Nucleosides: XI. Synthesis and Antiviral Evaluation of 5'-Alkylthio-5'-deoxy Quinazolinone Nucleoside Derivatives as S-Adenosyl-L-homocysteine Analogs

TC Chien, CS Chen, FH Yu, JW Chern

Index: Chien, Tun-Cheng; Chen, Chien-Shu; Yu, Fang-Hwa; Chern, Ji-Wang Chemical and Pharmaceutical Bulletin, 2004 , vol. 52, # 12 p. 1422 - 1426

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Citation Number: 58

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- ...