Collect. Czech. Chem. Commun. 1984, 49, 2942-2947

Preparation and synandrogenic activity of 17β-hydroxy-4,5-seco-5-androsten-3-one

Luboslav Stárkaa, Alexander Kasalb, Marie Bičíkováa and Richard Hampla

a Research Institute of Endocrinology, 116 94 Prague 1
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Acylation of the sodium salt of dimethyl sulfoxide with methyl 17β-benzoyloxy-A-nor-3,5-seco-5-androsten-3-oate (I) gave the corresponding sulfoxide II which was desulfurated with aluminium amalgam to 17β-hydroxy-4,5-seco-5-androsten-3-one (IV). In vitro and in vivo assays of compound IV have shown that in contrast to antiandrogenic 4,5-seco derivatives V - VIII it has a synandrogenic activity.