Synthesis and anticonvulsant activity of analogues of 4-amino-N-(1-phenylethyl)benzamide.
A group of amides and amines related to 4-amino-N-(1-phenylethyl)benzamide, 1, were prepared in a study on the relationship of structure to anticonvulsant activity in this compound. Acylation and alkylation of the amino group of 1 resulted in almost total loss of anticonvulsant activity. Insertion of a methylene between the 4-amino group and the aromatic ring of 1 produced a slight increase in anticonvulsant potency and a significant increase in toxicity. Hydride reduction of the amide carbonyl in 1 also yielded compounds having a slightly lower ED50 against convulsions induced by electroshock and a much lower TD50 in the rotorod assay. Modification of the 1-phenylethyl group of 1 also decreased anticonvulsant potency.
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001549:Benzamides / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051379:Mice; D013329:Structure-Activity Relationship
D000927:Anticonvulsants; D001549:Benzamides