Structure--activity relationship in cinnamamides. 3. Synthesis and anticonvulsant activity evaluation of some derivatives of (E)- and (Z)-m-(trifluoromethyl)cinnamamide.
The (E)- and (Z)-m-(trifluoromethyl)-alpha, beta-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)-alpha-methyl- and -non-methyl-substituted-cinnamamides were also prepared and tested. In the alpha, beta-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 alpha-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.
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002934:Cinnamates / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051379:Mice; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D000927:Anticonvulsants; D002934:Cinnamates; C030437:3-(trifluoromethyl)cinnamide