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Studies on Specific Inhibition of Benzodiazepine Receptor Binding by Some C-Benzoyl-1,2,3-triazole Derivatives

1993; Elsevier BV; Volume: 82; Issue: 9 Linguagem: Inglês

10.1002/jps.2600820906

1520-6017

G. BIAGI, Irene Giorgi, Oreste Livi, Antonio Lucacchini, Claudia Martini, Valerio Scartoni,

Synthesis of Organic Compounds

Abstract 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 [ 3 H]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.