1,2,3-Triazolo[1,5-a][1,4]- and 1,2,3-triazolo[1,5-a]-[1,5]benzodiazepine derivatives: synthesis and benzodiazepine receptor binding.
This paper reports the synthesis of new 1,2,3-triazolo[1,4]benzodiazepine and 1,2,3-triazolo[1,5]benzodiazepine derivatives and their evaluation toward benzodiazepine receptors. Receptor affinity gradually and remarkably increases by moving the nitrogen atom of the central ring from position 3 through 4 to position 5, to give the most effective compound 6a (Ki = 150 nM). N-methylation of the diazepine ring (7a) lowers receptorial binding. Introduction of a chlorine atom on the benzene ring doubles the Ki value (6b) which remains unaltered by the N-methylation (7b).
Bertelli
L
L
Dipartimento di Scienze Farmaceutiche, Facoltà di Farmacia, Università di Pisa, Italy.
Biagi
G
G
Giorgi
I
I
Livi
O
O
Manera
C
C
Scartoni
V
V
Martini
C
C
Giannaccini
G
G
Trincavelli
L
L
Barili
P L
PL
D000818:Animals; D001569:Benzodiazepines / Q000138:chemical synthesis* / Q000378:metabolism; D002417:Cattle; D011963:Receptors, GABA-A / Q000378:metabolism*; D014230:Triazoles / Q000138:chemical synthesis* / Q000378:metabolism
D011963:Receptors, GABA-A; D014230:Triazoles; D001569:Benzodiazepines