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http://dx.doi.org/10.5012/bkcs.2011.32.2.411

Role of Hydroxymethyl Group as a New Hydrophilic 4'-Pocket in 5'-Norcarbocyclic Nucleoside Analogues  

Liu, Lian Jin (BK-21 Project Team, College of Pharmacy, Chosun University)
Hong, Joon-Hee (BK-21 Project Team, College of Pharmacy, Chosun University)
Publication Information
Bulletin of the Korean Chemical Society / v.32, no.2, 2011 , pp. 411-416 More about this Journal
Abstract
Steric and electronic parameters of 4'-substituents play significant roles in steering the conformation of nucleoside analogues. In order to investigate the relationship of 4'-group with antiviral enhancement, novel 4'-hydroxymethyl-5'-norcarbocyclic adenosine phosphonic acid analogues were designed and synthesized from 2,2-dimethyl-1,3-dioxolane-4-ethanol (5) using reiterative Grignard addition and ring-closing metathesis (RCM) as key reactions. The synthesized adenosine phosphonic acids analogues (22) and (23) were subjected to antiviral screening against HIV-1. Compound (23) exhibited moderate anti-HIV activity ($EC_50$ = 8.61 ${\mu}M$) in the CEM cell line.
Keywords
Anti-HIV agents; 4'-Hydroxymethyl branched nucleoside; Phosphonic acid nucleosides;
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