title: S-, N-, and O-glycosyl derivatives of 2-acetamido-2-deoxy-D-glucose with hydrophobic aglycons as potential chemotherapeutic agents and N-acetyl-beta-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-beta-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 NH2-1 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-beta-D-glucosaminidase from beef liver.
mesh_terms: D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D000230:Adenocarcinoma / Q000188:drug therapy*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D002417:Cattle; D005260:Female; D006596:Hexosaminidases / Q000037:antagonists & inhibitors*; D007202:Indicators and Reagents; D008099:Liver / Q000201:enzymology; D009682:Magnetic Resonance Spectroscopy; D008325:Mammary Neoplasms, Experimental / Q000188:drug therapy*; D051379:Mice; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D006596:Hexosaminidases; D000118:Acetylglucosaminidase