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

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-azidom...

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Autores principales: Kádár, Zalán, Kovács, Dóra, Frank, Éva, Schneider, Gyula, Huber, Judit, Zupkó, István, Bartók, Tibor, Wölfling, János
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2011
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264172/
https://www.ncbi.nlm.nih.gov/pubmed/21659965
http://dx.doi.org/10.3390/molecules16064786
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author Kádár, Zalán
Kovács, Dóra
Frank, Éva
Schneider, Gyula
Huber, Judit
Zupkó, István
Bartók, Tibor
Wölfling, János
author_facet Kádár, Zalán
Kovács, Dóra
Frank, Éva
Schneider, Gyula
Huber, Judit
Zupkó, István
Bartók, Tibor
Wölfling, János
author_sort Kádár, Zalán
collection PubMed
description 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.
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spelling pubmed-62641722018-12-10 Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives Kádár, Zalán Kovács, Dóra Frank, Éva Schneider, Gyula Huber, Judit Zupkó, István Bartók, Tibor Wölfling, János Molecules Article 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. MDPI 2011-06-09 /pmc/articles/PMC6264172/ /pubmed/21659965 http://dx.doi.org/10.3390/molecules16064786 Text en © 2011 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Kádár, Zalán
Kovács, Dóra
Frank, Éva
Schneider, Gyula
Huber, Judit
Zupkó, István
Bartók, Tibor
Wölfling, János
Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title_full Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title_fullStr Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title_full_unstemmed Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title_short Synthesis and In Vitro Antiproliferative Activity of Novel Androst-5-ene Triazolyl and Tetrazolyl Derivatives
title_sort synthesis and in vitro antiproliferative activity of novel androst-5-ene triazolyl and tetrazolyl derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6264172/
https://www.ncbi.nlm.nih.gov/pubmed/21659965
http://dx.doi.org/10.3390/molecules16064786
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