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1,2,3‐Triazolodiazepines. I . Preparation and benzodiazepine receptor binding of 1‐benzyl‐ and 1‐phenethyl‐1,2,3‐triazolo‐[4,5‐ b ][1,4]diazepines
Author(s) -
Biagi Giuliana,
Giorgi Irene,
Livi Oreste,
Scartoni Valerio,
Velo Silvia,
Lucacchini Antonio,
Senatore Generoso,
Barili Pier Luigi
Publication year - 1995
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570320127
Subject(s) - chemistry , amide , flunitrazepam , benzodiazepine , stereochemistry , medicinal chemistry , combinatorial chemistry , receptor , organic chemistry , biochemistry
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 β‐diketones (Scheme 2), β‐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 [ 3 H]flunitrazepam from bovine brain membranes but no compound showed benzodiazepine receptor binding affinity.