Analogues of platelet activating factor. 3. Replacement of the phosphate moiety with a sulfonylbismethylene group.
An analogue of platelet activating factor (PAF) in which the phosphate moiety has been replaced with a sulfonylbismethylene group has been prepared. A key step in the synthetic sequence is the preparation of 4-[[3-(dimethylamino)propyl]thio]-1-(hexadecyloxy)-2-butanol via a one-pot reaction involving a sequential Michael addition and reduction. In comparison to racemic C16-PAF, 8 showed no platelet aggregating activity and substantially reduced hypotensive activity.
D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D055598:Chemical Phenomena; D002621:Chemistry; D010710:Phosphates; D010972:Platelet Activating Factor / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology / Q000502:physiology*; D010974:Platelet Aggregation / Q000187:drug effects; D011817:Rabbits; D051381:Rats; D011918:Rats, Inbred SHR; D013329:Structure-Activity Relationship
D010710:Phosphates; D010972:Platelet Activating Factor; C046494:3-((3-(acetyloxy)-4-(hexadecyloxy)butyl)sulfonyl)-N,N,N-trimethyl-1-propanaminium