title: [Synthetic studies of imidazole C-nucleosides toward biofunctional molecules].
abstract: Synthetic studies of C4-linked imidazole C-nucleosides toward biofunctional molecules are described, in which the following items are covered. 1) Stereoselective synthesis of imidazole C- and pyrazole C-nucleosides via diazafulvene intermediates. 2) Synthesis of tetrahydrofuranylimidazoles using a PhSe group efficiently and its application to the new human histamine H(3) receptor (hH(3)R) agonist, imifuramine, and the first selective human histamine H(4) receptor (hH(4)R) agonist, OUP-16. 3) Synthesis of imidazole ribonucleoside phosphoramidite (Imz-PA) with pivaloyloxymethyl (POM) group for probing the catalytic mechanism of ribozymes. 4) Synthesis of a two-carbon-elongated homologue (Imz-C(2)-PA) with a combination of POM and 2-cyanoethyl groups. 5) Incorporation of C(2)-imidazole nucleoside into position 638 of VS ribozyme using Imz-C(2)-PA and catalytic activities of the thereby generated modified VS ribozyme (G638C(2)Imz).
authors.affiliation: Osaka University of Pharmaceutical Sciences, Osaka, Japan.
authors.forename: Lisa
authors.initials: L
authors.lastname: Araki
authors.forename: Shinya
authors.initials: S
authors.lastname: Harusawa
mesh_terms: D006801:Humans; D007093:Imidazoles / Q000138:chemical synthesis*; D008024:Ligands; D009705:Nucleosides / Q000138:chemical synthesis*; D009943:Organophosphorus Compounds; D011720:Pyrazoles; D016337:RNA, Catalytic; D043562:Receptors, G-Protein-Coupled; D011968:Receptors, Histamine; D018100:Receptors, Histamine H3; D000074040:Receptors, Histamine H4; D012263:Ribonucleosides; D013237:Stereoisomerism
chemical_list: C418607:HRH4 protein, human; D007093:Imidazoles; D008024:Ligands; D009705:Nucleosides; D009943:Organophosphorus Compounds; D011720:Pyrazoles; D016337:RNA, Catalytic; D043562:Receptors, G-Protein-Coupled; D011968:Receptors, Histamine; D018100:Receptors, Histamine H3; D000074040:Receptors, Histamine H4; D012263:Ribonucleosides; C113487:diazafulvene; C434331:phosphoramidite; C031280:pyrazole