Nucleosides XI. Synthesis and antiviral evaluation of 5′-alkylthio- 5′-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs

Tun Cheng Chien, Chien Shu Chen, Fang Hwa Yu, Ji Wang Chern

Research output: Contribution to journalArticle

77 Citations (Scopus)

Abstract

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-dimethyl-aminomethylidene. This approach provides a viable alternative synthetic route to 5′-alkylthio-5′-deoxy nucleosides.

Original languageEnglish
Pages (from-to)1422-1426
Number of pages5
JournalChemical and Pharmaceutical Bulletin
Volume52
Issue number12
DOIs
Publication statusPublished - 2004 Dec 1

Fingerprint

Quinazolinones
Homocysteine
Nucleosides
Antiviral Agents
Quinazolines
Derivatives
Glycosylation
Disulfides
Ac-Nal(1)-Cpa(2)-Pal(3,6)-Arg(5)-Ala(10)-lHRH

Keywords

  • AdoHcy
  • Quinazoline
  • S-adenosyl-L-homocysteine
  • Tri-n-butylphosphine

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

Cite this

Nucleosides XI. Synthesis and antiviral evaluation of 5′-alkylthio- 5′-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs. / Chien, Tun Cheng; Chen, Chien Shu; Yu, Fang Hwa; Chern, Ji Wang.

In: Chemical and Pharmaceutical Bulletin, Vol. 52, No. 12, 01.12.2004, p. 1422-1426.

Research output: Contribution to journalArticle

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