Abstract
In order to examine whether the antibacterial mechanism of 2-γ-pyridyl-1, 3, 4-oxadiazol-5-one (I), prepared by Smith and reported to possess a strong antitubercular activity, is due to isonicotinic acid hydrazide (INAH) formed from it or to the 1, 3, 4-oxadiazol-5-one ring, 2-γ-pyridyl-4-phenyl-(II) and 2-(N-oxy-γ-pyridyl)-1, 3, 4-oxadiazol-5-one (III) were prepared. (II), (III), and m- and p-dimethylamino, nitro, amino, and hydroxy derivatives of 2-phenyl-1, 3, 4-oxadiazol-5-one (IV) were submitted to antibacterial tests but except for (I), the antibacterial activity of these compounds were very weak. This proves that the antibacterial factor is not the oxadiazolone ring but INAH.These compounds tested were prepared by the reaction of phosgene with carboxylic acid hydrazides. Application of phosgene to m- and p-nitrobenzoic acid hydrazides and reduction of the cyclized product afforded the amino compound, whose diazotization followed by decomposition gave the hydroxyl compound. These amino and hydroxyl compounds were also obtained directly by the application of phosgene to the corresponding amino- and hydroxy-benzoic acid hydrazides.
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