Efficient synthesis of novel A-ring-substituted 1,2,3- triazolylcholestanederivatives via catalytic azide-alkyne cycloaddition

Zalán Kádár, E. Frank, G. Schneider, Judit Molnár, I. Zupkó, János Kóti, Bruno Schönecker, J. Wölfling

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

A simple and convenient synthetic route is reported for the formation of novel 2α-triazolylcholestane derivatives. The scheme involves transformation of the starting cholestanone to the corresponding azido compound and efficient conversions of 2α-azido-5α-cholestan-3-one (3) with various terminal alkynes through use of the 'click' chemistry approach. Finally, the oxo group of these heterocyclic steroidal derivatives was reduced, and the resultant mixtures of epimeric triazolyl alcohols were separated. The antiproliferative activities of the synthesized 2-triazolyl-3-ketones against three human cancer cell lines were screened. Nevertheless, only a few of the tested compounds exerted moderate cell-growth inhibition.

Original languageEnglish
Pages (from-to)279-296
Number of pages18
JournalArkivoc
Volume2012
Issue number3
DOIs
Publication statusPublished - Jan 29 2012

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Alkynes
Azides
Cycloaddition
Cholestanones
Derivatives
Cell growth
Ketones
Cells
Alcohols

Keywords

  • Cholestanone
  • Click chemistry
  • Cycloaddition
  • Steroid azides
  • Triazoles

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Efficient synthesis of novel A-ring-substituted 1,2,3- triazolylcholestanederivatives via catalytic azide-alkyne cycloaddition. / Kádár, Zalán; Frank, E.; Schneider, G.; Molnár, Judit; Zupkó, I.; Kóti, János; Schönecker, Bruno; Wölfling, J.

In: Arkivoc, Vol. 2012, No. 3, 29.01.2012, p. 279-296.

Research output: Contribution to journalArticle

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AU - Schneider, G.

AU - Molnár, Judit

AU - Zupkó, I.

AU - Kóti, János

AU - Schönecker, Bruno

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AB - A simple and convenient synthetic route is reported for the formation of novel 2α-triazolylcholestane derivatives. The scheme involves transformation of the starting cholestanone to the corresponding azido compound and efficient conversions of 2α-azido-5α-cholestan-3-one (3) with various terminal alkynes through use of the 'click' chemistry approach. Finally, the oxo group of these heterocyclic steroidal derivatives was reduced, and the resultant mixtures of epimeric triazolyl alcohols were separated. The antiproliferative activities of the synthesized 2-triazolyl-3-ketones against three human cancer cell lines were screened. Nevertheless, only a few of the tested compounds exerted moderate cell-growth inhibition.

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