Synthesis and in Vitro antiproliferative evaluation of C-13 epimers of triazolyl-D-secoestrone alcohols

The first potent 13α-D-secoestrone derivative

Johanna Szabó, Nóra Jerkovics, G. Schneider, J. Wölfling, Noémi Bózsity, Renáta Minorics, I. Zupkó, E. Mernyák

Research output: Contribution to journalArticle

13 Citations (Scopus)

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.

Original languageEnglish
Article number611
JournalMolecules
Volume21
Issue number5
DOIs
Publication statusPublished - May 1 2016

Fingerprint

Azides
multiple docking adapters
alcohols
Alcohols
Derivatives
cultured cells
evaluation
synthesis
Cells
Cell Line
Triazoles
Alkynes
Cycloaddition
Cycloaddition Reaction
Cell growth
cycloaddition
alkynes
breast
Assays
Breast

Keywords

  • Antiproliferative effect
  • Azide-alkyne cycloaddition
  • D-secoestrone
  • Triazole

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis and in Vitro antiproliferative evaluation of C-13 epimers of triazolyl-D-secoestrone alcohols : The first potent 13α-D-secoestrone derivative. / Szabó, Johanna; Jerkovics, Nóra; Schneider, G.; Wölfling, J.; Bózsity, Noémi; Minorics, Renáta; Zupkó, I.; Mernyák, E.

In: Molecules, Vol. 21, No. 5, 611, 01.05.2016.

Research output: Contribution to journalArticle

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