Novel series of 17β-pyrazolylandrosta-5,16-diene derivatives and their inhibitory effect on 17α-hydroxylase/C17,20-lyase

Zoltán Iványi, Nikoletta Szabó, János Wölfling, Mihály Szécsi, János Julesz, Gyula Schneider

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

The Claisen condensation of 3β-acetoxypregna-5,16-dien-20-one (1) with ethyl formate in the presence of sodium methylate in pyridine is known to lead to 3β-hydroxy-21-hydroxymethylidenepregna-5,16-dien-20-one (2) in good yield. With the methods described for the preparation of the saturated D-ring pyrazolyl series, the reactions of 2 with phenylhydrazine and its p-substituted derivatives in acetic acid resulted in mixtures of two steroidal regioisomers, the 1′-aryl-3′-pyrazolyl-(4a-e) and 1′-aryl-5′-pyrazolyl (5a-e) steroids. Compounds 4a-e are unknown in the literature. The arylpyrazoles produced were tested against 17α-hydroxylase/C 17,20-lyase (P45017α) in vitro and neither of the regioisomers exerted efficient inhibition.

Original languageEnglish
Pages (from-to)1152-1159
Number of pages8
JournalSteroids
Volume77
Issue number11
DOIs
Publication statusPublished - Sep 1 2012

Keywords

  • Claisen condensation
  • P450 inhibitors
  • Regioisomeric 17β-N-phenylpyrazolyl steroids

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Novel series of 17β-pyrazolylandrosta-5,16-diene derivatives and their inhibitory effect on 17α-hydroxylase/C<sub>17,20</sub>-lyase'. Together they form a unique fingerprint.

  • Cite this