Benzodiazepine Receptor Binding Activity of 8-Substituted-9-(3-substituted-benzyl)-6-(dimethylamino)9H-purines

Article abstract of DOI:10.1021/jm00163a032

A series of 8-substituted analogues of 9-(3-aminobenzyl)-6-(dimethylamino)-9H-purine (8) were synthesized and tested for their ability to bind to the benzodiazepine receptor (BZR) in rat brain tissue.The most active compound was the 8-bromo-9-(3-formamidobenzyl) analogue 16 (IC₅₀ = 0.011 μM), which was 1000-fold more active than the parent 9-benzyl-6-(dimethylamino)-9H-purine (1) and nearly as active as diazepam.Although substitution of a m-formamido group and an 8-bromo substituent on 1 imparted potent BZR binding activity, neither 16 nor 17 analogues exhibited significant anxiolytic activity on a modified Geller-Seifter conflict schedule.