title: Synthesis, characterization and anticonvulsant activity of enaminones. Part 6: Synthesis of substituted vinylic benzamides as potential anticonvulsants.
abstract: A comparison of enaminones from various unsubstituted and p-substituted benzamides to the analogous benzylamines has been undertaken with the aim of elucidating the essential structural parameters necessary for anticonvulsant activity. Initial studies on methyl 4-N-(benzylamino)-6-methyl-2-oxocyclohex-3-en-1-oate, 3a, 3-N-(benzylamino)cyclohex-2-en-1-one, 3p, and 5,5-dimethyl-3-N-(benzylamino)-cyclohex-2-en-1-one, 3r indicated that benzylamines possessed significant anti-maximal electroshock seizure (MES) activity. Evaluation of the analogous benzamides revealed significant differences in anticonvulsant activity, these differences were most probably related to the differences in their three-dimensional structures.
authors.affiliation: Department of Chemistry, Graduate School of Arts and Sciences, Howard University, Washington, DC 20059, USA.
authors.forename: J E
authors.initials: JE
authors.lastname: Foster
authors.forename: J M
authors.initials: JM
authors.lastname: Nicholson
authors.forename: R
authors.initials: R
authors.lastname: Butcher
authors.forename: J P
authors.initials: JP
authors.lastname: Stables
authors.forename: I O
authors.initials: IO
authors.lastname: Edafiogho
authors.forename: A M
authors.initials: AM
authors.lastname: Goodwin
authors.forename: M C
authors.initials: MC
authors.lastname: Henson
authors.forename: C A
authors.initials: CA
authors.lastname: Smith
authors.forename: K R
authors.initials: KR
authors.lastname: Scott
mesh_terms: D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D001549:Benzamides / Q000737:chemistry* / Q000494:pharmacology; D001596:Benzylamines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D018360:Crystallography, X-Ray; D004558:Electric Stimulation; D008297:Male; D051379:Mice; D008958:Models, Molecular; D051381:Rats; D017207:Rats, Sprague-Dawley; D012640:Seizures / Q000188:drug therapy; D013329:Structure-Activity Relationship
chemical_list: D000927:Anticonvulsants; D001549:Benzamides; D001596:Benzylamines