Synthesis of D-ring-substituted (5′R)- and (5′S)-17β- pyrazolinylandrostene epimers and comparison of their potential anticancer activities

Zoltán Iványi, Nikoletta Szabó, Judit Huber, János Wölfling, István Zupkó, Mihály Szécsi, Tibor Wittmann, Gyula Schneider

Research output: Contribution to journalArticle

43 Citations (Scopus)

Abstract

Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17β-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C 17,20- lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared.

Original languageEnglish
Pages (from-to)566-574
Number of pages9
JournalSteroids
Volume77
Issue number5
DOIs
Publication statusPublished - Apr 1 2012

Keywords

  • Aldol condensation
  • Anticancer activities
  • Epimers
  • Hydrazine
  • Pregnenolone
  • Pyrazoline

ASJC Scopus subject areas

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

Fingerprint Dive into the research topics of 'Synthesis of D-ring-substituted (5′R)- and (5′S)-17β- pyrazolinylandrostene epimers and comparison of their potential anticancer activities'. Together they form a unique fingerprint.

  • Cite this