Stereoselective synthesis of some 17beta-dihydrooxazinyl steroids, as novel presumed inhibitors of 17alpha-hydroxylase-C17,20-lyase.
17beta-Dihydrooxazinyl steroids 5a-l and 6a-l were synthetized. The acid-catalyzed reactions of 21-azidomethyl-20-hydroxy- and 21-hydroxymethyl-20-azidosteroids with substituted aromatic aldehydes led to the formation of androst-5-en-3beta-ols substituted in position 17beta with dihydrooxazine residues. The inhibitory effects of these compounds on rat testicular C(17,20)-lyase were investigated with an in vitro radioincubation technique.
Wölfling
János
J
Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. wolfling@chem.u-szeged.hu
Oravecz
Eva Andrea
EA
Ondré
Dóra
D
Mernyák
Erzsébet
E
Schneider
Gyula
G
Tóth
István
I
Szécsi
Mihály
M
Julesz
János
J
D008968:Molecular Conformation; D013237:Stereoisomerism; D013254:Steroid 17-alpha-Hydroxylase / Q000037:antagonists & inhibitors*; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology*
D013260:Steroids, Heterocyclic; D013254:Steroid 17-alpha-Hydroxylase