvet、Louis Maes、Jean-François Dubremetz、Marie-Ange Debreu、Valérie Landry、Christian Sergheraert

  DOI：10.1016/s0968-0896(00)00312-6

  日期：2001.4

  In order to optimise the activity of bis(2-aminodiphenylsulfides) upon trypanothione reductase (TR) from Trypanosoma cruzi, a new series of bis(2-aminodiphenylsulfides) possessing three side chains was synthesized. Various moieties were introduced at the end of the third side chain. including acridinyl or biotinyl moieties for fluorescent labeling studies. TR inhibition was improved: the most potent inhibitor (IC50 = 200 nM) was selective towards TR versus human glutathione reductase and corresponded to a single myristyl group. Compounds were also tested in vitro upon Trypanosoma cruzi and Leishmania infantum amastigotes, upon Trypanosoma brucei trypomastigotes, and for their cytotoxicity upon human MRC-5 cells. In the presence of serum, acridine derivative was no longer detectable in mass spectrometry and its antitrypanosomal activity no longer observed. This transformation might explain the absence of correlation between the potent TR inhibition and the in vitro and in vivo antiparasitic activity with both of the first generation of 2-aminodiphenylsulfides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.