Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series

Dóra Kovács, Zalán Kádár, Gerg Mótyán, Gyula Schneider, János Wölfling, István Zupkó, Éva Frank

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24 Citations (Scopus)

Abstract

Regioselective 1,3-dipolar cycloadditions of different aryl nitrile oxides to mestranol were carried out to furnish novel steroidal 17α-isoxazoles in good to excellent yields. Copper(I) was found to be an efficient catalyst, accelerating the intermolecular ring-closures and leading exclusively to 3,5-disubstituted isoxazoles. The yields of the cycloadducts, however, were influenced by the substituents on the aromatic moiety of the 1,3-dipoles. Moreover, dehydration of the primary products resulted in the corresponding Δ16,17 exo-heterocyclic derivatives. All the synthesized compounds were subjected to in vitro pharmacological studies of their antiproliferative effects relative to three human malignant cell lines (HeLa, MCF7 and A2780).

Original languageEnglish
Pages (from-to)1075-1085
Number of pages11
JournalSteroids
Volume77
Issue number11
DOIs
Publication statusPublished - Sep 1 2012

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Keywords

  • Cycloaddition
  • Cytotoxic activity
  • Isoxazoles
  • Nitrile oxides

ASJC Scopus subject areas

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

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