New anticonvulsants: Schiff bases of γ-aminobutyric acid and γ-aminobutyramide

Article abstract of DOI:10.1021/jm00180a029

Schiff bases of γ-aminobutyric acid (γAbu) and γ-aminobutyramide (γAbuNH₂) were prepared and tested for anticonvulsant and γAbu mimetic activity. 4-[[(4-Chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanoic acid monosodium salt (4) and 4-[[(4-chlorophenyl)(5-fluoro-2-hydroxyphenyl)methylene]amino]butanamide (5) blocked bicuculline-induced lethality and convulsions and displaced [³H]γAbu from its membrane binding sites. In the rat dorsal root sensory ganglion, compound 4 exhibited γAbu agonist properties. Compounds 4 and 5 are thus anticonvulsants and directly acting γAbu mimetics.