Synthesis and anticonvulsant activity of some tetracyclic indole derivatives

Article abstract of DOI:10.1021/jm00361a010

Several related series of cycloalkyl[4,5]pyrrolo[3,2,1-ij]quinolines 7a-g, 8a-c, 10a-e, and 16a-f and indolo[3,2,1-hi]indoles 22a-c and 23a,b were synthesized and tested for anticonvulsant activity. The key preparative step, a Fischer indole reaction between a bicyclic hydrazine and a cyclic ketone, gave the compounds in 34-96% yield. The products were tested in rat maximal electroshock for anticonvulsant activity. Several compounds showed good activity, with 6-[(dimethylamino)methyl]-4,5,6,8,9,10-hexahydrocyclopenta[4,5]pyrrolo[3,2 ,1-ij]quinoline (7d) and N-methyl-4,5,6,8,9,10,11,12-octahydrocyclohepta[4,5]pyrrolo[3,2,1-ij]quino line-6-carboxamide (10c) having ED₅₀'s of 12.5 and 12.9 mg/kg po, respectively.