Journal
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
Volume 53, Issue 6, Pages 1547-1555Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/jccs.200600202
Keywords
alpha-2,3-sialyltransferase; 5 '-triazole nucleosides; click chemistry; inhibitory assay; structure-based drug design approach
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The first series of 5'-triazole cytidines 1a-d and adenosines 2a-c was prepared and evaluated for inhibitory potency toward alpha-2,3-sialyltransferase. The synthesis of target compounds was achieved by converting the 5'-alcohol of protected nucleosides to the azide derivatives, which were then coupled with the alkynes by copper(I)-catalyzed cycloaddition to give protected 5'-triazole nucleosides 3a-d/7a-c, followed by deprotection. 5'-Triazole adenosines 2a-c were less efficient inhibitors of alpha-2,3-sialyltransferase than their cytidine analogues 1a-d. 1d was the most active compound with an IC50 of 37.5 mu M. These results suggested that the hydrophobic functionality and the cytidine group are clearly required for the improved binding.
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