Imidazole derivatives with potential biological activity

A series of 1-substituted imidazole-5-carbohydroxamic acids Ia, Ib and Ic were prepared from the corresponding 5-methoxycarbonyl imidazoles (IX) obtained by a univocal synthesis starting with the reaction of the amines (III) with ethylchloroacetate. On treatment of 4(5)-methoxycarbonyl imidazoles (XI) with alkylaryl halides (X), on the contrary, mixtures of 1-substituted-4(or 5)-methoxycarbonyl imidazoles were obtained that, when separated by thin-layer chromatography, gave the carbohydroxamic acids Ia, Ib, Id and Ie and IIa leads to f. The structure of the imidazole derivatives were obtained by means of IR, NMR and UV spectra. On carrying out tests of biological activity on these compounds, it had been found that the 5-carbohydroxamic acids possess, compared to the 4-carbohydroxamic ones, a greater activity. Particularly Ib and Ib--HCl seem fairly active against Klebsiella pneumoniae and Clostridium bifermentans, Ib--HCl against Bacillus subtilis, too.