Nucleosides XI. Synthesis and antiviral evaluation of 5'-alkylthio-5'-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs.
4-amino-1-(beta-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 beta-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.
Chien
Tun-Cheng
TC
School of Pharmacy, College of Medicine, National Taiwan University No. 1, Section 1, Ren-Ai Road, Taipei, Taiwan.
Chen
Chien-Shu
CS
Yu
Fang-Hwa
FH
Chern
Ji-Wang
JW
D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D006710:Homocysteine / Q000737:chemistry; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D009705:Nucleosides / Q000138:chemical synthesis* / Q000494:pharmacology*; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology*; D012435:S-Adenosylhomocysteine / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000494:pharmacology; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000998:Antiviral Agents; D007202:Indicators and Reagents; D009705:Nucleosides; D011799:Quinazolines; D006710:Homocysteine; D012435:S-Adenosylhomocysteine