ABSTRACT
The synthesis and biological activity of the methyl esters of (+)-12-fluoroPGF2 alpha, (+)-15-epi-12-fluoroPGF2 alpha, (-)-ent-12-flurorPGF2 alpha, and (-)-ent-15-epi-12-fluoroPGF2 alpha are described. Each fluoroprostaglandin has been evaluated from pregnancy interruption in the hamster and smooth-muscle stimulating effects on gerbil colon and hamster uterine strips. All fluoroprostaglandins synthesized were shown to be neither substrates for the 15-hydroxyprostaglandin dehydrogenase nor inhibitors of the enzyme.
Subject(s)
Prostaglandins F, Synthetic/chemical synthesis , Abortifacient Agents, Nonsteroidal/chemical synthesis , Animals , Cricetinae , Female , Gerbillinae , In Vitro Techniques , Models, Molecular , Muscle Contraction/drug effects , Muscle, Smooth/drug effects , Pregnancy , Prostaglandins F, Synthetic/pharmacology , Stereoisomerism , Structure-Activity Relationship , Uterine Contraction/drug effectsABSTRACT
The synthesis and biological evaluation of the methyl esters of (+)-14-fluoroPGF2 alpha, (+)-15-epi-14-fluoroPGF2 alpha, (+)-13(E)-14-fluoroPGF2 alpha, and (+)-13(E)-15-epi-14-fluoroPGF2 alpha are described. Each fluoroprostaglandin has been evaluated for pregnancy interruption in the hamster and smooth-muscle stimulating effects on gerbil colon and hamster uterine strips.
