title: Synthesis of novel 2'-spirocyclopropyl-5'- deoxyphosphonic acid furanosyl nucleoside analogues as potent antiviral agents.
abstract: Novel 5'-deoxyfuranosyl purine phosphonic acid analogues with 2 '-electropositive moiety, such as spirocyclopropanoid, were designed and synthesized from commercially available diethyl malonate. Condensation reaction successfully proceeded from a glycosyl donor 15 at low reaction temperature in Vorbruggen conditions to give desired phosphonate analogues 16b and 23b. The synthesized nucleotide analogues 19, 22, 26, and 29 were subjected to antiviral screening against HIV-1. Adenine phosphonic acid analogue 22 shows significant anti-HIV activity (EC(50) = 7.9 μM).
authors: BK21 Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
authors: Guang Huan
authors: GH
authors: Shen
authors: Joon Hee
authors: JH
authors: Hong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D015658:HIV Infections / Q000188:drug therapy; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D010757:Phosphorous Acids / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011687:Purines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013141:Spiro Compounds / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D019380:Anti-HIV Agents; D010757:Phosphorous Acids; D011687:Purines; D013141:Spiro Compounds