title: Synthesis and Biological Evaluation of 9-Deazaadenine 5'-Deoxy-6',6'-Difluoro-Carbocyclic C-Nucleoside Phosphonic Acid Derivatives.
abstract: The first synthetic route to 5'-deoxy-6',6'-difluoro-carbocyclic C-nucleoside [9-deazaadenosine, (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available epichlorohydrin 5 was described. The key C-C bond formation from cyclopentanone to base precursor was performed using the Knoevenagel-type condensation. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV and anti-leukemic activities. They showed moderate cytotoxicity-derived anti-HIV and anti-leukemic activities.
authors.affiliation: a BK21-Project Team, College of Pharmacy, Chosun University , Kwangju , South Korea.
authors.forename: Seyeon
authors.initials: S
authors.lastname: Kim
authors.affiliation: a BK21-Project Team, College of Pharmacy, Chosun University , Kwangju , South Korea.
authors.forename: Joon Hee
authors.initials: JH
authors.lastname: Hong
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives*; D000818:Animals; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D045744:Cell Line, Tumor; D015195:Drug Design; D015497:HIV-1 / Q000187:drug effects; D006801:Humans; D007938:Leukemia / Q000188:drug therapy*; D051379:Mice; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000494:pharmacology; D011684:Purine Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D019380:Anti-HIV Agents; D000970:Antineoplastic Agents; D010757:Phosphorous Acids; D011684:Purine Nucleosides; D000225:Adenine
keywords: Antiviral agent; C-nucleoside; Knoevenagel reaction; anti-leukemic agent