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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 32, Number 2
BKCSDE 32(2)
February 20, 2011 

Role of Hydroxymethyl Group as a New Hydrophilic 4'-Pocket in 5'-Norcarbocyclic Nucleoside Analogues
Lian Jin Liu, Joon Hee Hong*
Anti-HIV agents, 4'-Hydroxymethyl branched nucleoside, Phosphonic acid nucleosides
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 (EC50 = 8.61 μM) in the CEM cell line.
411 - 416
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