Two androsterone derivatives as inhibitors of androgen biosynthesis

Abstract

The title compounds, (3R,5S,5′R,8R,9S,10S,13S,14S)-10,13-dimethyl-5′-(2-methylpropyl)tetradecahydro-6′H-spiro[cyclopenta[a]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-spiro[cyclopenta[a]phenanthrene-3,5′-[1,3]oxazolidin-3′-yl]]-4-methylpentanoate, C28H43NO5, (II), possess the typical steroid shape (A–Drings), but they differ in their extraEring. The azalactoneEring in (I) shows a half-chair conformation, while the carbamateEring of (II) is planar. The orientation of theE-ring substituent is clearly established and allows a rationalization of the biological results obtained with such androsterone derivatives.