Purines. LXVI.^<1)> Adenine 7-Oxide: Its Synthesis, Chemical Properties, and X-ray Molecular Structure

• 藤井 澄三

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 小川 和男

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 斎藤 徹

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 小林 恵子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 板谷 泰助

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 伊達 忠正

  Organic Chemistry Research Laboratory, Tanabe Seiyaku, Co., Ltd.

• 岡村 公生

  Organic Chemistry Research Laboratory, Tanabe Seiyaku, Co., Ltd.

抄録

A detailed account is given of the first unequivocal synthesis of adenine 7-oxide (8). The synthesis started with peroxycarboxylic acid oxidation of 3-benzyladenine (6), readily obtainable from adenine (1) by benzylation, and proceeded through nonreductive debenzylation of the resulting 3-benzyladenine 7-oxide (7). The location of the oxygen function in 7 and 8 was confirmed by their chemical reactions including deamination and methylation and by X-ray crystallographic analysis. A UV spectroscopic approach suggested that the neutral species of 8 exists in H_2O as an equilibrated mixture of the N(7)-oxide (8) and N(7)-OH (21) tautomers. Treatment of 6 with 30% aqueous H_2O_2 in MeOH in the presence of MeCN and KHCO_3 at 30℃ produced the N(7)-oxide 7 and 7-acetamido-3-benzyladenine (15) in 12% and 1% yields, respectively.

収録刊行物

• Chemical & pharmaceutical bulletin

  Chemical & pharmaceutical bulletin 43 (1), 53-62, 1995-01-15

  公益社団法人日本薬学会

キーワード

• adenine 7-oxide
• synthesis
• X-ray analysis
• 3-benzyladenine N-oxidation
• debenzylation nonreductive
• reaction adenine 7-oxide

詳細情報

• CRID: 1571417127325378176
• NII論文ID: 110003631289
• NII書誌ID: AA00602100
• ISSN: 00092363
• 本文言語コード: en
• データソース種別:
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