Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Racemic Synthesis of Novel 6'-Methylene-5'-norcarbocyclic Purine Phosphonic Acid Analogues via Mitsunobu Reaction

  • Kim, Eun-Ae (BK-21 Project Team, College of Pharmacy, Chosun University) ;
  • 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 : 2011.06.02
  • Accepted : 2011.06.29
  • Published : 2011.08.20
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Abstract

Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6'-electronegative moiety such as unsaturated C-C bond were designed and synthesized from commercially available 2-methylene-propane-1,3-diol (4). Regioselective Mitsunobu reaction successfully proceeded from an allylic functional group (${\pm}$)-12b at low reaction temperature in polar cosolvent (DMF/1,4-dioxane) to give purine phosphonate analogues (${\pm}$)-13 and (${\pm}$)-20. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Guanine analogue (${\pm}$)-23 shows significant anti-HIV activity in PBM cell lines ($EC_{50}=8.1\;{\mu}M$).

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References

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