Síntese e caracterização de derivados da L-fenilalanina e L-tirosina alinhada à “Química Verde” e avaliação da toxicidade

Abstract

The majority of drugs currently found in modern therapy are of synthetic origin, leading research groups to be constantly looking for new drug candidates. Syntheses and processes conducted with a view to less aggression to the environment are currently gaining ground in academic and industrial circles, in line with the principles of “Green Chemistry”. This work was carried out following this purpose, in which the substances N-(L-phenylalaninyl)- benzamide (P1) and N-(L-tyrosinyl benzoate)-benzamide (P2) were prepared through benzoylation reactions of the starting amino acids L-phenylalanine and L-tyrosine, by the classic Schotten-Baumann method, in aqueous medium and at room temperature. The products were purified by recrystallization and characterized by melting point, thin layer chromatography (TLC) and ultraviolet-visible (UV-VIS) and infrared (IR) spectroscopies. Qualitative antioxidant activities with the diphenylpicrillidrazil radical (DPPH) and of toxic potential against Artemia salina Leach larvae were also investigated. Only P1 indicated significant antioxidant activity. The toxicity test of the products proved to be non-toxic, according to the median lethal concentration values (LC50) obtained. Despite the low yields obtained in the reactions, the characterizations signal for the success of the syntheses of P1 and P2, in a synthetic economic strategy, fast and with low environmental impact.