Synthesis of disubstituted 1,4-diazepines with affinity to GABAA-receptor subtypes.

A series of tetrahydro-1H-1,4-diazepines 4a-c, dihydro-1H-1,4-diazepine 5 and pyrido diazepines 8 and 10 was prepared. Originated form dehydroacetic acid (DHA) and aromatic aldehydes cinnamoyl compounds 3a-c were obtained and converted with ethylenediamine to give tetrahydro-1H-1,4-diazepines 4a-c. For the synthesis of pyrido[1,2-d][1,4]diazepines 8 and 10 a new snythetic approach is described. Compounds 4b and 5 were investigated concerning their affinity to different benzodiazepine receptor subtypes. The determined IC 50 values for 5 are 1.5 μM and 1.1 μM at 10 μM respectively.