Structure-activity relationship in cinnamamides. 3. Synthesis and anticonvulsant activity evaluation of some derivatives of (E)- and (Z)-m-(trifluoromethyl)cinnamamide

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Abstract
The (E)- and (Z)-meta-(trifluoromethyl)-.alpha.,.beta.-dimethylcinnamides and some of their N-alkyl derivatives were prepared and pharmacologically tested, in mice, as anticonvulsant agents to verify if a ring substituent, like the meta-CF3 group, different from a halogen but possessing the same electronic effect could lead to equally active compounds. Some (E)-meta-(trifluoromethyl)-.alpha.-methyl- and non-methyl-substituted-cinnamamdes were prepared and tested. In the .alpha.,.beta.-dimethyl series the results show that the meta-CF3 group leads to products more active than the ones substituted on the phenyl ring but still less active than the p-halogen-substituted compounds previously studied. In the .alpha.-methyl and non-methyl-substituted series, the trend shows the meta-CF3 group being able to produce less toxic and, in some cases, more active products than the previously studied amides.