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

Article abstract of DOI:10.1021/jm00137a010

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