SYNTHESIS AND ANTIVIRAL (RNA) EVALUATION OF NUCLEOSIDE ANALOGS OF TIAZOFURIN MODIFIED AT THE CARBOXAMIDE MOIETY

Abstract The carboxamide functionality of tiazofurin 1a has been modified to produce the following analogs: carboximidates 5a,b, carboxamidines 6, 10, tetrahydropyrimidine 7, N-glycine 8 and N-glutamine 9. These structural modifications abolished the in vitro antiviral (RNA) activity exhibited by tiazofurin against the flaviviruses (yellow fever and Japanese encephalitis viruses), bunyavirus (Punta Toro virus) and togavirus (Venezuelan equine encephalomyelitis virus). Only carboximidates 5a,b retained marginal activity against bunyaviruses.