Agents for alkylating steroid hormone receptors. 3. Omega-substituted esters of 17-alpha-hydroxyprogesterone.

Article abstract of DOI:10.1002/jps.2600600722

The synthesis and Clauberg activity of the 8-carbomethoxyoctanoate (IIe), 9-carbomethoxynonanoate (IIf), 9-carboethoxynonanoate (IIg), 9-carbo-tert-butoxynonanoate (IIh), 8-carboxyoctanoate (IIId), 9-oxo-10-diazodecanoate (IVd), 5-oxo-6-hydroxyhexanoate (Va), and 6-oxo-7-hydroxyheptanoate (Vb) esters of 17-alpha-hydroxyprogesterone are reported in this article. Esters IIa-IIe and IIe-IIh were tested by the McPhail modification of the Clauberg assay. The progestational activity increased with chain length for the glutarate ester IIa through the pimelate ester IIe. It then decreased slightly for the azelate ester IIe and decreased further for the methyl and tert-butyl sebacates IIf and IIh.