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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 31, Number 9
BKCSDE 31(9)
September 20, 2010 

Synthesis of SATE Prodrug of 6'-Fluoro-6'-methyl-5'-noradenosine Nucleoside Phosphonic Acid as a New Class of Anti-HIV Agent
Hua Li, Jin Cheol Yoo, Young Chan Baik, Wonjae Lee, Joon Hee Hong*
Anti-HIV agent, SATE prodrug, Nucleoside phosphonic acid, Mitsunobu reaction
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 N6-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.
2514 - 2518
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