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Heterocyclic Communications

Editor-in-Chief: Strekowski, Lucjan

Ed. by Baumstark, Alfons L. / Saczewski, Jaroslaw / Stephens, Chad / Yamada, Hidetoshi

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Volume 19, Issue 2


An approach to C-glycosidic conjugates of isoflavones

Wiesław Szeja / Piotr Świerk / Grzegorz Grynkiewicz / Aleksandra Rusin
  • Maria Sklodowska-Curie Memorial Cancer Center and the Institute of Oncology, Department of Tumor Biology, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Katarzyna Papaj
  • Maria Sklodowska-Curie Memorial Cancer Center and the Institute of Oncology, Department of Tumor Biology, 44-100 Gliwice, Poland
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2013-04-03 | DOI: https://doi.org/10.1515/hc-2013-0023


A novel approach to isoflavone glycoconjugates, designed as less biodegradable congeners of natural glycosides, is presented on example of daidzein linkage to a C-glycosidic synthon derived from l-rhamnose. 1,3-Dipolar cycloaddition was employed for chemical ligation of daidzein 7-O-propargyl ester and alkyl azide containing 2,3-unsaturated pyranoside moiety. The obtained constructs with opposite anomeric configuration both exhibited a considerable increase in cytotoxic activity against the HTC 116 cell line, in comparison to the parent isoflavone.

Keywords: click-chemistry; cytotoxic activity; daidzein; glycoconjugates


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About the article

Corresponding author: Wiesław Szeja, Chemistry Department, Silesian Technical University, 44-100 Gliwice, Poland

Received: 2013-02-06

Accepted: 2013-02-20

Published Online: 2013-04-03

Published in Print: 2013-04-01

Citation Information: Heterocyclic Communications, Volume 19, Issue 2, Pages 133–138, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: https://doi.org/10.1515/hc-2013-0023.

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