Two androsterone derivatives as inhibitors of androgen biosynthesis.
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, C(26)H(41)NO(3), (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, C(28)H(43)NO(5), (II), possess the typical steroid shape (A-D 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.
Laboratory of Medicinal Chemistry, CHUQ (CHUL)-Research Center and Laval University, Québec, Canada G1V 4G2.
Guy-Bertrand
GB
Djigoue
Michel
M
Simard
Lucie-Carolle
LC
Kenmogne
Donald
D
Poirier
D000726:Androgen Antagonists / Q000737:chemistry* / Q000494:pharmacology*; D000728:Androgens / Q000096:biosynthesis* / Q000737:chemistry*; D000738:Androsterone / Q000031:analogs & derivatives / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D008958:Models, Molecular
D000726:Androgen Antagonists; D000728:Androgens; D000738:Androsterone