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Synthesis and Biological Evaluation of 5′‐Triazole Nucleosides
Author(s) -
Lee Lenselot,
Chang KaiHsuan,
Valiyev Famil,
Liu HsingJang,
Li WenShan
Publication year - 2006
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.200600202
Subject(s) - chemistry , cytidine , triazole , 1,2,3 triazole , cycloaddition , stereochemistry , alcohol , azide , combinatorial chemistry , potency , click chemistry , organic chemistry , catalysis , in vitro , biochemistry , enzyme
The first series of 5′‐triazole cytidines 1a‐d and adenosines 2a‐c was prepared and evaluated for inhibitory potency toward α‐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 α‐2,3‐sialyltransferase than their cytidine analogues 1a‐d . 1d was the most active compound with an IC 50 of 37.5 μM. These results suggested that the hydrophobic functionality and the cytidine group are clearly required for the improved binding.