Síntese de amino-álcoois derivados de carboidratos, potenciais agentes antituberculose

Abstract

Ethambutol (amino-alcohol) is one of the few long-known and reliable first-line antitubercular chemotherapeutic agents. Glycosylated amino-alcohol and amines are known for their antimycobacterial activity. This work describes the synthesis of amino-alcohols derived from D-galactose, D-arabinose and D-glucose which resulted in eighteen new compounds. Initially we report the preparation of several N-alkyl amino-alcohols with alkyl chains of different lengths. The amino-alcohols obtained were condensed with iodo or tosyl derivatives of D-arabinose, D-galactose or D-glucose. For the preparation of the tosyl derivative of D-arabinose, the lates was initially treated with methanol under acidic conditions (Amberlite IR-120) leading to methyl-α-D-arabinofuranoside, wich was subsequently tosylated at the C-5 position, furnishing 6-O-tosyl-methyl-α-Darabinofuranoside. The iodo or tosyl derivatives of D-galactose and D-glucose had previously been prepared by classical sugar reactions. The final compounds were obtained via substitution of the tosyl group or iodine atom of these derivatives by commercial amino-alcohols (ethanolamine, 3-amino-propanol, 2-amino-2-methyl-propanol and diethanolamine) or by the previously prepared lipophilic amino-alcohols. Several of these compounds have been submitted for biological assays in order to evaluate their imunosuppressive and antitubercular activities. These compounds were characterized by infrared spectroscopy, 1H and 13C NMR, mass spectroscopy and αD.