Stereoselective Synthesis of 4鈥?Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents

详细信息    查看全文

• 作者：Pramod K. Sahu ; Gyudong Kim ; Jinha Yu ; Ji Yoon Ahn ; Jayoung Song ; Yoojin Choi ; Xing Jin ; Jin-Hee Kim ; Sang Kook Lee ; Sunghyouk Park ; Lak Shin Jeong
• 刊名：Organic Letters
• 出版年：2014
• 出版时间：November 7, 2014
• 年：2014
• 卷：16
• 期：21
• 页码：5796-5799
• 全文大小：369K
• ISSN：1523-7052

文摘

Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5鈥?OH for phosphorylation, 4鈥?selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5鈥?Homo-4鈥?selenonucleosides (n = 2) demonstrated potent antiherpes simplex virus (HSV-1) activity, indicating that the bulky selenium atom might play a key role in preventing phosphorylation by cellular kinases, resulting in no antiviral activity.