Preparation of halonitroarenes via diazotization of nitroaromatic amines. Starting materials for the synthesis of aminoarylcysteine derivatives
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Title
Preparation of halonitroarenes via diazotization of nitroaromatic amines. Starting materials for the synthesis of aminoarylcysteine derivativesAuthor (s)
Tutor/Supervisor; University.Department
Moliner Ibáñez, Vicente; Universitat Jaume I. Departament de Química Física i Analítica; Linhart, IgorDate
2017Publisher
Universitat Jaume IAbstract
S-(2-aminoaryl)cysteines are a presumed cysteine adducts formed from mutagenic and
carcinogenic arylamines and nitroarenes. Both arylamines and nitroarenes are
metabolically activated to corresponding arylnitrenium ... [+]
S-(2-aminoaryl)cysteines are a presumed cysteine adducts formed from mutagenic and
carcinogenic arylamines and nitroarenes. Both arylamines and nitroarenes are
metabolically activated to corresponding arylnitrenium ions which can bind to the
nucleophilic sites in biomolecules such as proteins and nucleic acids. When reaction
with cysteine SH groups in proteins such as globin and albumin, arylnitrenium ions
form adducts (Scheme 1). Hydrolytic cleavage of such protein adducts can release S(aminoaryl)cysteines,
which are potentially useful biomarkers of cumulative exposure to
mutagenic and carcinogenic aromatic amines. Such adduct has been recently identified
in globin and plasma proteins of rats dosed with strongly mutagenic 3-
nitrobenzanthrone (Linhart et al., 2017). The aim of this project is to prepare several fluoro- and bromonitroarenes, which will be
further used as starting materials for the synthesis of aminoarylcysteines. Authentic
samples of aminoarylcysteines are needed for toxicological studies on the formation and
elimination of globin adducts formed in vivo in the course of metabolism of mutagenic
and carcinogenic arylamines and nitroarenes. [-]
Description
Treball Final de Grau en Química. Codi: QU0943. Curs acadèmic: 2016/2017.
Type
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- Grau en Química [265]