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

János Wölfling, Éva Andrea Oravecz, Dóra Ondré, Erzsébet Mernyák, Gyula Schneider, István Tóth, Mihály Szécsi, János Julesz

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30 Citations (Scopus)

Abstract

17β-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-3β-ols substituted in position 17β with dihydrooxazine residues. The inhibitory effects of these compounds on rat testicular C17,20-lyase were investigated with an in vitro radioincubation technique.

Original languageEnglish
Pages (from-to)809-816
Number of pages8
JournalSteroids
Volume71
Issue number9
DOIs
Publication statusPublished - Sep 1 2006

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Keywords

  • C-lyase activity
  • Heterocyclic steroids
  • Schmidt reaction

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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