A series of rifamycin S derivatives carrying at C(3) an aliphatic side-chain of variable length terminating with a carboxyl has been synthesised; in particular, five of these compounds carry a terminal dipeptide. The aim was to prepare potential bifunctional HIV-1 reverse transcriptase inhibitors, able both to bind at the non-nucleoside inhibitors binding site, through the chromophore rings, and to interfere with the catalytic centre, through the side-chain terminal carboxyl. Some of the compounds display an interesting inhibitory power (IC50 45-60 mu M) In addition, a few of these derivatives have been also tested as potential antibacterial agents, and showed a good level of activity toward Gram-positive bacteria.
Synthesis and activity studies on 3-(carboxyalkylthio)rifamycin S derivatives / L., C., C., M., M., M., A., M.O., Mannina, L., A., B., A., D.C., S., L., F., R.. - In: GAZZETTA CHIMICA ITALIANA. - ISSN 0016-5603. - STAMPA. - 127:(1997), pp. 317-323.
Synthesis and activity studies on 3-(carboxyalkylthio)rifamycin S derivatives
MANNINA, LUISA;
1997
Abstract
A series of rifamycin S derivatives carrying at C(3) an aliphatic side-chain of variable length terminating with a carboxyl has been synthesised; in particular, five of these compounds carry a terminal dipeptide. The aim was to prepare potential bifunctional HIV-1 reverse transcriptase inhibitors, able both to bind at the non-nucleoside inhibitors binding site, through the chromophore rings, and to interfere with the catalytic centre, through the side-chain terminal carboxyl. Some of the compounds display an interesting inhibitory power (IC50 45-60 mu M) In addition, a few of these derivatives have been also tested as potential antibacterial agents, and showed a good level of activity toward Gram-positive bacteria.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
