Antiprogestational agents. The synthesis of 7-alkyl steroidal ketones with anti-implantational and antidecidual activity.
A series of 7alpha- and 7beta- alkyl derivatives of steroidal 4-en- and 5-en-3-ones were prepared by 1,6-conjugate addition of organocopper reagents to various steroidal 4,6-dien-3-ones of the androstane, estrane and gonane series. Biological study of these and related compounds revealed that 17beta-hydroxy-7alpha-methyl-5-androsten-3-one (2), 17beta-hydroxy-7alpha-methyl-5-estren-3-one acetate and 17beta-hydroxy-7alpha-methyl-4-estren-3-one acetate had significant anti-implantational and antidecidual activities. The contragestative effects were associated with the latter anti-hormonal properties, and not with the androgenicity of these compounds.
D000737:Androstenols / Q000494:pharmacology; D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D003281:Contraceptives, Postcoital; D003283:Contraceptives, Postcoital, Synthetic; D006224:Cricetinae; D047108:Embryonic Development; D004963:Estrenes / Q000494:pharmacology; D005260:Female; D007664:Ketosteroids / Q000138:chemical synthesis / Q000494:pharmacology; D008297:Male; D008745:Methylation; D008777:Methyltestosterone / Q000494:pharmacology; D011247:Pregnancy; D013237:Stereoisomerism
D000737:Androstenols; D003281:Contraceptives, Postcoital; D003283:Contraceptives, Postcoital, Synthetic; D004963:Estrenes; D007664:Ketosteroids; D008777:Methyltestosterone