Steroidal Aldosterone Antagonists. IV¹

Studies directed towards a mechanistic evaluation of inactivation of aromatase by the suicide substrates androsta-1,4-diene-3,17-diones and its 6-ene derivatives

“…Solutions of 19-substituted ADs (7, 0.18 mmol), chloranil (66 mg, 0.26 mmol), and p-toluenesulfonic acid (p-TsOH; 1.5 mg, 8 mol) in dry xylene (5 ml) were separately heated under reflux for 5 h under N 2 atmosphere [43]. After this time, the reaction mixture were subjected to a column of silica gel (12 g).…”

Steroidal Mineralocorticoid Receptor Antagonists: Synthesis and Biology

“…With this goal 7α,9,11‐ene spirolactone derivatives 7 a–f were prepared from known triene 6 (Δ9,11‐canrenone) as outlined in Scheme . Reaction of 6 with the appropriate Grignard reagent gave the required 7α‐methyl and 7α‐ n ‐propyl derivatives 7 a, b following purification . 7α‐Thioethers 7 c–e were prepared by treatment of 6 with the corresponding sodium thiolate prepared in situ .…”

Fluorine-Containing Steroids

“…Most active was 3-(3,1l-dioxo-9a-fl.uoro-17p-hydroxy-4-androsten-17a-yl) propanoic acid lactone, which had about 5 times the subcutaneous and 100 times the oral blocking potency against desoxycorticosterone action in adrenalectomized rats as the basic structure, 3-(3-oxo-17p-hydroxy-4-androsten-17a-yl) propanoic acid lactone. Alterations of the above-mentioned 9a-fl.uoro lactone by addition of other substituents, including the 6a-fl.uoro group (BROWN and BURTNER, 1963) or 2a-methyl group (ATWATER et al, 1961) resulted in reduced mineralocorticoid-blocking activity.…”