Synthesis of 5-isoxazol-5-yl-2'-deoxyuridines exhibiting antiviral activity against HSV and several RNA viruses.

Abstract

This paper describes a simple method for synthesizing a small library of 5-isoxazol-5-yl-2'-deoxyuridines from 5-iodo-2'-deoxyuridine. Nitrile oxides were generated in situ from oximes using a commercial bleaching agent; their cycloaddition with 5-ethynyl-2'-deoxyuridine yielded isoxazoles possessing activity against herpes simplex viruses 1 and 2, Encephalomyocarditis virus, Coxsackie B3, and vesicular stomatitis virus; these isoxazoles were, however, inactive against corona virus, influenza virus, and HIV.

• Authors: Yoon-Suk Lee, Sun Min Park, Byeang Hyean Kim
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 19 Issue 4 Pg. 1126-8 (Feb 15 2009) ISSN: 1464-3405 [Electronic] England
• PMID: 19147352 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antiviral Agents
• Isoxazoles
• Deoxyuridine

Topics

• Antiviral Agents (chemical synthesis, chemistry, pharmacology)
• Combinatorial Chemistry Techniques
• Deoxyuridine (analogs & derivatives, chemical synthesis, chemistry, pharmacology)
• Isoxazoles (chemical synthesis, chemistry, pharmacology)
• Microbial Sensitivity Tests
• Molecular Structure
• RNA Viruses (drug effects)
• Simplexvirus (drug effects)