Platelet Aggregation Inhibitors. IX. Chemical Transformation of Adenosine into 2-Thioadenosine Derivatives
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概要
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A facile synthesis of 2-thioadenosine (IX) and its derivatives from adenosine (I) was described. Treatment of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-benzyloxime (IV), obtained via 3 steps from I, with CS_2-MeOH-pyridine at room temperature gave N^1-benzyloxy-2-thioadenosine (VII) which was readily transformed into 2-benzylthioadenosine N-oxide (VIII) by heating. Treatment of IV with CS_2-MeOH-NaOH at 180°in an autoclave gave a mixture of 2-thioadenosine (IX), 2-methylthioadenosine (X) and 2-benzylthioadenosine (XI). Reaction of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamidoxime (XV) obtained from I with CS_2-MeOH-H_2O at 120°in an autoclave gave IX in an overall yield of 60% (practically 2 steps). Treatment of XV with CS_2-MeOH-pyridine at room temperature yielded 2-thioadenosine N-oxide (XVIII) which was subsequently transformed into IX by H_2S. Adenines (XX) were also transformed into 2-thioadenine or 9-benzyl-2-thioadenine (XXV) by treatment of the intermediate compounds (XXII) of carboxamidoxime-type with CS_2-MeOH-H_2O at 120°.
- 公益社団法人日本薬学会の論文
- 1977-08-25
著者
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菊川 清見
Tokyo College of Pharmacy
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菊川 清見
Research Laboratory, Division of Fermentation and Chemical Products, Kohjin Co., Ltd.
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末広 日出男
Research Laboratories, Kohjin Company, Ltd.
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青木 旦治
Research Laboratories, Kohjin Company, Ltd.
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末広 日出男
Research Laboratories Kohjin Company Ltd.
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青木 旦治
Research Laboratories Kohjin Company Ltd.
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