环丙基螺环碳环腺苷的合成及其抗丙型肝炎病毒活性，（4R,5S,6R,7R）-4-（6-氨基-9H-嘌呤-9-基）-7-（羟甲基）螺[2.4]庚烷-5,6-二醇。
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.
机构信息
Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens, GA 30602, USA.
出版信息
Bioorg Med Chem Lett. 2011 Jul 1;21(13):3982-5. doi: 10.1016/j.bmcl.2011.05.012. Epub 2011 May 11.
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 EC(50) values of 0.273 and 0.368 μM in genotypes 1A and 1B, respectively.
开发了一种高效的方法来合成 6-环外亚甲基碳环中间体 4。Simmons-Smith 环丙烷化反应被应用于中间体 4 的 6-环外亚甲基上，并证明了其在合成新型螺环碳核苷类似物 8 中的应用。标题化合物 8 对 HCV 具有显著的抗病毒活性，在基因型 1A 和 1B 中的 EC(50)值分别为 0.273 和 0.368 μM。
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