Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent

  • Li, Hua (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Yoo, Jin-Cheol (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Baik, Young-Chan (Hawon Pharmaceuticals Co.) ;
  • Lee, Won-Jae (BK21- Project Team, College of Pharmacy, Chosun University) ;
  • Hong, Joon-Hee (BK21- Project Team, College of Pharmacy, Chosun University)
  • Received : 2010.06.23
  • Accepted : 2010.07.15
  • Published : 2010.09.20
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Abstract

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

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References

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