Purines. LI. Synthesis and Biological Activity of Hypoxanthine 7-N-Oxide and Related Compounds
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概要
- 論文の詳細を見る
A detailed account is given of the first chemical synthesis of hypoxanthine 7-N-oxide (5), which started from coupling of 6-chloro-5-nitro-4(3H)-pyrimidinone (7) with N-(4-methoxybenzyl)phenacylamine, generated in situ from the hydrochloride (8), and proceeded through cyclization of the resulting phenacylaminopyrimidinone (9) and removal of the 4-methoxybenzyl group. The results of catalytic hydrogenolysis, methylation followed by catalytic hydrogenolysis, and rearrangement under acidic conditions of 5 supported the correctness of the assigned structure. An ultraviolet spectroscopic approach suggested that the neutral species of 5 exists in H_2O mainly as the N(7)-OH tautomer (21). In the in vitro bioassay of antileukemic activity against murine L5178Y cells, 5 was weakly cytotoxic, with IC_<50> of 100μg/ml. It did not show any antimicrobial activity even at 1000μg/ml. None of the 9-(4-methoxybenxyl) (11) and O-methyl (12,13,and 14) derivatives was found to be antiieukemic or antimicrobial.
- 社団法人日本薬学会の論文
- 1992-03-25
著者
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斎藤 徹
Faculty Of Pharmaceutical Sciences Kanazawa University
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藤井 澄三
Faculty Of Pharmaceutical Sciences Kanazawa University
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小川 和男
Research Institute, Taiho Pharmaceutical Co., Ltd.
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小川 和男
Faculty Of Pharmaceutical Sciences Kanazawa University
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板谷 泰助
Faculty of Pharmaceutical Sciences, Kanazawa University
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野原 富士夫
Research Laboratories, Ikeda Mohando Co., Ltd.,
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西井 正廣
Research Laboratories, Ikeda Mohando Co., Ltd.,
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板谷 泰助
金沢大学薬学部
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Saito T
Research And Development Headquarters Hokurikit Seiyaku Co. Ltd.
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Ogawa K
Showa Pharmaceutical University
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Nohara F
Research Laboratories Ikeda Mohando Co. Ltd.
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野原 富士夫
Research Laboratories Ikeda Mohando Co. Ltd.
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西井 正廣
Research Laboratories Ikeda Mohando Co. Ltd.
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藤井 澄三
Shinshu Univ. Nagano Jpn
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西井 正廣
Research Laboratories, Ikeda Mohando Co., Ltd.
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