1,2,3-TRIAZOLODIAZEPINES .1. PREPARATION AND BENZODIAZEPINE RECEPTOR BINDING OF 1-BENZYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES AND 1-PHENETHYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES

摘要

Several new 1,2,3-triazolo[4,5-b][1,4]diazepines were prepared starting from 1-benzyl-1 and 1-phenethyl-4,5-diamino-1,2,3-triazole 2 (Scheme 1), by condensation reactions with beta-diketones (Scheme 2), beta-ketoesters (Scheme 3), and diethyl malonates (Scheme 4). In the first case we obtained compounds 3 and 4 with basic properties, while the ester function condensations gave cyclic amide derivatives 7, 8, 10, 12 and 13 with acid properties. Some N-methyl derivatives 11, 14 and 15 were obtained from the cyclic amide compounds. Most of compounds were tested for their ability to displace [H-3]flunitrazepam from bovine brain membranes but no compound showed benzodiazepine receptor binding affinity. [References: 13]