Synthesis and anti-Helicobacter pylori activity of (4-nitro-1-imidazolylmethyl)-1,2,4-triazoles, 1,3,4- thiadiazoles, and 1,3,4-oxadiazoles

A series of [(4-nitro-1H-imidazol-1-yl)methyl]-1,2,4-triazoles and 1,3,4-thiadiazoles were prepared and evaluated for their activity against sensitive and resistant H. pylori strains. Study of the structure-activity relationship of these series of compounds indicated that the type of nitroimidazole moiety and the pendent group on the heteroaryl analog dramatically impact the anti-H. pylori activity. In triazole series, compound 5d, containing a 4-methyl phenyl group on the triazole ring, was the most potent compound tested against both metronidazole-sensitive and -resistant strains at a concentration of 8 μg.