Contraceptive agents from cycloaddition reactions of diarylcyclopropenones and diarylthiirene 1,1 dioxides

Article abstract of DOI:10.1021/jm00225a016

The potential for compounds with antifertility activity from the reactions of diphenylcyclopropenone and 2,3 diphenylthiirene 1,1 dioxide with enamines is described. In certain instances, a marked dissociation of antifertility from estrogenic activity was possible. 2 Series were studied extensively, one was stilbene amides and the other stilbene amino ketones. The latter afforded several materials from which, on further biological work up, was singled out compound 21 as a potent antifertility agent in rats and hamsters. The antifertility activity from the reactions of diphenylcyclopropene (1) and 2,3-diphenylthiirene 1,1 dioxide (2) with enamines was investigated in laboratory rodents. A considerable dissociation of antifertility from estrogenic activity was observed in certain instances. Stilbene amides (7) and stilbene aminoketones (8) we re extensively studied. The stilbene aminoketone group provided several materials of which compound 21 was found to be a highly potent antifertility agent. The preparation of the materials is described.