title: N-(substituted-phenyl)-D-glycopyranosylamines and their O-acetyl derivatives as potential modifiers of the formation of glycosaminoglycans.
abstract: D-Arabinosyl, D-ribosyl, D-glucosyl, D-galactosyl, D-mannosyl, and L-rhamnosyl N-glycosides of p-aminobenzoic acid and their O-acetyl derivatives have been synthesized, and their ability to (a) inhibit the replication of cultured B16 melanoma cells and (b) modify the synthesis of glycosaminoglycans by these neoplastic cells have been evaluated. The most cytotoxic compound of the series was N-(p-carboxyphenyl)-2,3,4-tri-O-acetyl-D-arabinopyranosylamine (8), which produced 50% inhibition of cellular proliferation at a concentration of 4 microM; a number of other compounds were relatively cytotoxic, causing 50% inhibition of cell replication at levels of 18 to 49 microM. These effects were not due to modification of glycosaminoglycan biosynthesis, since these compounds were ineffective as inhibitors or initiators of the formation of these macromolecules.
mesh_terms: D000617:Aminoglycosides / Q000138:chemical synthesis* / Q000627:therapeutic use; D000818:Animals; D002455:Cell Division / Q000187:drug effects; D006025:Glycosaminoglycans / Q000096:biosynthesis*; D008545:Melanoma / Q000188:drug therapy
chemical_list: D000617:Aminoglycosides; D006025:Glycosaminoglycans