Stereocontrolled synthesis of the four possible 3-methoxy and 3-benzyloxy-16-triazolyl-methyl-estra-17-ol hybrids and their antiproliferative activities

Anita Kiss, János Wölfling, Erzsébet Mernyák, Éva Frank, Zsanett Benke, Seyyed Ashkan Senobar Tahaei, István Zupkó, Sándor Mahó, Gyula Schneider

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

The four possible isomers of each of 3-methoxy- and 3-benzyloxyestra-1,3,5(10)-trien-17-ols (5–8 and 9–12) were converted through 16-p-tosyloxymethyl- or 16-bromomethyl derivatives into their 3-methoxy- and 3-benzyloxy-16-azidomethylestra(1,3,5(10)-triene derivatives (13–16 and 17–20). The regioselective Cu(I)-catalyzed 1,3-dipolar cycloaddition of these compounds with different terminal alkynes afforded novel 1,4-disubstituted diastereomers (21a–f, 22a–f, 23a–f, 24a–f and 25a–f, 26a–f, 27a–f, 28a-f). The antiproliferative activities of the structurally related triazoles were determined in vitro with the microculture tetrazolium assay on four malignant human cell lines of gynecological origin (Hela, SiHa, MCF-7 and MDA-MB-231).

Original languageEnglish
Article number108500
JournalSteroids
Volume152
DOIs
Publication statusPublished - Dec 2019

Keywords

  • 1,3-Dipolar cycloaddition
  • 3-Methoxy - and 3-benzyloxy-16-azidomethylestra-1,3,5(10)-triene-17-ols
  • 4′Substituted-steroid triazoles
  • Cytotoxic activity

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Endocrinology
  • Pharmacology
  • Clinical Biochemistry
  • Organic Chemistry

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