Synthetic Studies of Imidazole C-Nucleosides toward Biofunctional Molecules

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  • 生体機能性分子を目的としたイミダゾール C-ヌクレオシドの合成研究
  • セイタイ キノウセイ ブンシ オ モクテキ ト シタ イミダゾール C ヌクレオシド ノ ゴウセイ ケンキュウ

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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 H3 receptor (hH3R) agonist, imifuramine, and the first selective human histamine H4 receptor (hH4R) 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-C2-PA) with a combination of POM and 2-cyanoethyl groups. 5) Incorporation of C2-imidazole nucleoside into position 638 of VS ribozyme using Imz-C2-PA and catalytic activities of the thereby generated modified VS ribozyme (G638C2Imz).<br>

Journal

  • YAKUGAKU ZASSHI

    YAKUGAKU ZASSHI 130 (12), 1707-1724, 2010-12-01

    The Pharmaceutical Society of Japan

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