Syntheses of 1,2,3-triazole-bridged pyranose sugars with purine and pyrimidine nucleobases and evaluation of their anticancer potential
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2017
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Abstract
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. © 2017 Taylor & Francis Group, LLC.
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Antineoplastic Agents , Cell Line, Tumor , Chemistry Techniques, Synthetic , Humans , Purine Nucleosides , Pyrans , Pyrimidine Nucleosides , Triazoles , 1 [[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 , 1 [[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 , 1 [[1' (2",3",4" tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine , 1 [[1' (2",3",4"' tri o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]5 fluorouracil , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil , 1 [[1' (2",3",4",6" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]uracil , 1 [[1' (2",3",4",6"' tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]thymine , 1 [[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 , 1 [[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 , 1 [[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 , 1 [[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]adenine , 9 [[1' (2",3",4" tetra o acetyl beta dextro xylopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine , 9 [[1' (2",3",4",6" tetra o acetyl beta dextro galactopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine , 9 [[1' (2",3",4",6" tetra o acetyl beta dextro glucopyranosyl) 1' h 1',2',3' triazole 4' yl]methyl]adenine , 9 [[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 , antineoplastic agent , carbohydrate derivative , purine , pyrimidine , triazole derivative , unclassified drug , antineoplastic agent , purine nucleoside , pyran derivative , pyrimidine nucleoside , triazole derivative , antineoplastic activity , Article , cancer cell line , cell viability , controlled study , drug cytotoxicity , drug screening , drug synthesis , electrospray mass spectrometry , Hep 3B2.1-7 cell line , heteronuclear multiple bond correlation , heteronuclear single quantum coherence , human , human cell , in vitro study , infrared spectroscopy , MTT assay , nuclear magnetic resonance , time of flight mass spectrometry , two-dimensional imaging , chemistry , synthesis , tumor cell line