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http://dx.doi.org/10.5012/bkcs.2012.33.12.4007

Synthesis and Conformation of Novel 4'-Fluorinated 5'-Deoxythreosyl Phosphonic Acid Nucleosides as Antiviral Agents  

Kang, Lien (BK-21 Project Team, College of Pharmacy, Chosun University)
Kim, Eunae (BK-21 Project Team, College of Pharmacy, Chosun University)
Choi, Eun Joo (BK-21 Project Team, College of Pharmacy, Chosun University)
Yoo, Jin Cheol (BK-21 Project Team, College of Pharmacy, Chosun University)
Lee, Wonjae (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.33, no.12, 2012 , pp. 4007-4014 More about this Journal
Abstract
Efficient synthetic route to novel 4'-fluorinated 5'-deoxythreosyl phosphonic acid nucleosides was described from glyceraldehyde using Horner-Emmons reaction in the presence of triethyl ${\alpha}$-fluorophosphonoacetate. Glycosylation reaction of nucleosidic bases with glycosly donor 14 gave the nucleosides which were further phosphonated and hydrolyzed to reach desired nucleoside analogues. Synthesized nucleoside analogues 18, 21, 25 and 28 were tested for anti-HIV activity as well as cytotoxicity. Adenine derivatives 18 and 21 showed significant anti-HIV activity up to $100{\mu}M$.
Keywords
Antiviral agent; 4'-Fluorinated nucleoside; Deoxythreosyl nucleoside; Phosphonic acid nucleoside;
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