Synthesis and biological evaluation of the methyl esters of (+)-12-fluoro-13,14-dihydroprostaglandin F2.alpha. and (+)-15-epi-12-fluoro-13,14-dihydroprostaglandin F2.alpha.
- 1 July 1981
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 24 (7) , 839-843
- https://doi.org/10.1021/jm00139a014
Abstract
(+)-12-Fluoro-13,14-dihydroprostaglandin F2.alpha. methyl ester (2a) and (+)-15-epi-12-fluoro-13,14-dihydroprostaglandin F2.alpha. methyl ester (2b) were prepared from the readily available (-)-7-fluorospiro[bicyclo[2.2.1]hept-5-ene2,2''-[1,3]dioxolane]-7-methanol. Fluoroprostaglandins 2a and 2b possess truly significant separations of antifertility activity from smooth-muscle stimulating properties [in hamsters]. The 2a and 2b were totally inert toward the [human] placental 15-hydroxyprostaglandin dehydrogenase.This publication has 3 references indexed in Scilit:
- Fluoroprostaglandins: synthesis and biological evaluation of the methyl esters of (+)-12-fluoro-, (-)-ent-12-fluoro-, (+)-15-epi-fluoro-, and (-)-ent-15-epi-12-fluoroprostaglandin F2.alpha.Journal of Medicinal Chemistry, 1980
- Synthesis and chiroptical characterization of prostacyclin diastereomersProstaglandins, 1980
- Kinetic studies on a 15-hydroxyprostaglandin dehydrogenase from human placentaArchives of Biochemistry and Biophysics, 1976