Nucleosides and Nucleotides. 186. Synthesis and Biological Activities of Pyrimidine Carbocyclic Nucleosides with a Hydroxyamino Group Instead of a Hydroxymethyl Group at the 4'-Position of the Sugar Moiety

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概要

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• Pyrimidine carbocyclic nucleosides with a hydroxyamino group instead of a hydroxymethyl group at the 4'-position of the sugar moiety were designed as potential antitumor and/or antiviral agents. Pd(O)-catalyzed reactions of enantiomerically pure (+)-(1R, 4S)-4-[(tert-butyldiphenylsilyl)oxy]-1-(ethoxycarbonyloxy)-2-cyclopentene (9) with N3-benzoylthymine and -uracil gave carbocyclic nucleosides 10 and 11. Subsequent Pd (O)-catalyzed reactions of N3-benzoyl-1-[(1R, 4S)-4-(ethoxycarbonyloxy)-2-cyclopenten-1-yl]thymne (14) and -uracil (15) with O-benzylhydroxylamine smoothly gave the hydroxyamino-substituted carbocyclic nuclesides 16 and 17. From these nucleosides, the target compounds were prepared after deprotection or further reactions. The 2', 3'-didehydro-2', 3'-dideoxythymidine (D4T) analogue 20 was the most effective compound, with IC_<50> values of 27.3 and 34.5μM against KB and L1210 cells in vitor. Carbocyclic analogues of uridine and cytidine (29 and 32) were less effective than 20 against both cell lines.

• 社団法人日本薬学会の論文
• 1999-07-15

著者

• 田中 正一

  Graduate School Of Pharmaceutical Sciences Kyushu University

• Shuto Satoshi

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Tanaka M

  Faculty Of Pharmaceutical Sciences Tokushima Bunri University

• Matsuda A

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Matsuda A

  Faculty Of Pharmaceutical Sciences Hokkaido University

• Matsuda Akira

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• OGAWA Akira

  Graduate School of Pharmaceutical Sciences, Hokkaido University

• TANAKA Motohiro

  Cancer Research Institute, Kanazawa University

• SASAKI Takuma

  Cancer Research Institute, Kanazawa University

• MORI Shuji

  Department of Bacteriology, Fukushima Medical College

• SHIGETA Shiro

  Department of Bacteriology, Fukushima Medical College

• Miura S

  Yamasa Corp. Chiba Jpn

• Matsuda Akira

  Department Of Pharmaceutical Sciences Faculty Of Pharmaceutical Sciences

• Matsuda A

  Hokkaido Univ. Sapporo

• Matsuda Akira

  The Department Of Internal Medicine Kin-ikyo Chuo Hospital

• Sasaki Takuma

  Cancer Research Institute Kanazawa University

• Sasaki Takuma

  Department Of Experimental Therapeutics Cancer Research Insitute Kanazawa University

• Shigeta S

  Fukushima Medical University

• Shigeta Shiro

  Department Of Bacteriology Fukushima Medical College

• Tanaka Motohiro

  Cancer Research Institute Kanazawa University

• Matsuda Akira

  Graduate School Of Pharmaceutical Sciences Hokkaido University

• Mori Shuji

  Department Of Bacteriology Fukushima Medical College

• Ogawa Akira

  Graduate School Of Pharmaceutical Sciences Hokkaido University

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