Synthesis and antiviral activity of cyclopropyl-spirocarbocyclic adenosine, (4R,5S,6R,7R)-4-(6-amino-9H-purin-9-yl)-7-(hydroxymethyl)spiro[2.4]heptane-5,6-diol against hepatitis C virus

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• 作者：Srinivas Gadthula^a ; Ravindra K. Rawal^a ; Ashoke Sharon^a ; Dong Wu^a ; Brent Korba^b ; Chung K. Chu^a ; ^{DCHU@rx.uga.edu"" rel=""nofollow}
• 关键词：Carbocyclic nucleoside ; Anti-HCV ; NS5B ; X-ray structure
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2011
• 出版时间：1 July 2011
• 年：2011
• 卷：21
• 期：13
• 页码：3982-3985
• 全文大小：403 K

文摘

An efficient method was developed for the synthesis of 6-exocyclic methylene carbocyclic intermediate 4. The Simmons–Smith cyclopropanation protocol was applied on the 6-exocyclic methylene of intermediate 4 and demonstrated its utility for the synthesis of novel class of a spiro-carbocyclic nucleoside analog 8. The titled compound 8 demonstrated a significant antiviral activity against HCV with EC₅₀ values of 0.273 and 0.368 μM in genotypes 1A and 1B, respectively.