So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.van der Aar, Ellen M.; de Groot, Marcel J.; Bouwman, Tialda; Bijloo, Greetje J.; Commandeur, Jan N. M.; Vermeulen, Nico P. E. researched the compound: 3-Bromo-4-chloronitrobenzene( cas:16588-26-4 ).Electric Literature of C6H3BrClNO2.They published the article 《4-Substituted 1-Chloro-2-nitrobenzenes: Structure-Activity Relationships and Extension of the Substrate Model of Rat Glutathione S-Transferase 4-4》 about this compound( cas:16588-26-4 ) in Chemical Research in Toxicology. Keywords: chloronitrobenzene glutathione transferase kinetics structure. We’ll tell you more about this compound (cas:16588-26-4).
In the present study, eleven 4-substituted 1-chloro-2-nitrobenzenes were tested for their GSH conjugation capacity when catalyzed by base or rat glutathione S-transferase (GST) 4-4. Kinetic parameters (ks and Km, kcat, and kcat/Km) were determined and subsequently used for the description of structure-activity relationships (SAR’s). For this purpose, eight physicochem. parameters (electronic, steric, and lipophilic) of the substituents and five computer-calculated parameters of the substrates (charge distributions and several energy values) were used in regression analyses with the kinetic parameters. The obtained SAR’s are compared with corresponding SAR’s for the GSH conjugation of 2-substituted 1-chloro-4-nitrobenzenes, previously determined [van der Aar et al. (1996) Chem. Res. Toxicol. 9, 527-534]. The kinetic parameters of the 4-substituted 1-chloro-2-nitrobenzenes correlated well with the Hammett σp- constant: the Hammett σp constant corrected for “”through resonance”” while the corresponding kinetic parameters of the 2-substituted 1-chloro-4-nitrobenzenes did not. The base- and GST 4-4-catalyzed GSH conjugation reactions of 2-substituted 1-chloro-4-nitrobenzenes depend to a different extent on the electronic properties of the ortho substituents, suggesting the involvement of different rate-limiting transition states. The base- and GST 4-4-catalyzed conjugation of 4-substituted 1-chloro-2-nitrobenzenes, however, showed a similar dependence on the electronic properties of the para substituents, indicating that these substrates are conjugated to GSH via a similar transition state. Multiple regression analyses revealed that, besides electronic interactions, also steric and lipophilic restrictions appeared to play an important role in the GST 4-4-catalyzed GSH conjugation of 4-substituted 1-chloro-2-nitrobenzenes. Finally, the 4-substituted 1-chloro-2-nitrobenzenes were also used to extend the previously described substrate model for GST 4-4 [De Groot et al. (1995) Chem. Res. Toxicol. 8, 649-658], by which a specific steric restriction of substrates for GST 4-4 became clear.
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