Nucleosides (6) Synthesis and Antiviral Evaluation of 5'-Alkylthio-5'-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs

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  • Chien Tun-Cheng
    School of Pharmacy, College of Medicine, National Taiwan University No. 1, Section 1
  • Chen Chien-Shu
    School of Pharmacy, College of Medicine, National Taiwan University No. 1, Section 1
  • Yu Fang-Hwa
    School of Pharmacy, College of Medicine, National Taiwan University No. 1, Section 1
  • Chern Ji-Wang
    School of Pharmacy, College of Medicine, National Taiwan University No. 1, Section 1

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タイトル別名
  • Nucleosides: XI. Synthesis and Antiviral Evaluation of 5'-Alkylthio-5'-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs

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説明

4-Amino-1-(β-D-ribofuranosyl)quinazolin-2-one (3) was prepared by a direct glycosylation of 4-aminoquinazolin-2-one (7) using the Vorbruggen's silylation method and provided exclusively the β-anomer. This quinazoline nucleoside and its 2′,3′-O-isopropylidene derivative (9) did not undergo the coupling reaction with dialkyl disulfides in the presence of tri-n-butylphosphine unless their 4-amino groups were protected by N,N-dimethylaminomethylidene. This approach provides a viable alternative synthetic route to 5′-alkylthio-5′-deoxy nucleosides.

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