Synthesis and antitubercular activities of bis-glycosylated diamino alcohols

Conjugate addition of diamines to glycosyl olefinic esters la and 1b followed by reduction of resulting bis-glycosyl beta-amino esters (2-7 and 14-19) with lithium aluminium hydride led to the respective glycosyl amino alcohols (8-13 and 20-25) in moderate to good yields. All the compounds were evaluated for antitubercular activity against Mycobacterium tuberculosis H37Ra and H(37)Rv. Few of the compounds exhibited antitubercular activity with MIC as low as 6.25-3.12 mu g/mL in virulent and avirulent strains. Compound 13 was found to be active against MDR strain and showed mild protection in mice. (c) 2005 Elsevier Ltd. All rights reserved.