5-O-Alkylated derivatives of 5-hydroxy-2'-deoxyuridine as potential antiviral agents. Anti-herpes activity of 5-propynyloxy-2'-deoxyuridine.

Abstract

Alkylation of 5-hydroxyuridine or 5-hydroxy-2'-deoxyuridine with various activated alkylating agents in the presence of 1 equiv of NaOH gave a series of new nucleoside analogues which were evaluated for antiviral activity against vaccinia virus, herpes simplex-1 virus, and vesicular stomatitis virus in both primary rabbit kidney cells and human skin fibroblasts. One of these analogues, 5-propynyloxy-2'-deoxyuridine, was a potent inhibitor of herpes simplex virus. Structure-activity considerations suggest that the anti-herpes activity is dependent on the integrity of the acetylene group since substitution of phenyl, p-nitrophenyl, vinyl, carboxamido, or carboxyl for the triple bond led to diminished antiviral activity.

• Authors: P F Torrence, J W Spencer, A M Bobst
• Journal: Journal of medicinal chemistry (J Med Chem) Vol. 21 Issue 2 Pg. 228-31 (Feb 1978) ISSN: 0022-2623 [Print] United States
• PMID: 202709 (Publication Type: Journal Article)

Chemical References

• Antiviral Agents
• propynyloxy-2'-deoxyuridine
• Deoxyuridine

Topics

• Antiviral Agents (chemical synthesis)
• Cytopathogenic Effect, Viral (drug effects)
• Deoxyuridine (analogs & derivatives, chemical synthesis, pharmacology)
• Simplexvirus (drug effects)
• Structure-Activity Relationship
• Vaccinia virus (drug effects)
• Vesicular stomatitis Indiana virus (drug effects)