Stereoselective Synthesis of 4′-Selenonucleosides via Seleno-Michael Reaction as Potent Antiviral Agents
Organic Letters2014Vol. 16(21), pp. 5796–5799
Citations Over TimeTop 15% of 2014 papers
Prafulla Kumar 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
Abstract
Based on the hypothesis that the bulky selenium atom, with 4p orbitals, can sterically hinder the approach of a cellular kinase to 5'-OH for phosphorylation, 4'-selenonucleosides with one-carbon homologation were designed and synthesized via a novel seleno-Michael reaction, with the stereoselectivity controlled by steric effects. 5'-Homo-4'-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.
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