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In order to find new and potent drug candidates for the treatment of  Helicobacter pylori infections‚ in this study attention was focused on the  synthesis and anti-H. pylori activity of a series of 5-(5-nitrofuran-2-  yl)-1,3,4-thiadiazoles containing piperazinyl functionality at the C-2  position of the 1,3,4-thiadiazole ring. The synthesis of 1-[5-(5-nitrofuran-  2-yl)-1,3,4-thiadiazol-2-yl]piperazine derivatives (3a-h) and pyrrolidine  derivative 3i was achieved with a versatile and efficient synthetic route  via 2-chloro-5-(5-nitrofuran-2-yl)-1,3,4-thiadiazole. The inhibitory  activity of the new derivatives 3a-i against twenty clinical H. pylori  strains was evaluated by the disc diffusion method and compared with the  commercially available standard drug metronidazole Resulting biological data  indicated that most compounds exhibited strong inhibitory activity even at  doses lower than 2 μg disc-1 (average of inhibition zone >20 mm) while  metronidazole had little or no growth inhibition at this dose. Compound 3c  containing the N-benzoylpiperazin-1-yl moiety showed the most potent  inhibitory activity.

journal of the serbian chemical society

Synthesis and biological activity of 5-nitrofuran-containing (1,3,4-thiadiazol-2-yl)piperazine moieties as a new type of anti-Helicobacter pylori heterocycles