1974 Volume 22 Issue 5 Pages 1151-1158
1-N-[(S)-4-Amino-2-hydroxybutyryl]-neamine (3) derived from butirosin, an aminoglycoside antibiotic, has been chemically modified in its amide side chain. The N-benzenesulfonyl derivative (5) was hydrazinolysed and the resulting amine (6) was reacylated with another amino and/or hydroxy carboxylic acid. Removal of benzenesulfonyl groups were carried out with sodium in liquid ammonia, giving several kinds of analogues. In addition, an hydroxy epimer (31) and amino varients (25 and 30) in the α-position of the amide side chain of 3 were prepared starting from tetra-N-mono-O-benzenesulfonyl derivative (23). Antibacterial activity of these analogues were tested and discussed.
