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. (C) 2009 Published by Elsevier Ltd.