SYNTHESIS OF TRIAZOLYLMETHYL-LINKED NUCLEOSIDE ANALOGS VIA COMBINATION OF AZIDOFURANOSES WITH PROPARGYLATED NUCLEOBASES AND STUDY ON THEIR CYTOTOXICITY

Authors

  • Erkan Halay Scientific Analysis Technological Application and Research Center, Uşak University, 1 Eylul Campus, Uşak 64500
  • Emriye Ay Department of Food Technology, Şebinkarahisar School of Applied Sciences, Giresun University, Yayci Village, Giresun 28800
  • Emine Şalva Department of Pharmaceutical Biotechnology, Faculty of Pharmacy, İnönü University, Elazığ Highway, Malatya 44280
  • Kadir Ay Department of Chemistry, Faculty of Arts and Sciences, Manisa Celal Bayar University, Şehit Prof. Dr. İlhan Varank Campus, Manisa 45030
  • Tamer Karayıldırım Department of Chemistry, Faculty of Science, Ege University, Erzene St., İzmir 35100

DOI:

https://doi.org/10.1007/3948

Keywords:

azido sugars, nucleobases, nucleosides, triazoles, anticancer activity, click chemistry

Abstract

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.

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Published

2018-03-27

Issue

Vol. 54 No. 2 (2018)

Section

Original Papers