Synthetic Nucleosides and Nucleotides. XIX. Synthesis of 3'-Deoxycytidine 5'-Triphosphate and Related 3'-Deoxy-ribonucleotides from Cordycepin'

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概要

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• The pyrimidine 3'-deoxyriboside 5'-triphosphates, pyrimidine counterparts of cordycepin 5'-triphosphate, (1) were conveniently synthesized from cordycepin as potential deoxyribonucleic acid (DNA)-dependent ribonucleic acid (RNA) polymerase inhibitors. For the synthesis of 3'-deoxycytidine, p-chlororobenzoylation of 1 followed by acetolysis afforded an anomeric mixture of 1-O-acetyl-2,5-di-O-p-chlorobenzoyl-3-deoxy-D-ribofuranose (3) in good yield. Condensation of 2,4-bis-trimethylsilyl-N_4-acylcytosine (4a, b) with 3 in the presence of stannic chloride gave fully acylated 3'-deoxycytidine (5) in excellent yield. The protecting group was removed to give 3'-deoxycytidine (6), which on phosphorylation gave 3'-deoxycytidine 5'-monophosphate (7), a key intermediate in the present study. Deamination of 7 with nitrous acid afforded 3'-deoxycytidine-5'-monophosphate (8). Additionally, 2,4-bis-trimethylsilyloxy-5-methyl-or ethylpyrimidine (4c, d) was coupled with 3 in a similar manner to give fully acylated 5-methyl-(5c) or 5-ethyl-3'-deoxyuridine (5d). The 5'-monophosphates were converted to the corresponding 5'-triphosphates by the phosphoroimidazolidate method.

• 公益社団法人日本薬学会の論文
• 1982-06-25

著者

• 中山 智加男

  Division Of Medicinal Chemistry Faculty Of Pharmaceutical Sciences Hokkaido University

• 実吉 峯郎

  Faculty Of Pharmaceutical Sciences Hokkaido University

• 実吉 峯郎

  Division of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hokkaido University

• 遠山 純一

  Division of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, Hokkaido University

• 遠山 純一

  Division Of Medicinal Chemistry 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. 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
• Synthetic Nucleosides and Nucleotides. XI. : Facile Synthesis and Antitumor Activities of Various 5-Fluoropyrimidine Nucleosides
• 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
• IHN ウイルス化学療法へのアプローチ

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