In the search for aldosterone antagonists with an optimal activity profile, twelve 9cc,ll-epoxy-steroids were prepared and compared with their 9a, llcc-unsubstituted analogues in terms of steroid receptor binding in vitro and electrolyte excretion in vivo. Substitution of the parent structures by an epoxy group at positions 9a,ll resulted in marginal effects on mineralocorticoid receptor binding and electrolyte excretion, but greatly reduced androgen and gestagen receptor binding. This finding is reflected in the largely lacking unwanted anti-androgenic and gestagenic side effects in animal models of the three most interesting 9cc,1l-epoxy-spirolactones 4(CGP 33 033), lS(CGP 29245), and 25(CGP 30083).
Radical-induced Intramolecular 1,6Transfer of a Formyl Group
SummaryA further example of a radical-induced intramolecular shift of a functional group in steroids is described. In analogy to the sequence leading to the 1,4-transfer of cyano groups [3], llp-nitrite photolysis was used to generate the appropriate C (1 8) radical in the 20-hydroxy-1 1/3-nitrosyloxy-pregnene-2 I -a1 6 . Intramolecular addition of the radical center to the double-bond of the spacially adjacent aldehyde function, followed by fragmentation of the intermediate cyclic alkoxy radical and subsequent oxidation lead directly to the rearranged 18-formyl compound 10.
Drei unabhängige Synthesen der Titelverbindung (V), die gestagene und ovulationshemmende Aktivität besitzt, werden beschrieben: 1. Umwandlung der bereits vorgebildeten Cz‐Einheit am C(13) von (I), 2. direkter.
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