title: Synthesis and Anti-HIV Activity of Novel 2'-Deoxy-2'-β-Fluoro-Threosyl Nucleoside Phosphonic Acid Analogues.
abstract: Novel 2'-deoxy-2'-β-fluoro-threose purine phosphonic acid analogues were designed and racemically synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbrüggen conditions. Cross-metathesis of vinyl analogues 13 and 23 with diethyl vinylphosphonate yielded the desired nucleoside phosphonate analogues 14 and 24, respectively. Ammonolysis and hydrolysis of phosphonates yielded the nucleoside phosphonic acid analogues 16, 19, 26, and 29. The synthesized nucleoside analogues were subjected to antiviral screening against human immunodeficiency virus (HIV)-1. Adenine analogue 18 exhibited weak in vitro activities against human immunodeficiency virus (HIV)-1.
authors.affiliation: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju , Republic of Korea.
authors.forename: Seyeon
authors.initials: S
authors.lastname: Kim
authors.affiliation: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju , Republic of Korea.
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D015658:HIV Infections / Q000188:drug therapy* / Q000821:virology; D015497:HIV-1 / Q000187:drug effects / Q000472:pathogenicity; D006801:Humans; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D009705:Nucleosides; D010757:Phosphorous Acids; C570063:phosphonic acid
keywords: 2′-deoxy-2′-fluoro-threose-phosphonic acid analogue; Anti-HIV agents; Vorbrüggen reaction