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
2011
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.
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