Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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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)
  • Received : 2010.09.27
  • Accepted : 2010.11.22
  • Published : 2011.02.20
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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.

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References

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