Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro

Éva Frank; Judit Molnár; István Zupkó; Zalán Kádár; János Wölfling

doi:10.1016/j.steroids.2011.05.002

Synthesis of novel steroidal 17α-triazolyl derivatives via Cu(I)-catalyzed azide-alkyne cycloaddition, and an evaluation of their cytotoxic activity in vitro

Steroids. 2011 Sep-Oct;76(10-11):1141-8. doi: 10.1016/j.steroids.2011.05.002. Epub 2011 May 10.

Authors

Éva Frank¹, Judit Molnár, István Zupkó, Zalán Kádár, János Wölfling

Affiliation

¹ Department of Organic Chemistry, University of Szeged, Dóm tér 8., H-6720 Szeged, Hungary. frank@chem.u-szeged.hu

PMID: 21600229
DOI: 10.1016/j.steroids.2011.05.002

Abstract

Regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of steroidal 17α-azides with different terminal alkynes afforded novel 1,4-disubstituted triazolyl derivatives in good yields in both the estrone and the androstane series. The antiproliferative activities of the structurally related triazoles were determined in vitro on three malignant human cell lines (HeLa, MCF7 and A431), with the microculture tetrazolium assay.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Azides / chemistry*
Catalysis
Cell Line, Tumor
Cell Proliferation / drug effects
HeLa Cells
Humans
Magnetic Resonance Spectroscopy
Steroids / chemical synthesis*
Steroids / chemistry*
Steroids / pharmacology
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology

Substances

Alkynes
Azides
Steroids
Triazoles