Alkylated Pyrimidine Derivatives as Antiviral Agents. I. Syntheses and Antiviral Screening of Alkylpyrimidine and 5-Alkyluracil Nucleoside

• Published in: Chemical & pharmaceutical bulletin Vol. 18; no. 2; pp. 261 - 268
• Main Authors: MURAOKA, MASAKO, TAKADA, ATSUSHI, UEDA, TAKEO
• Format: Journal Article
• Language: English
• Published: Japan The Pharmaceutical Society of Japan 1970
• Subjects: Adenoviridae - drug effects; Alkylation; Antiviral Agents - chemical synthesis; Antiviral Agents - pharmacology; Depression, Chemical; Enterovirus B, Human - drug effects; Nucleosides - chemical synthesis; Nucleosides - pharmacology; Poliovirus - drug effects; Uracil - chemical synthesis; Uracil - pharmacology; Uridine - chemical synthesis; Uridine - pharmacology; Vaccinia virus - drug effects; Viruses - drug effects
• ISSN: 0009-2363; 1347-5223
• DOI: 10.1248/cpb.18.261

In order to find the effective antiviral agents, 5-alkyluracil, 3-alkyluracil, 5-alkylisocytosine, 5-alkyl-6-methylisocytosine, 3-alkyl-6-methyluracil, 5-alkyluracil-1-β-D-glucopyranoside and 5-alkyluracil-1-β-D-ribofuranoside were synthesized and screened as to their antiviral effect on both RNA and DNA containing viruses. For RNA viruses, type-1 Mahoney strain of polio virus and K-2211 strain of ECHO-28 virus were used. For DNA viruses, type-1 and type-12 strains of adeno virus and DV-96 strain of Vaccinia virus were used. Among these tested compounds, 5-butyluracil and 5-butyluracil-1-β-D-ribofuranoside were found to possess effect on both RNA and DNA viruses. Especially, the latter was more effective than the former. Moreover, the latter exerted a broader antiviral spectrum than that of 5-fluorodeoxyuridine.