Synthesis and biological evaluation of the methyl esters of (+)-12-fluoro-13,14-dihydroprostaglandin F2alpha and (+)-15-epi-12-fluoro-13,14-dihydroprostaglandin F2alpha.
(+)-12-Fluoro-13,14-dihydroprostaglandin F2alpha methyl ester (2a) and (+)-15-epi-12-fluoro-13,14-dihydroprostaglandin F2alpha methyl ester (2b) were prepared from the readily available (-)-7-fluorospiro[bicyclo[2.2.1]hept-5-ene-2,2'-[1,3]dioxolane]-7-methanol (3). Fluoroprostaglandins 2a and 2b possess truly significant separations of antifertility activity from smooth-muscle stimulating properties. In addition, our studies showed that 2a and 2b were totally inert toward the placental 15-hydroxyprostaglandin dehydrogenase.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003280:Contraceptives, Oral, Synthetic; D006224:Cricetinae; D005260:Female; D005849:Gerbillinae; D006911:Hydroxyprostaglandin Dehydrogenases / Q000378:metabolism; D066298:In Vitro Techniques; D009119:Muscle Contraction / Q000187:drug effects; D009130:Muscle, Smooth / Q000187:drug effects; D011461:Prostaglandins F, Synthetic / Q000138:chemical synthesis* / Q000494:pharmacology
D003280:Contraceptives, Oral, Synthetic; D011461:Prostaglandins F, Synthetic; D006911:Hydroxyprostaglandin Dehydrogenases