Carcinogens Aniline derivatives

Various halogenated and nitrated aniline derivatives are used in the manufacture of dyestuffs and carbamate and urea based pesticides. Many of these compounds are suspected to be carcinogenic. 

Preparation of aromatic amines by the reaction of aryl halides with aliphatic and aromatic amines has been regarded as a difficult reaction. Recently a facile synthetic method for aromatic amines by amination of aryl halides has been discovered, and rapid progress has occurred in the Pd-catalyzed reaction of amines with aryl halides [1]. One simple example which shows the usefulness of the new method is cited here. The commercially important arylpiperazines 1 have been synthesized by intramoleular N-alkylation of aniline derivatives with N,N-di-(2-chloroethyl)amine (2), which is highly carcinogenic. Now the amines 3 can be prepared efficiently by coupling aryl iodides, bromides or chlorides with N-substituted piperidines. This example provides a big contribution to synthetic chemistry by the new Pd-catalyzed efficient preparative method for arylamines, which are usefial in medicinal and material chemistry. 

N-Oxidation. (V-oxidation can occur in a number of ways, including hydroxylamine formation, oxime formation, and N-oxide formation, although the latter is primarily dependent on the FMO enzyme. Hydroxylamine formation occurs with a number of amines such as aniline and many of its substituted derivatives. In the case of 2-acetylaminofluorene the product is a potent carcinogen, and thus the reaction is an activation reaction (Figure 7.6). 

As mentioned earlier (Section IV. E), single-ring aromatic amines such as o-toluidine (24) exhibit pronounced carcinogenic properties. When the dimethyl derivative of aniline, (V,iV-dimethylaniline (31), was fed to Fischer 344 rats and B6C3FT mice, splenic... 

Hecht SS (2003) Carcinogen derived biomarkers applications in studies of human exposure to secondhand tobacco smoke. Tob Control 13 48-56. doi 10.1136/tc.2002.002816 Hinteregger C, Loidl M, Streichsbier F (1992) Characterization of isofunctional ring cleaving enzymes in aniline and 3-chloroaniline degradation by Pseudomonas acidovorans CA28. FEMS Microbiol Lett 97 261-266. http //www.doi.oig/10.1016/0378-1097(92)90346-P Hodne O, Boufatit M, Khouider A (2004) Use of montmorillonite clays as adsorbents of hazardous pollutants. Desalination 167 141—145... 

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