Anticonvulsant activity of 2- and 3-aminobenzanilides

• Published in: Journal of medicinal chemistry Vol. 29; no. 8; pp. 1534 - 1537
• Main Authors: Clark, C. Randall, Lin, Ching Ming, Sansom, Ricky T
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.08.1986
• Subjects: Anilides - chemical synthesis; Anilides - therapeutic use; Aniline Compounds - chemical synthesis; Aniline Compounds - therapeutic use; Animals; Anticonvulsants - chemical synthesis; Anticonvulsants - therapeutic use; Chemistry; Electroshock; Exact sciences and technology; Male; Mice; Noncondensed benzenic compounds; Organic chemistry; Pentylenetetrazole; Phenobarbital - therapeutic use; Phenytoin - therapeutic use; Preparations and properties; Seizures - chemically induced; Seizures - drug therapy; Vertebrata; Mammalia; Structure activity relation; Mouse; Aminoamide; Animal; Rodentia; Benzenic compound; Anticonvulsant; Biological activity
• ISSN: 0022-2623; 1520-4804
• DOI: 10.1021/jm00158a038

A series of 2- and 3-aminobenzanilides derived from ring-alkylated anilines were prepared and evaluated for anticonvulsant activity. These benzanilides were prepared in the course of studies designed to determine the relationship between the benzamide structure and anticonvulsant effects. The compounds were tested in mice against seizures induced by maximal electroshock (MES) and pentylenetetrazole and in the rotorod assay for neurologic deficit. The 3-aminobenzanilide derived from 2,6-dimethylaniline, 21, was the most potent anti-MES compound, with an ED50 of 13.48 mg/kg and a protective index of 21.11 (PI = TD50/ED50). The activity profile for 21 compares favorably with that for phenobarbital and phenytoin.