A NEW CLASS OF POTENT ANTIPROLIFERATIVE GLYCOLIPIDS

The synthesis and biological activities of a new class of antiproliferative glycolipids with an unexpected broad spectrum of activity, including a human multidrug resistant cell line, are described. Chemically these compounds are glycolipids derived from N-acetyl-D-glucosamine and glycyrrhetinic acid (beta-aglycone). Peptidation of the glucoacids allyl 3-beta-[[2-acetamido-3-O-[(R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranosyl]oxy]-11-oxo-12-oleanen-30-oate and (R,S)-2-methoxy-3-(octadecyloxy)propyl-2-acetamido-3-O-[(R)-1-carboxyethyl]-2-deoxy-4,6-O-isopropylidene-beta-D-glucopyranoside was successfully achieved after activation with O-benzotriazolyl-N,N,N',N'-tetramethyluronium hexafluorophosphate.