Síntese e caracterização de derivados alquilados do 2-aminoetanotiol, potenciais agentes antiparasitários

Abstract

The synthesis, characterization and biological activity evaluation of bioactive molecules constitute an area of great interest in our research group. Aminothiols are a class of molecules used in some therapies such as nephropathic cystinosis, cytoprotection in cancer treatment and use in radiopharmaceuticals. Other biological properties have also been reported in the literature such as antiparasitic and antibacterial activity. In this work, the synthesis of alkylated compounds derived from aminoethanethiol obtained from nucleophilic substitution reaction with the 2-aminoethanethiol hydrochloride reagent is described. The substrates used were: alkyl halides with saturated chains of C-10 and C-12 carbon atoms, substituted benzyl chlorides and iodinated derivatives of adamantane and D-galactose (5 and 8). Were used commercial alkyl halides and for the reaction with the benzyl chlorides were prepared two chlorides (2c and 2d), derived from the respective benzyl alcohols. The hydroxyls from D-galactose were protected to form the product 4. The intermediate compounds 5 and 8 were obtained from nucleophilic substitution by the iodo atom on C-6 carbon for derivative 5 and on carbon C-1 for derivative 8. Compounds derived from aminoethanethiol 1a-1f, 3a-3d, 6, 7 and 10 were obtained from reactions of substrates with 2-aminoethanethiol hydrochloride in the presence of weak base in ethanol. The products obtained had their structures elucidated by analysis of Infrared spectra, 1H and 13C NMR, COSY (1H x 1H) and HSQC (1H X 13C) maps.