A facile access to novel steroidal 17-2′-(1′,3′,4′) -oxadiazoles, and an evaluation of their cytotoxic activities in vitro

Dóra Kovács, Gergo Mótyán, J. Wölfling, Ida Kovács, I. Zupkó, E. Frank

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

Novel types of 17-exo-heterocycles in the Δ5 androstene series carrying an 1,3,4-oxadiazole moiety were efficiently synthesized via aldehyde N-acylhydrazone intermediates, obtained from the microwave-assisted condensation of 3β-hydroxy- or 3β-acetoxyandrost-5-ene-17β- carbaldehyde with different acylhydrazides. The subsequent phenyl iodonium diacetate-induced oxidative cyclization proceeded under mild conditions. The synthesized compounds were subjected to in vitro pharmacological studies to investigate their antiproliferative activities on four malignant adherent cell lines (HeLa, MCF7, A2780 and A431), and exhibited the highest potency against HeLa cells, some of them revealing action comparable to that of the reference agent cisplatin.

Original languageEnglish
Pages (from-to)1265-1268
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume24
Issue number5
DOIs
Publication statusPublished - Mar 1 2014

Fingerprint

Androstenes
Cyclization
Microwaves
HeLa Cells
Aldehydes
Cisplatin
Condensation
Cells
Pharmacology
Cell Line
In Vitro Techniques
1,3,4-oxadiazole

Keywords

  • 1,3,4-Oxadiazoles
  • Antiproliferative
  • Microwave
  • N-Acylhydrazones
  • Steroid

ASJC Scopus subject areas

  • Pharmaceutical Science
  • Drug Discovery
  • Organic Chemistry
  • Molecular Medicine
  • Molecular Biology
  • Clinical Biochemistry
  • Biochemistry

Cite this

A facile access to novel steroidal 17-2′-(1′,3′,4′) -oxadiazoles, and an evaluation of their cytotoxic activities in vitro. / Kovács, Dóra; Mótyán, Gergo; Wölfling, J.; Kovács, Ida; Zupkó, I.; Frank, E.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 24, No. 5, 01.03.2014, p. 1265-1268.

Research output: Contribution to journalArticle

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