Synthesis and evaluation for uterotrophic and antiimplantation activities of 2-substituted estradiol derivatives.
Two novel series of 2-substituted estradiol derivatives have been synthesized and evaluated for uterotrophic and antiimplantation activities. Among the compounds tested in the rat, 2-acetylestradiol 17 beta-acetate (1), 2-(3'-dimethylamino-1'-propionyl)estradiol 3,17 beta-diacetate (7), 2-(3'-diethylamino-1'-propionyl)estradiol 3,17 beta-diacetate (8), 2-(3'-piperidino-1'-propionyl)estradiol 3,17 beta-diacetate (9), 1'-(2-estradiol 3,17 beta-diacetate-3'-diethylaminopropionyl thiosemicarbazone (12), and 1'-(2-estradiol 3,17 beta-diacetate)-3'-morpholinopropionyl thiosemicarbazone (14) displayed estrogenic activity. At dosages of 4 microliters/rat/day, none of the tested compounds elicited antiimplantation activity. All compounds shared a similar characteristic: nuclear substitution at the C-2 position of the steroid nucleus, a property previously thought to be markedly inhibitory for estrogenic activity.
AboulWafa
O M
OM
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Alexandria, Egypt.
Mohy el-Din
M M
MM
Mohsen
A
A
Omar
M E
ME
D000818:Animals; D010064:Embryo Implantation / Q000187:drug effects*; D004958:Estradiol / Q000031:analogs & derivatives* / Q000494:pharmacology; D005260:Female; D009682:Magnetic Resonance Spectroscopy; D009929:Organ Size / Q000187:drug effects; D051381:Rats; D013329:Structure-Activity Relationship; D014599:Uterus / Q000187:drug effects*
D004958:Estradiol