970-15-0Relevant academic research and scientific papers
Activation of the aryl hydrocarbon receptor by methyl yellow and related congeners: structure-activity relationships in halogenated derivatives.
Kato, Taka-aki,Matsuda, Tomonari,Matsui, Saburo,Mizutani, Takaharu,Saeki, Ken-ichi
, p. 466 - 471 (2002)
The aryl hydrocarbon receptor (AhR) is a ligand-activated transcription factor that mediates the biological action of many environmental compounds. Methyl yellow (4-dimethylaminoazobenzene; MY) is a principal azo-dye, and structurally related compounds were subjected to analysis of structure-activity relationships as AhR ligands by using a yeast AhR signaling assay. The effects of halogen-substitution among 23 halogenated MYs on the AhR ligand activity can be summarized as follows: enhancement by halogen-substitution at the ortho-position (2'- and 6'-position), and reduction by substitution at the para-position (4'-position). The greatest enhancement of the ligand activity was observed in 2',6'-dichlorinated MY (13.5-fold of MY), and its AhR ligand activity was very close to that of 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) in the present assay system. In the study of compounds structurally related to MY, benzanilide (BA) showed almost the same AhR ligand activity as azobenzene and trans-stilbene. Furthermore, 4'-chlorobenzanilide, in which the length of the molecule is similar to that of MY, enhanced the AhR ligand activity by ortho(2')-chlorine-substitution, and the AhR ligand activity of 2',4'-dichlorobenzanilide was similar to that of 2'-chloro-MY. These results suggest that the amide bond is equivalent to the -N=N- or -CH=CH- double bond for recognition as the ligand by AhR in 1,2-diphenyl-1,2-ene derivatives.
FLUOROCARBON DERIVATIVES OF NITROGEN. PART 16. SYNTHESIS OF SOME UNSYMMETRICAL AROMATIC AZO-COMPOUNDS via DIAZOTISATION OF FLUORINATED ARYL- AND N-HETEROARYL-AMINES IN HYDROFLUORIC OR SULPHURIC ACID
Alty, Adam C.,Banks, Ronald E.,Thompson, A. Ronald,Vellis, Haralambos S.,Fishwick Brian R.
, p. 147 - 170 (2007/10/02)
Coupling reactions of the type ArFN2+ + ArH -> ArFN=NAr + H+ have been accomplished between fluorinated arenediazonium ions selected from the benzenic, pyridinic and pyrimidinic classes F = C6F5, 4-CF3C6F4, 4-C5F4N, 4-C5F3N.Cl-3, 4-C5F2N.Cl2-3,5, 2-C5F3N.CF(CF3)2-4, 4-C4F3N2> and one or more aromatic compounds activated towards electrophilic attack (ArH = 1,3,5-Me3C6H3, 1,3,5-Et3C6H3, MeOC6H5, Me2NC6H5, and naphth-2-ol).The diazonium ions were generated by addition of solid sodium nitrite to solutions of the amines ArFNH2 in anhydrous hydrogen fluoride, 80percent hydrofluoric acid, or 98 percent sulphuric acid mixed with glacial aceticacid and propionic acid.This work has established that perfluorinated arenediazonium ions rank amongst the most electrophilic species of their general class.
