R. Crenshaw, A. T. Jeffries, G. M. Luke
Dec 1, 1971
Citations
0
Influential Citations
28
Citations
Quality indicators
Journal
Journal of medicinal chemistry
Abstract
The syntheses and biological activities of diaryl ethylene derivatives of the general structure type 2 for potential antifertility agents are reported. These compounds have estrogenic and/or estrogen antagonist activities. Compounds of substituted diaryl derivatives of benxo(b)thiophenes benzo(b)furans 1 2-2-benzo thiapyrans and 2 2-1-benzothiapyrans were included. The most active compounds were 6-methoxy-3(p(2-(pyrrolidy)ethoxylphenl)-2-Phenylbenzo(b)thiophene (3m) and 34-dihydro-7-methoxy-3-phenyl-4-hydroxy-4-(p-(2-(1-pyrrolidy) ethoxy)phenyl)-1 2-benxothipyran (11a). A dibenzo(bc) thiepin (20) containing some of the structural features of 11a is also reported. This structural modification resulted in a loss of activity. Both 3m and 11a afford complete protection against pregnancy in rats at doses of .1 mg/kg. The compounds exhibit a rapidly plateauing uterotrophic activity in the rat which fails to approach the maxima seen with known potent estrogens.(Authors modified)