S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxy- d-glucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-β- d-glucosaminidase inhibitors

Abstract

S-, N-, and O-Glycosyl derivatives of 2-acetamido-2-deoxy- d-glucose with hydrophobic aglycons have been obtained as potential, plasma-membrane active agents. 2-Acetamido-3,4,6-tri- O-acetyl-2-deoxy-1-thio-β- d-glucopyranose ( 6) was converted into benzyl, diphenylmethyl, triphenylmethyl, and other thioglycosides. Acylation of 6 gave adamantoyl and haloacetyl derivatives. A similar series of N- and O-glycosyl derivatives was obtained from the corresponding NH 2-1 and OH-1 analogs of 6, such as O- and N-dinitrophenyl, O- and N-adamantoyl, and N-4-methylbenzylidene derivatives. Several N-and S-glycosyl derivatives were found to inhibit mouse mammary adenocarcinoma (TA3) cells in vitro as well as N-acetyl-β- d-glucosaminidase from beef liver.