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
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実吉 峯郎
Faculty of Pharmaceutical Sciences, Hokkaido University
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実吉 峯郎
Faculty Of Pharmaceutical Sciences Hokkaido University
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渡部 伸一
Faculty Of Pharmaceutical Sciences Hokkaido University
関連論文
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