Contraceptive agents from cycloaddition reactions of diarylcyclopropenones and diarylthiirene 1, 1-dioxides.
The potential for compounds with antifertility activity from the reactions of diphenylcyclopropernone (1) and 2, 3-diphenylthiirene 1, 1-dioxide (2) with enamines is described. In certain instances, a marked dissociation of antifertility from estrogenic activity was possible. Two series were studied extensively, one was stilbene amides (7) and the other stilbene amino ketones (8). The latter series (8) afforded several materials from which, on further biological work-up, was singled out compound 21 as a potent antifertility agent in rats and hamsters.
D000818:Animals; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis*; D003280:Contraceptives, Oral, Synthetic / Q000138:chemical synthesis* / Q000494:pharmacology; D006224:Cricetinae; D003521:Cyclopropanes; D004285:Dogs; D010064:Embryo Implantation / Q000187:drug effects; D005260:Female; D005298:Fertility / Q000187:drug effects; D005313:Fetal Death / Q000139:chemically induced; D005327:Fetal Resorption / Q000139:chemically induced; D009682:Magnetic Resonance Spectroscopy; D009929:Organ Size / Q000187:drug effects; D011247:Pregnancy; D011555:Pseudopregnancy / Q000187:drug effects; D011817:Rabbits; D051381:Rats; D013055:Spectrophotometry, Infrared; D013056:Spectrophotometry, Ultraviolet; D014599:Uterus / Q000187:drug effects
D001643:Bridged Bicyclo Compounds; D001952:Bridged-Ring Compounds; D003280:Contraceptives, Oral, Synthetic; D003521:Cyclopropanes