Synthesis of 2'-fluoro and 2',4'-dimethyl pyrimidine C-nucleoside analogues as potential anti-HCV agents.
Stereoselective synthesis of novel 2'-fluoro and 2',4'-dimethyl carbocyclic pyrimidine C-nucleoside analogues using selective fluorination of an epoxide opening reaction is described. The key fluorinated intermediate 7 was prepared from the epoxide intermediate 5 via selective ring opening of the epoxide. Synthesis of isonucleosidic bases through the mesylate 7 and final deprotection provided the target carbocyclic pyrimidine C-nucleoside analogues. The synthesized compounds 15 and 18 were evaluated as inhibitors of the hepatitis C virus (HCV) in the Huh-7 cell line in vitro.
Liu
Lian Jin
LJ
BK21- Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Hong
Joon Hee
JH
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D045744:Cell Line, Tumor; D016174:Hepacivirus / Q000187:drug effects*; D006801:Humans; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism
D000998:Antiviral Agents; D011741:Pyrimidine Nucleosides