Synthesis of 1-O-alkyl-2-O-methyl-glycerophospholipids with potential antitumor activity
Alunni-Bistocchi, G.; Orvietani, P.L.; Ricci, A.; Binaglia, L.; Orlando, M.; Orlando, P.
Farmaco 45(5): 499-509
1990
ISSN/ISBN: 0014-827X PMID: 2222722 Document Number: 360540
Some synthetic alkyl-lysophospholipid analogs have been described as a new class of immunopotentiating and antitumor agents. Among them, 1-O-octadecyl-2-O-methyl-rac-glycero-3-phosphocholine has been reported to possess the highest antitumor activity. A new method for the synthesis of this compound and of the ethanolamine- and serine-containing analog is reported. 1-Alkyl-2-methyl-rac-glycerol, prepared from 1,2-isopropylidene-glycerol, is phosphorylated and the intermediate is condensed either with N-t-BOC-protected ethanolamine or with N-t-BOC-protected serine benzhydryl ester. The choline-derivative is obtained by methylation with CH3I of the ethanolamine derivative. The same synthetic sequence has been used also for synthesizing compounds unsaturated at the fatty alkyl chain in position 1 of the glycerol moiety. Preliminary observation are reported on the selective cytolytic action of the compounds on a tumor cell line.