Syntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential

Simple item page
dc.contributor.authorHalay E.
dc.contributor.authorAy E.
dc.contributor.authorŞalva E.
dc.contributor.authorAy K.
dc.contributor.authorKarayıldırım T.
dc.date.accessioned2024-07-22T08:10:35Z
dc.date.available2024-07-22T08:10:35Z
dc.date.issued2017
dc.description.abstractWith 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.
dc.identifier.DOI-ID10.1080/15257770.2017.1346258
dc.identifier.issn15257770
dc.identifier.urihttp://akademikarsiv.cbu.edu.tr:4000/handle/123456789/15290
dc.language.isoEnglish
dc.publisherTaylor and Francis Inc.
dc.subjectAntineoplastic Agents
dc.subjectCell Line, Tumor
dc.subjectChemistry Techniques, Synthetic
dc.subjectHumans
dc.subjectPurine Nucleosides
dc.subjectPyrans
dc.subjectPyrimidine Nucleosides
dc.subjectTriazoles
dc.subject1 [[1' (1 deoxy 2",3":4",5" di o isopropylidene beta dextro fructopyranos 1" yl) 1' h 1',2',3' triazole 4' yl)methyl]thymine
dc.subject1 [[1' (1"' deoxy 2",3":4",5" di o isopropylidene beta dextro fructopyranos 1" yl) 1' h 1',2',3' triazol 4' yl]methyl]uracil
dc.subject1 [[1' (2",3",4" tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine
dc.subject1 [[1' (2",3",4"' tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil
dc.subject1 [[1' (2",3",4",6" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil
dc.subject1 [[1' (2",3",4",6"' tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine
dc.subject1 [[1' (6" deoxy 1",2":3"',4" di o isopropylidene alpha dextro galactopyranos 6" yl) 1' h 1',2',3' triazol 4' yl]methyl]thymine
dc.subject1 [[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 fluorouracil
dc.subject1 [[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 fluorouracil
dc.subject1 [[1'(6" deoxy 1",2":3",4" di o isopropylidene alpha dextro galactopyranos 6" yl) 1' h 1',2',3' triazol 4' yl]uracil]
dc.subject9 [[1' (1" deoxy 2",3":,4",5" di o isopropylidene alpha dextro fructopyranos 1"' yl) 1' h 1',2',3' triazole 4' yl]methyl]adenine
dc.subject9 [[1' (2",3",4" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine
dc.subject9 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine
dc.subject9 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine
dc.subject9 [[1' (6" deoxy 1",2":3",4" di o isopropylidene alpha dextro galactopyranos 6"' yl) 1' h 1',2',3' triazole 4' yl]methyl]adenine
dc.subjectantineoplastic agent
dc.subjectcarbohydrate derivative
dc.subjectpurine
dc.subjectpyrimidine
dc.subjecttriazole derivative
dc.subjectunclassified drug
dc.subjectantineoplastic agent
dc.subjectpurine nucleoside
dc.subjectpyran derivative
dc.subjectpyrimidine nucleoside
dc.subjecttriazole derivative
dc.subjectantineoplastic activity
dc.subjectArticle
dc.subjectcancer cell line
dc.subjectcell viability
dc.subjectcontrolled study
dc.subjectdrug cytotoxicity
dc.subjectdrug screening
dc.subjectdrug synthesis
dc.subjectelectrospray mass spectrometry
dc.subjectHep 3B2.1-7 cell line
dc.subjectheteronuclear multiple bond correlation
dc.subjectheteronuclear single quantum coherence
dc.subjecthuman
dc.subjecthuman cell
dc.subjectin vitro study
dc.subjectinfrared spectroscopy
dc.subjectMTT assay
dc.subjectnuclear magnetic resonance
dc.subjecttime of flight mass spectrometry
dc.subjecttwo-dimensional imaging
dc.subjectchemistry
dc.subjectsynthesis
dc.subjecttumor cell line
dc.titleSyntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential
dc.typeArticle

Files

Collections

Scopus Koleksiyonu