title: Stereoselective synthesis of some 17beta-dihydrooxazinyl steroids, as novel presumed inhibitors of 17alpha-hydroxylase-C17,20-lyase.
abstract: 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.
authors.affiliation: Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. wolfling@chem.u-szeged.hu
authors.forename: János
authors.initials: J
authors.lastname: Wölfling
authors.forename: Eva Andrea
authors.initials: EA
authors.lastname: Oravecz
authors.forename: Dóra
authors.initials: D
authors.lastname: Ondré
authors.forename: Erzsébet
authors.initials: E
authors.lastname: Mernyák
authors.forename: Gyula
authors.initials: G
authors.lastname: Schneider
authors.forename: István
authors.initials: I
authors.lastname: Tóth
authors.forename: Mihály
authors.initials: M
authors.lastname: Szécsi
authors.forename: János
authors.initials: J
authors.lastname: Julesz
mesh_terms: D008968:Molecular Conformation; D013237:Stereoisomerism; D013254:Steroid 17-alpha-Hydroxylase / Q000037:antagonists & inhibitors*; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D013260:Steroids, Heterocyclic; D013254:Steroid 17-alpha-Hydroxylase