1) Quinaldic acid hydrazide was reacted with various aldehydes to form the corresponding hydrazones (I to XIII), (XVI) was reacted with 2-nitrofurfural,
p-dimethylaminobenzaldehyde,
p-hydroxybenzaldehyde, and
p-acetamidobenzaldehyde to form the corresponding hydrazones (XVII to XX), and (I) and (VII) were led to their acetylated compounds (XIV and XV) by treatment with acetic anhydride.
2) Oxidation of quinaldic acid with hydroxide in acetic acid solution or hydrolysis of quinaldonitrile 1-oxide with sodium hydroxide in ethanol afforded (XXI). Hydrolysis of (XXIII) with ethanolic sodium hydroxide results in deoxygenation to form cinchoninc acid. Therefore, (XXIII) was converted to (XXV) by the Radziszewsky's method, then to (XXVI) with sulfuric acid and sodium nitrite, and (XXI) and (XXVI) were esterified with diazomethane to be converted to (XXVII) and (XXVIII). Reaction of these with hydrazine hydrate afforded the hydrazides (XXIX and XXX). Condensation of (XXX) with
p-dimethylaminobenzaldehyde and
p-hydroxybenzaldehyde, and that of (XXX) with
p-dimethylaminobenzaldehyde afforded the corresponding hydrazones (XXXI to XXXIII) Examinations were made of the antibacterial power of these compounds against the most potent human-type tubercle bacilli, Frankfurt strain.
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