Design and Synthesis of Novel Carbocyclic Versions of 2´-spirocyclopropyl Ribonucleosides as Potent Anti-HCV Agents

Title
Design and Synthesis of Novel Carbocyclic Versions of 2´-spirocyclopropyl Ribonucleosides as Potent Anti-HCV Agents
Authors
오창현김은애홍준희
Keywords
anti-HCV agent; spirocarbocyclic nucleoside; spirocyclopropylation
Issue Date
2011-06
Publisher
Nucleosides, nucleotides & nucleic acids
Citation
VOL 30, NO 6, 423-439
Abstract
The discovery of 2´-spirocyclopropyl-ribocytidine as a potent inhibitor of RNA synthesis by NS5B (IC50 = 7.3 μM), the RNA polymerase encoded by hepatitis C virus (HCV), has led to the synthesis and biological evaluation of carbocyclic versions of 2´-spiropropyl-nucleosides from cyclopentenol 6. Spirocyclopropylation of enone 7 was completed by using (2-chloroethyl)-dimethylsulfonium iodide and potassium t-butoxide to form the desired intermediate 9a. The synthesized nucleoside analogues, 18, 19, 26, and 27, were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line. The synthesized cytosine nucleoside 19 showed moderate anti-HCV activity (IC50 = 14.4 μM).
URI
http://pubs.kist.re.kr/handle/201004/40681
ISSN
1525-7770
Appears in Collections:
KIST Publication > Article
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