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Molecules 2011, 16(6), 4786-4806; doi:10.3390/molecules16064786
Article

Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives

1,* , 1, 1, 1, 2, 2, 3,4 and 1,*
1 Department of Organic Chemistry, University of Szeged, Dóm tér 8, H-6720 Szeged, Hungary 2 Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary 3 Faculty of Engineering, University of Szeged, Moszkvai krt. 5-7, H-6725 Szeged, Hungary 4 Fumizol Ltd., Moszkvai krt. 5-7, H-6725 Szeged, Hungary
* Authors to whom correspondence should be addressed.
Received: 12 May 2011 / Revised: 2 June 2011 / Accepted: 6 June 2011 / Published: 9 June 2011
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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.
Keywords: click chemistry; steroid azides; triazoles; tetrazoles; CuAAC click chemistry; steroid azides; triazoles; tetrazoles; CuAAC
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
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Kádár, Z.; Kovács, D.; Frank, É.; Schneider, G.; Huber, J.; Zupkó, I.; Bartók, T.; Wölfling, J. Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives. Molecules 2011, 16, 4786-4806.

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