A one-pot method for the synthesis of structural type urease inhibitors, 2-amino-1,3,4-oxadiazoles, was developed. The structures of the compounds were established using spectroanalytical techniques and unambiguously confirmed by single-crystal X-ray analysis of compound 3o. The synthesized compounds were tested against jack beans urease, and most of the compounds (3c, 3g, 3j, 3k, 3n, 3r-3v) were found more active than the standard. The most potent compound (3u) had an IC50 value of 6.03 ± 0.02 μm as compared to the IC50 value of the standard (thiourea; 22.0 ± 1.2 μm). The prominent urease inhibition activity of these compounds may serve as an important finding in the development of less toxic and more potent antiulcer drugs. The compounds were also investigated against four bacterial strains, and some of the compounds (3g and 3r) were found more potent than the standard drug (ciprofloxacin) against all the tested strains. The MIC value for compound 3g was 0.156 μmol/mL against the tested bacterial strains.
Keywords: acid hydrazides; antibacterial; crystal structure; one-pot synthesis; oxadiazoles; phenoxy acids; urease inhibition.
© 2014 John Wiley & Sons A/S.