| Abstract: | A series of 6-substituted-9-(3-formamidobenzyl)purines were synthesized and studied for benzodiazepine receptor (BZR) binding activity. Most of the target compounds were prepared by reaction of 6-chloro-9-(3-formamidobenzyl)-9H-purine ( 17 ) with the appropriate amine, alcohol or other nucleophilic reagent. Alternatively, the 6-cyclopropylaminopurine 5 was synthesized via the nitrobenzyl precursor 22 , and the 6-alkyl-thiopurines 14 and 15 were prepared by alkylation of the appropriate purine with 3-formamidobenzyl bromide. Purines with a variety of 6-substituents retained potent BZR binding properties, although certain bulky 6-substituents led to compounds with diminished activity. None of the compounds exhibited significant activity on a modified Geller-Seifter Conflict schedule. |
