The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: 3-Bromo-4-chloronitrobenzene( cas:16588-26-4 ) is researched.Product Details of 16588-26-4.van der Aar, Ellen M.; de Groot, Marcel J.; Bijloo, Greetje J.; van der Goot, Henk; Vermeulen, Nico P. E. published the article 《Structure-Activity Relationships for the Glutathione Conjugation of 2-Substituted 1-Chloro-4-nitrobenzenes by Rat Glutathione S-Transferase 4-4》 about this compound( cas:16588-26-4 ) in Chemical Research in Toxicology. Keywords: glutathione conjugation chloronitrobenzene transferase. Let’s learn more about this compound (cas:16588-26-4).
In the present study structure-activity relationships (SAR’s) are described for the exptl. determined kinetic parameters (Km, kcat, and kcat/Km) of the GST 4-4-catalyzed reaction between GSH and 10 2-substituted 1-chloro-4-nitrobenzenes. Steric, lipophilic, and electronic parameters were correlated with the kinetic parameters. Moreover, charge distributions and several energy values were calculated for the substrates and the corresponding Meisenheimer intermediates with MeS- as a model nucleophile for the thiolate anion of GSH and used in the regression analyses. The correlations obtained were compared with the corresponding SAR’s for the base-catalyzed GSH conjugation reaction at pH 9.2. A high correlation coefficient was found between the kinetic parameter ks for the base-catalyzed reaction and the Hammett substituent constant (σp). Much lower correlation coefficients were obtained with kcat and σp and with kcat/Km and σp. Moreover, the reaction constant ρ was significantly higher for the base-catalyzed than for the enzyme-catalyzed reaction. Also, high correlations were found between the kinetic parameters and the charges on the p-nitro substituent in the substrates. When ks was plotted against these charges, a linear relation was found in which the slope was larger than the slope of a corresponding plot with kcat/Km. The Hammett σp can be divided into an inductive (F) and a resonance (R) component. With multiple regression between the kinetic parameters and F and R, higher correlation coefficients were obtained than with σp alone. The observations suggest that the transition states for the base-catalyzed and the GST 4-4-catalyzed GSH conjugation reaction are different. Moreover, single classical physicochem. and computer-calculated mol. parameters and combinations of them can be an alternative approach for examining SAR’s for spontaneous and GST-catalyzed GSH conjugation reactions.
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