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http://dx.doi.org/10.5012/bkcs.2013.34.12.3621

Synthesis of Novel 2'-Fluoro-5'-deoxyphosphonic Acids and Bis(SATE) Adenine Analogue as Potent Antiviral Agents  

Shen, Guang Huan (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.34, no.12, 2013 , pp. 3621-3628 More about this Journal
Abstract
Novel 5'-deoxythreosyl purine phosphonic acid analogues containing a 2'-electropositive moiety such as fluorine atom, were designed and synthesized from commercially available 1,3-dihydroxy acetone. Condensation successfully proceeded from a glycosyl donor 6 under Vorbr$\ddot{u}$ggen conditions and cross-metathesis gave the desired phosphonate analogues 7a, 7b, 17a and 17b. The synthesized nucleoside phosphonic acid analogues 13, 16, 23, 26, 28 were subjected to antiviral screening against HIV-1. The bis(SATE) adenine analogue 28 exhibited significant in vitro activities against HIV-1.
Keywords
anti-HIV agents; 2'-Fluoro-5'-deoxyphosphonic acid analogue; Vorbr$\ddot{u}$ggen reaction;
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