Preparação e avaliações biológica e físico-química de novas aminas e amidas aromáticas anfifílicas

Abstract

In this work were carried out the synthesis of novel amphiphilic aromatic amines and amides derived from Tris. The first set was obtained by reductive amination reaction of p- alkyloxybenzadehydes with TRIS. The series of amides was obtained starting from p- akyloxylbenzoic acid: these were converted to the acyl chlorides and treated with TRIS. The methodologies used were simple and all compounds were obtained in satisfactory yields. After purification and characterization through the usual spectroscopic techniques (IR, 1 H NMR, ¹³C NMR and mass spectroscopy), the synthesized compounds were evaluated for their biological properties in vitro. The antimicrobial activity was evaluated against Gram-positive bacteria (ATCC and MRSA), Gram-negative bacteria (ATCC) and fungi of Candida. The anti inflammatory potential was assessed by the ability of the compounds to inhibit nitric oxide production by activated macrophages. Cytotoxicity was assessed by the MTT method. The results showed that only the amines were active in the tests, with minimum inhibitory concentrations comparable or superior to the standards used as control (chloramphenicol and itraconazole), and showed no toxicity in these concentrations. It was possible to establish a good correlation between the lipophilicity of the tested compounds and the antimicrobial activity. The physico-chemical studies are still under going aiming to establish a relationship between the biological activity and the surfactant properties of the new amphiphilic amines.