Journal of Medicinal Chemistry p. 788 - 795 (1985)
Update date:2022-08-05
Topics:
Marsh, David A.
Brodie, Harry J.
Garrett, Wesley
Tsai-Morris, Chon-Hwa
Brodie, Angela M. H.
The synthesis and biological evaluation of androstenedione derivatives as inhibitors of estrogen biosynthesis are described.The results show that 4-hydroxy analogues are among the most potent in vitro inhibitors of the series.Esterification of the 4-hydroxy steroids generally reduced activity.Further conjugation of the 3-keto 4-ene system to give 4-hydroxy-4,6-androstadiene-3,17-dione caused more rapid inactivation of aromatase in rat ovarian microsomes than 4-hydroxyandrostenedione.Some compounds exhibited differences in activity when tested for inhibition of human placental microsomes vs. rat ovarian microsomes.The 4-hydroxyandrostenedione derivatives and their nonbulky esters were generally more potent in vitro and in vivo inhibitors than other substituted steroids in the series.Several of the synthesized compounds markedly reduce (50-81percent) estrogen levels in rats on proestrus and/or had antifertility action.To date, none of the compounds surpassed the in vivo inhibitory action of 4-hydroxy-4-androstene-3,17-dione or its 4-acetate derivative.
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