Synthetic Nucleosides and Nucleotides. XXVIII. : Synthesis of 5-Alkylcytidines from 5-Alkylbarbituric Acids

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概要

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• 5-Alkylbarbituric acids (1b-f) were converted to 5-alkyl-2,4,6-trichloropyrimidines (2b-f) by using phosphoryl chloride in refluxing n-butyl acetate in the presence of N, N-diethylaniline hydrochloride. Treatment of 2 with sodium methoxide in dry acetonitrile followed by reaction with potassium ethyl mercaptide and desulfurization with Raney Ni afforded 5-alkyl-2,4-dimethoxypyrimidines (5b-f), as key intermediates in the present study. Coupling of 5 with 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of stannic chloride in acetonitrile afforded 5-alkyl-1-(2,3,5-tri-O-benzoyl)-β-D-ribofuranosyl-1,2-dihydro-4-methoxypyrimidin-2-ones (6a-f) in quantitative yields. Ammonolysis of 6 with methanolic ammonia afforded the title 5-alkylcytidines (7a-f). Compounds 6 were also easily converted to their uridine counterparts by treatment with hydrochloric acid. Growth-inhibitory effects of 7 on cultured mouse leukemia L5178Y cells, antiviral activity against a rhabdovirus, infectious hematopoietic necrosis virus (IHNV), in cultured CHSE-214 cells and properties as a substrate of human cytidine deaminase were also examined.

• 公益社団法人日本薬学会の論文
• 1988-07-25

著者

• 実吉 峯郎

  Faculty of Pharmaceutical Sciences, Hokkaido University

• 実吉 峯郎

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 渡部 伸一

  Faculty Of Pharmaceutical Sciences Hokkaido University

関連論文

• Synthetic Nucleosides and Nucleotides. XVI. Synthesis and Biological Evaluations of a Series of 1-β-D-Arabinofuranosylcytosine 5'-Alkyl or Arylphosphates
• Mode of Action of 5-Fluorocytidine and 5-Fluoro-2'-deoxycytidine in L5178Y Cells in Vitro
• Synthetic Nucleosides and Nucleotides. XVI. Synthesis and Biological Evaluations of a Series of 1-β-D-Arabinofuranosylcytosine 5'-Alkyl or Arylphosphates
• Synthetic Nucleosides and Nucleotides. XIII. Stannic Chloride Catalyzed Ribosylation of Several 6-Substituted Purines
• Synthetic Nucleosides and Nucleotides. I. On Synthesis and Properties of Several Thiocyanato Derivatives of Purines and Their Ribonucleosides.
• Biological Photochemistry. I. The Correlation between the Photodynamical Behaviors and the Chemical Structures of Nucleic Acid-bases, Nucleosides, and Related Compounds in the Presence of Methylene-blue
• Resistance of Cyclocytidine to Cytidine Deaminase
• Synthetic Nucleosides and Nucleotides. XVIII. Synthesis and Cytostatic Activity of 5-Fluoropyrimidine Nucleosides of 3-Amino-3-deoxy-β-D-ribofuranose and Related Compounds
• Synthetic Nucleosides and Nucleotides. XIX. Synthesis of 3'-Deoxycytidine 5'-Triphosphate and Related 3'-Deoxy-ribonucleotides from Cordycepin'
• Studies on Hydrogen Exchange. XII. Reaction Mechanism for Hydrogen Exchange of C-8 Hydrogen of Purine Ribosides
• The Correlation between the Antitumor Activities and Chemical Structures of Thiocyanato Derivatives of Purines and Their Ribonucleosides
• Synthetic Nucleosides and Nucleotides. XXVII. Selective Inhibition of Deoxyribonucleic Acid Polymerase α by 1-β-D-Arabinofuranosyl-5-styryluracil 5'-Triphosphates and Related Nucleotides : Influence of Hydrophobic and Steric Factors on the Inhibitory Acti
• 薬学における生物化学と有機化学(薬学第二世紀の出発点に立って)
• Synthetic Nucleosides and Nucleotides. XI. : Facile Synthesis and Antitumor Activities of Various 5-Fluoropyrimidine Nucleosides
• Synthesis and Optical Properties of 2,3-Dideoxy-D-erythro-hex-2-enopyranosyl Nucleosides (Nucleosides and Nucleotides. LXII)
• Synthetic Nucleosides and Nucleotides. XXVIII. : Synthesis of 5-Alkylcytidines from 5-Alkylbarbituric Acids
• Synthetic Nucleosides and Nucleotides. XV. 5-Dimethylamino-2-oxidoisoquinolin-1-yl Diazomethane : A Novel Water-soluble Fluorescent Labelling Agent for Nucleotides
• Synthetic Nucleosides and Nucleotides. IX. Synthesis of 2', 5'- and 3', 5'-Di-O-tritylcytidine and the Related Compounds via Thiation
• Synthetic Nucleosides and Nucleotides. VIII. Direct Synthesis of the 5'-Phosphate of 4-Thiouridine, 6-Thioinosine and 6-Thioguanosine from the Corresponding Oxy Nucleotide via Thiation Procedure
• Synthetic Nucleotides. VII. A Direct Replacement of 6-Thiol Group of 6-Thioinosine with Hydrazine Hydrate
• Synthetic Nucleosides and Nucleotides. VI. On the Several Routes for the Syntheses of 4-Thiouridylic Acid Homologues
• Synthesis and Reaction of 3-Fluoro-4-nitroquinoline 1-Oxide
• Synthetic Nucleosides and Nucleotides. III. On the Syntheses of Several 2,6,8-Trisubstituted Purine Ribonucleosides
• Direct Thiation of Uridine 5'-Phosphate
• Syntheses and Properties of Several 4-Alkyl-or Arylsulfonylquinoline 1-Oxides

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