2-Benzazepines. 4. [1,2,3]Triazolo[4,5-d][2]benzazepines and dibenzo[c,f][1,2,3]triazolo[3,4-a]azepines: synthesis and evaluation as central nervous system agents

• Published in: Journal of medicinal chemistry Vol. 26; no. 3; pp. 367 - 372
• Main Authors: Trybulski, E J, Benjamin, L, Vitone, S, Walser, A, Fryer, R I
• Format: Journal Article
• Language: English
• Published: United States 01-03-1983
• Subjects: Animals; Behavior, Animal - drug effects; Chemical Phenomena; Chemistry; Diazepam - metabolism; Dibenzazepines - chemical synthesis; Dibenzazepines - pharmacology; Pentylenetetrazole - antagonists & inhibitors; Postural Balance - drug effects; Triazoles - chemical synthesis; Triazoles - pharmacology
• ISSN: 0022-2623
• DOI: 10.1021/jm00357a011

The facile synthesis of [1,2,3]triazolo((4,5-d][2]benzazepines and dibenzo[c,f][1,2,3]triazolo[3,4-a]azepines by the addition of sodium azide to acetylenic benzophenones is described. Examination of the pharmacological data indicates that selected triazolobenzazepines are as potent as diazepam in the anti-pentylenetetrazole test and are weaker in the inclined screen and rotarod tests, suggesting that these compounds have antianxiety properties similar to diazepam with fewer deficits in motor coordination. In addition, a possible diazepam antagonist was found in the triazolo-benzazepine series. The dibenzotriazoloazepines were found to be inactive in four standard CNS screening procedures.