Stereoselective synthesis of some 17beta-dihydrooxazinyl steroids, as novel presumed inhibitors of 17alpha-hydroxylase-C17,20-lyase

János Wölfling; Eva Andrea Oravecz; Dóra Ondré; Erzsébet Mernyák; Gyula Schneider; István Tóth; Mihály Szécsi; János Julesz

doi:10.1016/j.steroids.2006.05.011

Stereoselective synthesis of some 17beta-dihydrooxazinyl steroids, as novel presumed inhibitors of 17alpha-hydroxylase-C17,20-lyase

Steroids. 2006 Sep;71(9):809-16. doi: 10.1016/j.steroids.2006.05.011. Epub 2006 Jun 30.

Authors

János Wölfling¹, Eva Andrea Oravecz, Dóra Ondré, Erzsébet Mernyák, Gyula Schneider, István Tóth, Mihály Szécsi, János Julesz

Affiliation

¹ Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary. wolfling@chem.u-szeged.hu

PMID: 16814336
DOI: 10.1016/j.steroids.2006.05.011

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Molecular Conformation
Stereoisomerism
Steroid 17-alpha-Hydroxylase / antagonists & inhibitors*
Steroids, Heterocyclic / chemical synthesis*
Steroids, Heterocyclic / pharmacology*

Substances

Steroids, Heterocyclic
Steroid 17-alpha-Hydroxylase