Synthesis of Glycosylrifamycins, a new type of semisynthetic rifamycins

Abstract

(25.1V.96)Glycosylrifamycins, a new type of semisynthetic rifamycin derivatives, can be easily obtained by reaction of 3-(2-aminoethylthio)rifamycin SV (2) with a glycosyl compound carrying a coupling group, such as isothiocyanate or carboxy. We prepared 0-acetylated and free glucopyranosyl and arabinopyranosyl derivatives of rifamycin S and SV (see 3-10), Additionally, derivatives with D-saccharo-1 ,Clactone and with shikimic acid were obtained (see 11-15). Glycosylrifamycins show an interesting inhibitory power on Gram-positive bacteria (Tuble).Introduction. -The appearence of new infectious diseases such as AIDS and the arise of drug resistance in previously sensitive microorganisms, as it is occurring with tuberculosis, prompted the search for new chemotherapeutics and antibiotics.The rifamycins [I] belong to a family of antibiotics highly active on Gram-positive bacteria and on mycobacteria. The lead rifamycin, rifamycin SV ( = rifamycin;