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Synthesis and Antiviral Activity of Novel 4',5'-Branched Pyrimidine Nucleosides  

Kim Aihong (College of Pharmacy, Chosun University)
Kooh Dae-Ho (HAWON Pharm. Coporation)
Ko Ok Hyun (College of Pharmacy, Chosun University)
Hong Joon Hee (College of Pharmacy, Chosun University)
Publication Information
YAKHAK HOEJI / v.49, no.1, 2005 , pp. 20-24 More about this Journal
Abstract
The synthesis of 4',5'-doubly branched carbocyclic nucleosides was accomplished in this study. The selective methylation in the 5'-position was made by Felkin-Anh controlled Grignard addition. The construction of the required 4'-quaternary carbon was carried out by using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural pyrimidine bases (cytosine, uracil, thymine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited weak antiviral activity against the HCMV.
Keywords
doubly branched nucleoside; antiviral agents; grignard addition; felkin-anh model;
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