Chemistry of Heterocyclic Compounds

, Volume 54, Issue 2, pp 158–166 | Cite as

Synthesis of triazolylmethyl-linked nucleoside analogs via combination of azidofuranoses with propargylated nucleobases and study on their cytotoxicity

  • Erkan Halay
  • Emriye Ay
  • Emine Şalva
  • Kadir Ay
  • Tamer Karayıldırım
Article
  • 46 Downloads

Copper(I)-catalyzed azide–alkyne 1,3-dipolar cycloaddition reactions (CuAAC) between azidofuranoses and propargyl-nucleobases were carried out in the presence of CuSO4·5H2O and sodium ascorbate as catalytic system to provide the corresponding 1,4-disubstituted-1,2,3-triazole-bridged nucleoside analogs in good yields. Twelve new sugar-based triazolylmethyl-linked nucleoside analogs were synthesized and screened for their cytotoxic activity against MDA-MB-231, Hep3B, PC-3, SH-SY5Y, and HCT-116 cancer cell lines and control cell line (L929). Most of the compounds were moderately effective against all the cancer cell lines assayed. Particularly, among the tested compounds, 1,2,3-triazole-linked 5-fluorouracil–mannofuranose hybrid was found to be the most potent cytotoxic agent against HCT-116, Hep3B, SH-SY5Y cells with IC50 values of 35.6, 71.1, and 75.6 μM, respectively. None of the triazolylmethyl-linked nucleoside analogs exhibited cytotoxic effect against the control cells L929.

Keywords

azido sugars nucleobases nucleosides triazoles anticancer activity click chemistry 

Notes

This work was supported by TUBITAK-Research Council of Turkey with the project number 114Z757. Author E. Halay also offers his profound thanks to TUBITAK-BIDEB 2211A for their bursary support.

Supplementary material

10593_2018_2248_MOESM1_ESM.pdf (3 mb)
ESM 1 (PDF 3057 kb)

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Erkan Halay
    • 1
  • Emriye Ay
    • 2
  • Emine Şalva
    • 3
  • Kadir Ay
    • 4
  • Tamer Karayıldırım
    • 5
  1. 1.Scientific Analysis Technological Application and Research CenterUşak UniversityUşakTurkey
  2. 2.Department of Food Technology, Şebinkarahisar School of Applied SciencesGiresun UniversityGiresunTurkey
  3. 3.Department of Pharmaceutical Biotechnology, Faculty of Pharmacyİnönü UniversityMalatyaTurkey
  4. 4.Department of Chemistry, Faculty of Arts and SciencesManisa Celal Bayar UniversityManisaTurkey
  5. 5.Department of Chemistry, Faculty of ScienceEge UniversityİzmirTurkey

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