ABSTRACT

3-Acetyl-2-methyl-indole (1) was synthesized by acetylation of 2-methyl indole with acetyl chloride. Facile condensation of compound (1) with various aromatic aldehydes yielded 1-(2’ -methylindolyl) arylidenyl chalcones (2-7), which on treating with 2-aminothiophenol and 2-aminophenol afforded 2-substitutedphenyl-2,3-dihydro-4-(2’ -methylindolyl)-1,5-benzthiazepines (8-13) and 2-substitutedphenyl-2,3-dihydro-4-(2’ -methylindolyl)-1,5-benzoxazepines (14-19), respectively. The structures of all the compounds were delineated by elemental analysis, IR and proton magnetic resonance. The newly synthesized compounds were evaluated for their anticonvulsant activity and were compared with standard drug phenytoin sodium. These compounds were also tested for acute toxicity. Compound 12 was found to be the most potent compound of the series, exhibiting activity of 90 % more potent than standard drug. Compounds 13 and 18 also showed promising activity of 80 %, equipotent to standard drug.