188059-02-1

Basic information

• Product Name: [3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine
• Synonyms: [3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine
• CAS NO: 188059-02-1
• Molecular Weight: 325.186
• Mol File: 188059-02-1.mol

Chemical Properties

• CAS DataBase Reference: [3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine(CAS DataBase Reference)
• NIST Chemistry Reference: [3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine(188059-02-1)
• EPA Substance Registry System: [3-(4-bromo-2-nitro)phenylsulfanyl]phenylamine(188059-02-1)

Safety Data

• Hazardous Substances Data: 188059-02-1(Hazardous Substances Data)

Upstream product

• 3460-18-2 1,4-dibromo-2-nitrobenzene 
• 22948-02-3 3-aminothiophenol 

Downstream Products

• 209608-37-7 4-[3-(4-Bromo-2-nitro-phenylsulfanyl)-phenylcarbamoyl]-butyric acid 
• 188059-05-4 Pentanedioic acid bis-[(3-{4-bromo-2-[3-(4-methyl-piperazin-1-yl)-propionylamino]-phenylsulfanyl}-phenyl)-amide] 
• 188059-04-3 Pentanedioic acid bis-{[3-(2-amino-4-bromo-phenylsulfanyl)-phenyl]-amide} 

Relevant articles and documents

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

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.

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

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-aminodiphenylsulfide with an IC50 of 0.55 μM was revealed to be the best TR inhibitor described so far.