Studies on specific inhibition of benzodiazepine receptor binding by some C-benzoyl-1,2,3-triazole derivatives

✍ Scribed by G. Biagi; I. Giorgi; O. Livi; A. Lucacchini; C. Martini; V. Scartoni

• Publisher: John Wiley and Sons
• Year: 1993
• Tongue: English
• Weight: 439 KB
• Volume: 82
• Category: Article
• ISSN: 0022-3549
• DOI: 10.1002/jps.2600820906

✦ Synopsis

Certain new (1-15) or previously described (16-25) 1,2,3-triazole derivatives, characterized by a C-benzoyl substituent, were synthesized and tested for their ability to displace [3H]flunitrazepam from bovine brain membrane. Compounds 11a and 9a, bearing neutral and lipophilic substituents (phenethyl and cyclohexyl, respectively) showed the higher activity. The 5-benzoyl isomer 11b presented a lower activity, equivalent to that of the triazole acetic derivative 23, which is 4-benzyl substituted. Generally, the carboxymethyl radical in the 1-position of the triazole ring decreased the activity, probably because of intramolecular hydrogen bonding with the carbonyl function of the benzoyl substituent. The N-1 unsubstituted triazole derivatives 24 and 25 were ineffective; this result is in disagreement with our previous observations. Probably these molecules interact with the receptor site by a hydrogen bonding acceptor group and by a bulky and lipophilic portion or a hydrogen bonding donor function that is appropriately arranged.