Purines. LXV. Preparatory study for the syntheses of the marine sponge purines agelasimines-A and -B: Synthesis and acetylation of their N(7)-benzyl analogues

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概要

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• Four-step synthetic routes from 3-methyladenine (10) to 7-benzyl-N6,3-dimethyladenine (1b) and 7-benzyl-1,2-dihydro-1,3-dimethyladenine (2b), selected as models for the marine sponge alkaloids agelasimine-A (1a) and agelasimine-B (2a), respectively, have been established. The key steps involved are regioselective methylations of 7-benzyl-3-methyladenine (8) and 7-benzyl-1,2-dihydro-3-methyladenine (11). The reaction of 1b with acetic anhydride in pyridine was found to give the monocyclic imidazole derivative 29b. A similar acetylation of 2b yielded the N6-acetyl derivative 20b. When treated with boiling H2O, 20b afforded 7-benzyl-2,3-dimethylhypoxanthine (21b) and a compound inferred to be the dihydrohypoxanthine derivative 30. Probable pathways to 29b from 1b and to 21b and 30 from 20b are proposed.

• 公益社団法人日本薬学会の論文
• 1994-12-15

著者

• 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

• 大場 正志

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 大場 正志

  Kanazawa Univ. Ishikawa Jpn

• 近澤 淳

  金沢大薬

• 近澤 淳

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 中村 祐子

  Faculty of Pharmaceutical Sciences, Kanazawa University

• Ohba M

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 中村 祐子

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 藤井 澄三

  Shinshu Univ. Nagano Jpn

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