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http://dx.doi.org/10.5012/bkcs.2011.32.5.1662

Synthesis and Some Properties of 4'-Phenyl-5'-Norcarbocyclic Adenosine Phosphonic Acid Analogues  

Liu, Lian Jin (BK-21 Project Team, College of Pharmacy, Chosun University)
Kim, Eun-Ae (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.5, 2011 , pp. 1662-1668 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'-substituent with antiviral enhancement, novel 4'-phenyl-5'-norcarbocyclic adenosine phosphonic acid analogues were racemically synthesized via de novo acyclic stereoselective route from propionaldehyde 5. The phenyl substituted cyclopentenols 15a and 15b as key intermediates were successfully constructed via reiterative carbonyl addition of Grignard reagents and ring-closing metathesis of corresponding divinyl 14. The synthesized nucleoside phosphonic acids analogues 19, 20, 21, and 23 were subjected to antiviral screening against HIV-1.
Keywords
Anti-HIV agent; 4'-Branched nucleoside; 5'-Norcarbocyclic nucleoside phosphonic acid;
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