6¡ä-Methyl-5¡ä-homoaristeromycin: A structural variation of the anti-orthopox virus candidate 5¡ä-homoaristeromycin

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• 作者：Minmin Yang ; Wei Ye ; Stewart W. Schneller ; ^{schnest@auburn.edu}
• 关键词：Carbocyclic nucleosides ; TADDOL-organozinc stereoselective reaction ; Antiviral activity
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2013
• 出版时间：15 July, 2013
• 年：2013
• 卷：21
• 期：14
• 页码：4374-4377
• 全文大小：526 K

文摘

The synthesis of 6¡ä-methyl-5¡ä-homoaristeromycin is described from a known 6¡ä-ethyl ester. Antiviral analysis showed the (S)-6¡ä stereoisomer retained the vaccinia activity of the parent 5¡ä-homoaristeromycin (1) while the (R)-6¡ä isomer was less active. Both were weaker than 1 towards cowpox. The diastereomers were equally active versus Epstein Barr virus while (S)-6¡ä was three times more active toward vesicular stomatitis virus than (R)-6¡ä. The diastereomers were inactive towards numerous other viruses. The CC₅₀ for both diastereomers was >300 ¦ÌM.