Synthesis of 4'-C-ethynyl-beta-D-arabino- and 4'-C-ethynyl-2'-deoxy-beta- D-ribo-pentofuranosyl pyrimidines, and their biological evaluation.
4'-C-Ethynyl-beta-D-arabino-pentofuranosyl thymine (14) and cytosine (16), and 4'-C-ethynyl-2'-deoxy-beta-D-ribo-pentofuranosyl thymine (25) and cytosine (27) were synthesized by properly protected 4'-C-hydroxy-methyl-3,5-di-O-benzyl-alpha-D-ribo-pentofuranose (1) from D-glucose. Among them, 2'-deoxy derivatives 25 and 27 exhibited antiviral activity, while cytidine derivatives 16 and 27 inhibited the growth of neoplastic cells.
Kohgo
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Department of Applied Biological Chemistry, Faculty of Agriculture, Tohoku University, Sendai, Japan.
Horie
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Ohrui
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D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D007942:Leukemia, Experimental / Q000188:drug therapy; D019384:Nucleic Acid Synthesis Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D018139:Simplexvirus / Q000187:drug effects; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D019384:Nucleic Acid Synthesis Inhibitors; D009705:Nucleosides; D011743:Pyrimidines