Halay E.Ay E.Şalva E.Ay K.Karayıldırım T.2024-07-222024-07-22201715257770http://akademikarsiv.cbu.edu.tr:4000/handle/123456789/15290With 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. © 2017 Taylor & Francis Group, LLC.EnglishAntineoplastic AgentsCell Line, TumorChemistry Techniques, SyntheticHumansPurine NucleosidesPyransPyrimidine NucleosidesTriazoles1 [[1' (1 deoxy 2",3":4",5" di o isopropylidene beta dextro fructopyranos 1" yl) 1' h 1',2',3' triazole 4' yl)methyl]thymine1 [[1' (1"' deoxy 2",3":4",5" di o isopropylidene beta dextro fructopyranos 1" yl) 1' h 1',2',3' triazol 4' yl]methyl]uracil1 [[1' (2",3",4" tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine1 [[1' (2",3",4"' tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil1 [[1' (2",3",4",6" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil1 [[1' (2",3",4",6"' tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine1 [[1' (6" deoxy 1",2":3"',4" di o isopropylidene alpha dextro galactopyranos 6" yl) 1' h 1',2',3' triazol 4' yl]methyl]thymine1 [[1' (6" deoxy 1",2":3",4" di o isopropylidene alpha dextro fructopyranos 1" yl) 1' h 1',2',3' triazole 4' yl)methyl]5 fluorouracil1 [[1' (6" deoxy 1",2":3",4" di o isopropylidene alpha dextro galactopyranos 6" yl) 1' h 1',2',3' triazole 4' yl)methyl]5 fluorouracil1 [[1'(6" deoxy 1",2":3",4" di o isopropylidene alpha dextro galactopyranos 6" yl) 1' h 1',2',3' triazol 4' yl]uracil]9 [[1' (1" deoxy 2",3":,4",5" di o isopropylidene alpha dextro fructopyranos 1"' yl) 1' h 1',2',3' triazole 4' yl]methyl]adenine9 [[1' (2",3",4" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine9 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine9 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine9 [[1' (6" deoxy 1",2":3",4" di o isopropylidene alpha dextro galactopyranos 6"' yl) 1' h 1',2',3' triazole 4' yl]methyl]adenineantineoplastic agentcarbohydrate derivativepurinepyrimidinetriazole derivativeunclassified drugantineoplastic agentpurine nucleosidepyran derivativepyrimidine nucleosidetriazole derivativeantineoplastic activityArticlecancer cell linecell viabilitycontrolled studydrug cytotoxicitydrug screeningdrug synthesiselectrospray mass spectrometryHep 3B2.1-7 cell lineheteronuclear multiple bond correlationheteronuclear single quantum coherencehumanhuman cellin vitro studyinfrared spectroscopyMTT assaynuclear magnetic resonancetime of flight mass spectrometrytwo-dimensional imagingchemistrysynthesistumor cell lineArticle10.1080/15257770.2017.1346258