Lewis acid-induced intramolecular access to novel steroidal ring D-condensed arylpyrazolines exerting in vitro cell-growth-inhibitory effects

Gergő Mótyán, István Zupkó, Renáta Minorics, Gyula Schneider, János Wölfling, Éva Frank

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

Novel androstenoarylpyrazolines were synthesized stereoselectively by the BF3-induced intramolecular 1,3-dipolar cycloaddition of alkenyl hydrazones obtained from a steroidal D-seco-aldehyde with differently substituted arylhydrazines. The reaction rates were observed to be affected significantly by the electronic character of the substituents on the aromatic moiety. The cyclizations are assumed to follow a stepwise rather than a pure concerted mechanism, to afford arylpyrazolidines as primary products. Spontaneous oxidation of the saturated N-heterocycles under the reaction conditions led to pyrazoline derivatives in good to excellent yields. In in vitro antiproliferative studies on a panel of breast cancer cells (MCF7, T47D, MDA-MB-231, and MDA-MB-361), some of the 3-deacetylated cycloadducts exerted marked growth inhibitory activities, with IC50 values in the range 3.56–9.32 μM, which are comparable to that for the reference agent cisplatin.

Original languageEnglish
Pages (from-to)511-527
Number of pages17
JournalMolecular Diversity
Volume19
Issue number3
DOIs
Publication statusPublished - Aug 2 2015

Keywords

  • Antiproliferative effect
  • Arylpyrazoline
  • Lewis acid
  • Stereoselectivity
  • Steroid
  • [3 + 2] Cycloaddition

ASJC Scopus subject areas

  • Catalysis
  • Information Systems
  • Molecular Biology
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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