0000000000410066
AUTHOR
M. C. Sarva
Substituent effect on the redox potential of substituted (aryl)(2-nitrobenzo[ b ]thiophen-3-yl)amines
Abstract The electronic effect of some meta- or para-substituents on the reduction of the title compounds has been investigated. The reversible reduction potential values of these compounds have been evaluated by cyclic voltammetry at a mercury electrode in 0.1 M tetraethylammoniumtetrafluoroborate, dimethylsulfoxide solutions. The substituent effect depends on both its nature and its position. The reduction potential values of the derivatives studied have been correlated with the Hammett substituent constants.
Influence of nitroreductase and O-acetyltransferase on the mutagenicity of substituted nitrobenzothiophenamines in Salmonella typhimurium.
The mutagenic activity of 17 substituted (aryl)(2-nitrobenzo[b]thiophen-3yl)amines has been evaluated in the Ames test with different isogenic strains of Salmonella typhimurium, that varied in their expression of nitroreductase and O-acetyltransferase. Active derivatives induced frameshift mutations in TA98 strain, and differences in the chemical structure resulted in up to 15-fold changes in mutagenic activity. The non-mutagenic compounds are the unsubstituted parent compound and derivatives with para-chloro, para-fluoro, para-diethylamino, meta-bromo and para-dimethylamino groups. They do not show any activity even in strains with higher level of nitroreductase or O-acetyltransferase. The…
Analysis of13C NMR substituent chemical shifts in some (aryl)(2-nitrobenzo [b]thiophen-3-yl)amines: A new class of compounds with analgesic, anti-exudative and anti-inflammatory activities showing low mutagenicity
The 13C NMR chemical shift values of (aryl)(2-nitrobenzo[b]thiophen-3-yl)amines were measured in DMSO-d6 solutions, suggesting the occurrence of an alternate charge polarization at C-3, C-2, C-3a, C-7a, C-4 and C-5. A dual substituent parameter analysis of the experimental data indicates a large or a low resonance contribution for aryl para or meta substituents, respectively, while the inductive component remains constant throughout.