Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthetic Studies of Potential Antimetabolites. XII. Synthesis of 4-Substituted 1-(β-D-Ribofuranosyl)-1H-imidazo [4, 5-c] pyridines
水野 義久田沢 節子影浦 邦夫
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1968 年 16 巻 10 号 p. 2011-2017

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4-Hydroxy-1-(β-D-ribofuranosyl)-1H-imidazo [4, 5-c] pyridine (3-deazainosine, XIV) was prepared by use of the corresponding 4-chloro derivative (IX) as a key intermediate. It was found that the reaction of IX with hydrazine afforded either 1-(β-D-ribofuranosyl)-1H-imidazo [4, 5-c] pyridine (XIII) by de-chlorination or 4-hydrazino-1-(β-D-ribofuranosyl)-1H-imidazo [4, 5-c] pyridine (X) depending upon conditions employed. Improved synthesis of IX was achieved by an adaptation of Yamaoka, Matsuda and Aso's method. In addition to X and XIV, a number of other 4-substituted ribonucleosides and nucleotides having imidazo [4, 5-c] pyridine (3-deazapurine) ring system, such as XII, XV, XVI and XVII were prepared.
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