Synthesis and in vitro antiproliferative activity of novel androst-5-ene triazolyl and tetrazolyl derivatives

Zalán Kádár, Dóra Kovács, E. Frank, G. Schneider, Judit Huber, I. Zupkó, T. Bartók, J. Wölfling

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

A straightforward and reliable method for the regioselective synthesis of steroidal 1,4-disubstituted triazoles and 1,5-disubstituted tetrazoles via copper(I)-catalyzed cycloadditions is reported. Heterocycle moieties were efficiently introduced onto the starting azide compound 3β-acetoxy- 16β-azidomethylandrost-5-en-17β-ol through use of the "click" chemistry approach. The antiproliferative activities of the newly-synthesized triazoles were determined in vitro on three human gynecological cell lines (HeLa, MCF7 and A2780) using the microculture tetrazolium assay.

Original languageEnglish
Pages (from-to)4786-4806
Number of pages21
JournalMolecules
Volume16
Issue number6
DOIs
Publication statusPublished - Jun 2011

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tetrazoles
Triazoles
cycloaddition
cultured cells
Tetrazoles
Click Chemistry
chemistry
Derivatives
copper
Azides
Cycloaddition
Cycloaddition Reaction
synthesis
Copper
Assays
Cells
Cell Line
In Vitro Techniques

Keywords

  • Click chemistry
  • CuAAC
  • Steroid azides
  • Tetrazoles
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and in vitro antiproliferative activity of novel androst-5-ene triazolyl and tetrazolyl derivatives. / Kádár, Zalán; Kovács, Dóra; Frank, E.; Schneider, G.; Huber, Judit; Zupkó, I.; Bartók, T.; Wölfling, J.

In: Molecules, Vol. 16, No. 6, 06.2011, p. 4786-4806.

Research output: Contribution to journalArticle

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AU - Schneider, G.

AU - Huber, Judit

AU - Zupkó, I.

AU - Bartók, T.

AU - Wölfling, J.

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