Síntese, caracterização e avaliação biológica de aminoálcoois lipofílicos acoplados a carboidratos, candidatos a novos agentes antituberculose

Abstract

A amines and aminoalcohols are important chemical classes that are present in a large group of synthetic and naturally occurring substances. The presence of alcohol and amine functional groups allow these substances aminoalcohol S,S-ethambutol is a reliable first-line antitubercular chemotherapeutic agent. Glycosylated amines and aminoalcohols are known for their antibacterial activities. This work describes the synthesis of aminoalcohols derived from Darabinose and D-galactose which resulted in the synthesis of fourteen novel compounds. Initially we reported the preparation of six diamines and seven Nalkylated amines with carbon chains of different lengths. The diamines and aminoalcohols thus obtained were coupled to the intermediate 6-O-(2’,3’- epoxypropyl)-1,2:3,4-di-isopropylidene- -D-galactopyranoside that was prepared by classical carbohydrate chemical reactions. Thirteen new compounds were obtained, all in the form of diastereoisomeric mixture. We also obtained an aminoalcohol derived from D-arabinose series. This was prepared by the epóxido opening reaction of methyl 2,3-anydro-5-Obenzyl- -D-lyxofuranoside from the commercial aminoalcohol monoethanolamine. Several aminoalcohols of the D-galactose series were submitted for biological assays in order to evaluate their antibacterial and antitubercular activities and showed promising results.