Synthesis of 5-substituted 7,9-dihydro-8H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-8-ones as anticonvulsant agents

5-(4-Aminobenzyl)-7,9-dihydro-8H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-8-one (3) and 7,9-dihydro-5-[2-(pyridin-2-yl)-vinyl]-8H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-8-one (4) were synthesized and screened as anticonvulsant agents in DBA/2 mice against sound-induced seizures. The new compounds are provided with anticonvulsant properties even if ED50 values are lower than those of prototype 5-(4-aminophenyl)-7,9-dihydro-8H-[1,3]dioxolo[4,5-h][2,3]benzodiazepin-8-one (2) and of GYKI 52466 (1), a well-known noncompetitive AMPA receptor antagonist. Binding assays and functional tests were performed to evaluate the affinity for AMPA and kainate receptors.