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Molecules 2016, 21(5), 611; doi:10.3390/molecules21050611

Synthesis and in Vitro Antiproliferative Evaluation of C-13 Epimers of Triazolyl-d-Secoestrone Alcohols: The First Potent 13α-d-Secoestrone Derivative

1
Department of Organic Chemistry, University of Szeged, Dóm tér 8, Szeged H-6720, Hungary
2
Department of Pharmacodynamics and Biopharmacy, University of Szeged, Eötvös u. 6, Szeged H-6720, Hungary
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 31 March 2016 / Revised: 28 April 2016 / Accepted: 29 April 2016 / Published: 12 May 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [583 KB, uploaded 12 May 2016]   |  

Abstract

The syntheses of C-13 epimeric 3-[(1-benzyl-1,2,3-triazol-4-yl)methoxy]-d-secoestrones are reported. Triazoles were prepared from 3-(prop-2-inyloxy)-d-secoalcohols and p-substituted benzyl azides via Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). The antiproliferative activities of the products and their precursors were determined in vitro against a panel of human adherent cervical (HeLa, SiHa and C33A), breast (MCF-7, MDA-MB-231, MDA-MB-361 and T47D) and ovarian (A2780) cell lines by means of MTT assays. The orientation of the angular methyl group and the substitution pattern of the benzyl group of the azide greatly influenced the cell growth-inhibitory potential of the compounds. The 13β derivatives generally proved to be more potent than their 13α counterparts. Introduction of a benzyltriazolylmethyl group onto the 3-OH position seemed to be advantageous. One 13α compound containing an unsubstituted benzyltriazolyl function displayed outstanding antiproliferative activities against three cell lines. View Full-Text
Keywords: antiproliferative effect; azide-alkyne cycloaddition; d-secoestrone; triazole antiproliferative effect; azide-alkyne cycloaddition; d-secoestrone; triazole
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Szabó, J.; Jerkovics, N.; Schneider, G.; Wölfling, J.; Bózsity, N.; Minorics, R.; Zupkó, I.; Mernyák, E. Synthesis and in Vitro Antiproliferative Evaluation of C-13 Epimers of Triazolyl-d-Secoestrone Alcohols: The First Potent 13α-d-Secoestrone Derivative. Molecules 2016, 21, 611.

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