8-Aza-7-deaza-2',3'-dideoxyadenosine: Synthesis and conversion into allopurinol 2',3'-dideoxyribofuranoside.

DOI Web Site
  • SEELA FRANK
    Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück
  • KAISER KLAUS
    Laboratorium für Organische und Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück

書誌事項

公開日
1988
DOI
  • 10.1248/cpb.36.4153
公開者
公益社団法人 日本薬学会

この論文をさがす

説明

4-Amino-1-(2, 3-dideoxy-β-D-glycero-pentofuranosyl)-1H-pyrazolo [3, 4-d] pyrimidine (5) was synthesized from 8-aza-7-deaza-2'-deoxyadenosine (1). Benzoylation of the 4-amino group of 1 followed by 4, 4'-dimethoxytritylation of the 5'-hydroxyl function gave 2b. Barton deoxygenation of the phenoxythiocarbonyl compound 3 afforded 4a and yielded 5 after removal of the protecting groups. The N-glycosylic bond stability of 5 to acid was higher than that of 2', 3'-dideoxyadenosine (ddA). Compound 5 showed no appreciable activity against human immunodeficiency virus. It was converted into allopurinol 2', 3'-dideoxyribofuranoside (6) by adenosine deaminase but at a lower rate than the conversion of ddA into ddl.

収録刊行物

キーワード

詳細情報 詳細情報について

問題の指摘

ページトップへ