title: Synthesis and Anti-HIV Activity of Novel 4'-Trifluoromethylated 5'-Deoxycarbocyclic Nucleoside Phosphonic Acids.
abstract: Efficient synthetic route to novel 4'-trifluoromethylated 5'-deoxycarbocyclic nucleoside phosphonic acids was described from α-trifluoromethyl-α,β-unsaturated ester. Coupling of purine nucleosidic bases with cyclopentanol using a Mitsunobu reaction gave the nucleoside intermediates which were further phosphonated and hydrolyzed to reach desired nucleoside analogs. Synthesized nucleoside analogs were tested for anti-HIV activity as well as cytotoxicity. Adenine analog 22 shows significant anti-HIV activity (EC50 = 8.3 μM) up to 100 μM.
authors.affiliation: a BK-21 Project Team, College of Pharmacy, Chosun University , Kwangju , Republic of Korea.
authors.forename: Jun-Pil
authors.initials: JP
authors.lastname: Jee
authors.forename: Seyeon
authors.initials: S
authors.lastname: Kim
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D008826:Microbial Sensitivity Tests; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000494:pharmacology*
chemical_list: D019380:Anti-HIV Agents; D009705:Nucleosides; D010757:Phosphorous Acids
keywords: 4′-trifluoromethylated nucleoside; 5′-deoxycarbocyclic phosphonic acid nucleoside; Antiviral agent