New approach to 5-arylamino-4-(5-aryloxyfuran-2-yl)pyrimidines: synthesis and antibacterial activity

A method for the synthesis of previously unknown 5-arylamino-substituted 4-(5-aryloxy-furan-2-yl)pyrimidines containing methyl and methoxy groups at different positions of the aryl substituents was developed. The method is based on the combination of the Buchwald-Hartwig cross-coupling reaction with various anilines and nucleophilic substitution of the nitro group by phenolate anions. All the new compounds were screened against 15 different pathogenic bacterial strains. 4-[5-(3,4,5-Trimethoxyphenoxy)furan-2-yl]-substituted pyrimidines were found to possess high antibacterial activity against gonococcal infections, in some cases ten times higher than that of the commercial drug Spectinomycin.