title: Efficient electrophilic fluorination for the synthesis of novel 2'-fluoro-3'-methyl-5'-deoxyphosphonic acid apiosyl nucleoside analogues.
abstract: Novel 5'-deoxyapiosyl purine phosphonic acid analogues with a 2'-electropositive moiety, such as, a fluorine atom were designed and synthesized from commercially available hydroxylacetone. Condensation of a glycosyl donor 10 with purines under Vorbruggen conditions and cross-metathesis give the desired nucleoside phosphonic acid analogues 14, 17, 21, and 24. The synthesized nucleoside analogues were subjected to antiviral screening against HIV-1, and the adenine analogue 17 exhibited weak in vitro anti-HIV-1 activity (EC50=26.6 μM).
authors.affiliation: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju , Republic of Korea.
authors.forename: Kyung Mi
authors.initials: KM
authors.lastname: Kim
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D004583:Electrons; D015497:HIV-1 / Q000187:drug effects; D054879:Halogenation; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry* / Q000494:pharmacology; D010429:Pentoses / Q000737:chemistry*; D010757:Phosphorous Acids / Q000737:chemistry*
chemical_list: D000998:Antiviral Agents; D009705:Nucleosides; D010429:Pentoses; D010757:Phosphorous Acids; C570063:phosphonic acid; C004983:apiose