Synthesis and Biological Activity of Fluorine-Modified Platelet Activating Factors

Abstract

Fluorine-modified acetyl glyceryl ether phosphorylcholines (platelet activating factors; PAFs) were efficiently synthesized in an enantioselective manner by the coupling of a D-threitol.derivative with fluorinated long-chain alkoxy methanesulfonates. The introduction of a trifluoromethyl group at the terminal of the alkyl ether chain decreased the hypotensive activity and platelet activation considerably. As the number of fluorine atoms in the alkyl ether chain was increased, both activities were gradually restored, but no selective agonist was obtained from among the fluorinated PAFs.