THE DESIGN, SYNTHESIS AND ANTILEUKEMIC ACTIVITY OF 5-ALKYNYL-1-β-D-RIBOFURANOSYLIMIDAZOLE-4-CARBOXAMIDES

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概要

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• The design, synthesis and antileukemic activity of 5-alkynel-1-β-D-ribofuranosylimidazole-4-carboxamides (6) are described. The cross-coupling reaction of 5-iodo-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide (8) with various terminal alkynes in the persence of bis(benzonitrile)palladium dichloride and triethylamine in acetonitrile gave 5-alkylnyl derivatives (9) in high yields. Coupling of 8 with (trimethylsilyl)acetylene gave hte undesired dimer (10). Instead of (trimethylsilyl)acetylene, treatment of trimethyl[(tributyl-satannyl)ethynyl]silane with 8 in the absence of triethylamine produced the desired 5-[2-(trimethylsilyl)ethynyl] derivative (9f) in 77% yield. Deblocking of these nucleosides (9) gave the target nucleosides (6a-f). Among them, 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxyamide (6f) is the most potent inhibitor of the growth of murine L1210 cells in vitro (IC_<50>=0.18 μg/ml).

• 1988-07-25

著者

• 佐々木 琢磨

  Cancer Research Institute Kanazawa University

• 上田 亨

  Faculty of Pharmaceutical Science, Hokkaido University

• 松田 彰

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 上田 亨

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 松田 彰

  北海道大学大学院薬学研究院

• 佐々木 琢磨

  金沢大 がん研

• 南川 典昭

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 上田 亨

  北海道大学薬学部

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