Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants

A comparison of enaminones from various unsubstituted and p-substituted ben zamides to the analogous benzylamines has been undertaken with the aim of e lucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocycloh ex-3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimet hyl-3-N-(benzylamino)-cyclohex-2-en-1-one, 3r indicated that benzylamines p ossessed significant anti-maximal electroshock seizure (MES) activity. Eval uation of the analogous benzamides revealed significant differences in anti convulsant activity, these differences were most probably related to the di fferences in their three-dimensional structures. (C) 1999 Elsevier Science Ltd. All rights reserved.