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http://dx.doi.org/10.5012/bkcs.2010.31.9.2514

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)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.9, 2010 , pp. 2514-2518 More about this Journal
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.
Keywords
Anti-HIV agent; SATE prodrug; Nucleoside phosphonic acid; Mitsunobu reaction;
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