• 대한약학회:학술대회논문집
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• 대한약학회 2003년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.238.3-239
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• 2003

Among 4'-substituted nucleosides. Nucleocidin. 4'-azido thymidine (ADRT), 4'-fluorinated carbocyclic nucleoside. and 3'-fluoro oxetanosin analogue have demonstrated a variety of biological activities. Since the cyclopentane ring of carbocyclic nucleosides can emulate the furanose moiety. a number of these compounds exhibit interesting biological activity, particularly in the areas of antiviral and anticancer chemotherapy. (omitted)

• Bulletin of the Korean Chemical Society
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• 제30권11호
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• pp.2626-2630
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• 2009

2'($\beta$)-Hydroxymethylated adenosine is a potent and selective inhibitor of hepatitis C virus (HCV) replication. It targets the RNA-dependent RNA polymerase of HCV, NS5B. Synthesis and antiviral evaluation of carbocyclic versions are described. The cyclopentene intermediate ($9\beta$) was successfully synthesized through sequential Johnson-Claisen orthoester rearrangement and ring-closing metathesis (RCM). Coupling of bases via a Pd(0) catalyst, selective dihydroxylation, and desilylation yielded the target nucleoside analogues. The compounds 17 and 18 were assayed for their ability to inhibit HCV RNA replication in a subgenomic replicon Huh7 cell line and showed moderate antiviral activity with toxicity up to 20.0 and 24.7 ${\mu}g/mL$, respectively.