title: Design and synthesis of carbocyclic versions of furanoid nucleoside phosphonic Acid analogues as potential anti-hiv agents.
abstract: Novel 5'-norcarbocyclic adenine and guanine phosphonic acid analogues with 6',6'-difluorine moiety were designed and synthesized from commercially available epichlorohydrin 5. A regioselective Mitsunobu reaction successfully proceeded from an allylic functional group 16b at low reaction temperature in polar cosolvent to give purine phosphonate analogues 17 and 24, respectively. The purine nucleoside phosphonate and phosphonic acid analogues were subjected to antiviral screening against HIV-1. Adenine analogue 21 and its SATE prodrug 29 show significant anti-HIV activity in MT-4 cell lines.
authors.affiliation: BK-21 Project Team , College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
authors.forename: Eunae
authors.initials: E
authors.lastname: Kim
authors.forename: Guang Huan
authors.initials: GH
authors.lastname: Shen
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives*; D019380:Anti-HIV Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D002460:Cell Line; D015195:Drug Design; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D006147:Guanine / Q000031:analogs & derivatives*; D015497:HIV-1 / Q000187:drug effects*; D006801:Humans; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D005663:Furans; D063065:Organophosphonates; D006147:Guanine; D000225:Adenine