Design and Synthesis of Novel Carbocyclic Versions of 2´-spirocyclopropyl Ribonucleosides as Potent Anti-HCV Agents
- Design and Synthesis of Novel Carbocyclic Versions of 2´-spirocyclopropyl Ribonucleosides as Potent Anti-HCV Agents
- 오창현; 김은애; 홍준희
- anti-HCV agent; spirocarbocyclic nucleoside; spirocyclopropylation
- Issue Date
- Nucleosides, nucleotides & nucleic acids
- VOL 30, NO 6, 423-439
- 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).
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