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Two androsterone derivatives as inhibitors of androgen biosynthesis
Authors:Guy‐Bertrand Djigoue  Michel Simard  Lucie‐Carolle Kenmogne  Donald Poirier
Abstract:The title compounds, (3R,5S,5′R,8R,9S,10S,13S,14S)‐10,13‐dimethyl‐5′‐(2‐methylpropyl)tetradecahydro‐6′H‐spirocyclopentaa]phenanthrene‐3,2′‐1,4]oxazinane]‐6′,17(2H)‐dione, C26H41NO3, (I), and methyl (2R)‐2‐(3R,5S,8R,9S,10S,13S,14S)‐10,13‐dimethyl‐2′,17‐dioxohexadecahydro‐3′H‐spirocyclopentaa]phenanthrene‐3,5′‐1,3]oxazolidin‐3′‐yl]]‐4‐methylpentanoate, C28H43NO5, (II), possess the typical steroid shape (AD rings), but they differ in their extra E ring. The azalactone E ring in (I) shows a half‐chair conformation, while the carbamate E ring of (II) is planar. The orientation of the E‐ring substituent is clearly established and allows a rationalization of the biological results obtained with such androsterone derivatives.
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