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Synthesis and Antiviral Activity of Novel 2′-Methyl and 4′-Phenyl Branched Carbocyclic Nucleosides  

양선화 (조선대학교 약학대학)
홍준희 (조선대학교 약학대학)
Publication Information
YAKHAK HOEJI / v.48, no.1, 2004 , pp. 88-92 More about this Journal
Abstract
In this study; a series of 2',4'-doubly branched carbocyclic nucleosides (8,9,10) were synthesized from simple acyclic ketone derivative as starting material. The installation of the 4'-quaternary carbon needed was carried out using a 〔3,3〕-sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2'-position was accomplished by Grig-nard reaction. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst. Although all the synthesized compounds were assayed against several viruses, only cytosine analogue 9 showed weak antiviral viral activity (EC$_{50}$=45.4 $\mu$M) against CoxB3 virus.s.
Keywords
branched nucleoside; antiviral agents; grignard reaction; ring-closing metathesis (RCM);
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