Syntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential
Articles > Article · 2017
Authors: Erkan Halay, Emriye Ay, EMİNE ŞALVA, Kadir Ay, Tamer KARAYILDIRIM
Nucleosides, Nucleotides & Nucleic Acids, Journal Indexed in SCI Expanded, International, WoS, 2017, vol 36, pp 598-619
DOI: 10.1080/15257770.2017.1346258
Summary
With the aim to create a library of compounds with potential bioactivities by combining special characteristics of two important groups such as nucleobases and carbohydrates, twenty 1,4-disubstituted-triazole nucleosides were synthesized in good yields (80-94%) using the copper catalyzed 'Click' reaction between azido-modified pento- or hexopyranoses and alkyne-bearing pyrimidine or purine nucleobases. Structural elucidation was made with the assistance of spectroscopic techniques such as FTIR, 1D-, 2D-NMR, and ESI-TOFMS. All the synthesized triazole nucleosides were evaluated for their cytotoxic activity against three human cancer cell lines (MDA-MB-231, Hep3B, PC-3) by using the MTT assay. Particularly, compounds 3a and 1b were identified as potential hits against Hep3B cell.