Previously we have demonstrated that 4-quinolinecarboxylic acid amides and hydrazides, substituted at position 2, exhibit pronounced antiinflammatory and analgesic activity at a quite low toxicity [1 -5]. It was established that the charaeter and strength of the pharmacological action depend on the type of substituents at positions 2 and 4 of the quinoline cycle.As is known, introduction of the aroylpyruvoyl fragment into amides and hydrazides imparts to them a high antiinflammatory and analgesic activity [6,7]. In this connection, we have synthesized cinehoninie acid hydrazides containing aroylpyruvoyl fragments at the 15-nitrogen atom. The new compounds, namely, 13-aroylpyruvoyl hydrazides of 2-methyl-(I) and 2-phenyl-4-quinolinecarboxylic (II) acids were obtained using a reaction of 5-aryl-2,3-dihydro-2,3-furandiones with 2-methyl-and 2-phenyl-4-quinolinecarboxylic acids according to the scheme.Compounds I and II appear as white crystalline substances (except for Ih) poorly soluble in ethanol, benzene, chloroform, and acetonitrile, and soluble in DMSO and DMF. Their structures were established using the data of elemental analyses and the results of IR and IH NMR spectroscopic measurements. Similarly to the other pyruvic acid derivatives, the synthesized compounds provide red coloration of an ethanol solution of iron(Ill) chloride, which is evidence for the presence ofenolic hydroxyl [9,10].The IH NMR spectra of compounds Ia-Ih, IIb, and IIe contain signals attributed to the protons of methyl group (2.28-2.71 ppm), methoxy group (3.65-3.75ppm), and methine group (6.83-7.21 ppm), and a group of signals belonging to the protons of benzene ring and quinoline cycle I For the previous communication of this series see [1].
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