Neighboring group participation: Part 15. Stereoselective synthesis of some steroidal tetrahydrooxazin-2-ones, as novel presumed inhibitors of human 5α-reductase

János Wölfling, László Hackler, Erzsébet Mernyák, Gyula Schneider, István Tóth, Mihály Szécsi, János Julesz, Pál Sohár, Antal Csámpai

Research output: Article

38 Citations (Scopus)

Abstract

During the alkaline methanolysis of 3β-acetoxy-21-chloromethyl-pregn- 5-ene-20β-N-phenylurethane, and its p-substituted phenyl derivatives, cyclization occurs, in the course of which 17β-[3-(N-phenyl) tetrahydrooxazin-2-on-6-yl]androst-5-en-3β-ol and its p-substituted phenyl derivatives are formed. The cyclization takes place with (N--6) neighboring group participation. Oppenauer oxidation of the 3β-hydroxy-exo- heterocyclic steroids yielded the corresponding Δ4-3- ketosteroids. The structures of the new compounds were proved by IR, 1H and 13C NMR spectroscopy, using up-to-date measuring techniques such as 2D-COSY, HMQC, and HMBC. The inhibitory effects (CI 50) of the Δ4-3-ketosteroids on 5α-reductase were studied.

Original languageEnglish
Pages (from-to)451-460
Number of pages10
JournalSteroids
Volume69
Issue number7
DOIs
Publication statusPublished - júl. 1 2004

ASJC Scopus subject areas

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

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