T. Smirnova, M. Y. Gavrilov, L. P. Drovosekova
Feb 1, 1998
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Journal
Pharmaceutical Chemistry Journal
Abstract
Isber et al. [1] reported on the synthesis of 5,6,7,8-tetrahydroquinoline-4-carboxylic acid within the framework of the search for new tuberculostatic agents. In the preceding paper [2], we have reported on the synthesis of arylideneand 5-nitrofurfurylidenehydrazides of 2-chloroand 2-arylaminosubstituted 5,6-trimethyleneand 5,6-tetramethyleneisonicotinic acids possessing antimicrobial activity. The purpose of this work was to synthesize substituted hydrazides of 2-chloro-5,6,7,8-tetrahydroquinoline-4-carboxylic acid and characterize them with respect to antibacterial, antiinflammatory, analgesic, and anticonvulsive activity. It was found that 2-chloro-5,6,7,8-tetrahydroquinoline-4carboxylie acid hydrazide (I) readily enters into the condensation reactions with aromatic aldehydes, pyruvic acid or its ethyl ester, and isatin with the formation of substituted hydrazides I I a I l g at a yield o f50-95%. Compounds I I a I Ig appear as yellow or white crystalline substances soluble in DMF and acetic acid (Table 1). The IR absorption spectrum of compound lib shows the bands at 1655 (CO) and 3285 cm-1 (Nit), while the spectrum of compound IIf displays the bands at 1675 and 1710 cmi (two CO groups) and 3180 cm-1 (NH). The IR spectra of the other products also agree with the proposed structures. The structures were confirmed by the IH NMR spectroscopy data as well (Table 2).