126875-80-7Relevant academic research and scientific papers
Synthesis and characterization of model ultimate carcinogens/metabolites derived from lead tetraacetate oxidation of arylnitrones: 2′-Deoxyguanosine adducts
Mallesha,Kumar,Mantelingu,Rangappa
, p. 1459 - 1461 (2007/10/03)
The synthesis of model reactive metabolites 4a-c by lead tetraacetate (LTA) oxidation of arylnitrones 3a-c is described. Compounds 4a-c react with deoxyguanosine (dG) to give N-benzoylated C8-adducts 5a-c. Following debenzoylation with the heterogeneous system (sodium carbonate/methanol) leads to the corresponding C8-adducts 6a-c.
N-Aryl-O-(α-aminoacyl)hydroxylamines: Model Reactions with Deoxyguanosine, Guanosine and 5'-Guanosinemonophosphate for the Activation of Monocyclic Aromatic Amines (e.g. Phenacetin) into Ultimate Carcinogens
Meier, Chris,Boche, Gernot
, p. 1699 - 1705 (2007/10/02)
In in vitro model reactions of the activation of monocyclic aromatic amines by α-amino acids it is shown that α-aminohydroxamic acids 8 and 9 rearrange base-catalyzed to N-(α-aminoacyloxy)arylamines 10 and 11 which react with bionucleophiles such as deoxyguanosine (dG) (12), guanosine (G) (13) and 5'-guanosinemonophosphate (5'-GMP) (14) to form adducts.We describe the regioselective formation of the C-8 adducts of 4-chloroaniline (15), aniline (16), 4-methylaniline (17), and 4-methoxyaniline (18), respectively, , and also of N-(guanosine-8-yl)-4-methylaniline (21) and 8-(4-methylanilino)-5'-guanosinemonophosphate (22).Similar reactions of the N-(acetoxy)arylamines 20, which are very likely to be "ultimate" carcinogens of aromatic amines, lead to the same C-8 adducts 15-18, 21, and 22 in comparable yields.These in vitro reactions thus show that the N-(α-aminoacyloxy)arylamines 10 and 11 react like the N-(acetoxy)anilines 20 as "ultimate" carcinogens.Therefore, the activation of aromatic hydroxylamines by O-α-aminoacylation is of similar quality as by O-acetylation.
