Potential antifertility agents. 1. Substituted diaryl derivatives of benzo[b]thiophenes, benzo[b]furans, 1H-2-benzothiapyrans, and 2H-1-benzothiapyrans
| Autor: | R. R. Crenshaw, G. Bialy, George M. Luke, A. T. Jeffries, L. C. Cheney |
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| Rok vydání: | 1971 |
| Předmět: |
Male
Time Factors Ethylene Research methodology Thiophenes Structure type Medicinal chemistry Mice chemistry.chemical_compound Health services Testis Drug Discovery Thiophene Animals Organic chemistry Benzopyrans Benzofurans Anticholesteremic Agents Uterus Estrogen Antagonists Prostate Seminal Vesicles Organ Size Rats Cholesterol chemistry Alkoxy group Molecular Medicine Female Gonadotropins Sulfur Contraceptives Oral |
| Zdroj: | Journal of Medicinal Chemistry. 14:1185-1190 |
| ISSN: | 1520-4804 0022-2623 |
| Popis: | 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) |
| Databáze: | OpenAIRE |
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