Purines. LXVI. Adenine 7-Oxide : Its Synthesis, Chemical Properties, and X-ray Molecular Structure

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概要

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• 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.

• 社団法人日本薬学会の論文
• 1995-01-15

著者

• 岡村 公生

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

• 伊達 忠正

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

• 斎藤 徹

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  金沢大学薬学部

• 小林 恵子

  Faculty Of Pharmaceutical Sciences Toyama Medical And Pharmaceutical University

• 小川 和男

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 板谷 泰助

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Kobayashi K

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 板谷 泰助

  金沢大学薬学部

• 岡村 公生

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• Saito T

  Research And Development Headquarters Hokurikit Seiyaku Co. Ltd.

• 伊達 忠正

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• Ogawa K

  Showa Pharmaceutical University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

• 小林 恵子

  Faculty Of Pharmaceutical Sciences Kanazawa University

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