Benzodiazepine receptor ligands. 4. Synthesis and pharmacological evaluation of 3-heteroaryl-8-chloropyrazolo[5,1-c][1,2,4] benzotriazine 5-oxides.
The synthesis of new 3-heteroaryl-8-chloropyrazolo[5,1-c][1,2, 4]benzotriazine 5-oxides and their binding activities at the central benzodiazepine receptor (BZR) are reported. The derivatives substituted at the 3-position with electron-rich five-membered rings, such as pyrrole 11, 2-thiophene 13c, or 3-thiophene 13d, showed good affinity values for BZR. In in vivo tests the 3-(thien-3-yl)-8-chloropyrazolo[5,1-c][1,2,4] benzotriazine 5-oxide (13d) showed selective anticonvulsant activity.
Costanzo
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Dipartimento di Scienze Farmaceutiche, Università degli Studi di Firenze, Via Gino Capponi 9, 50121 Firenze, Italy. Costanzo@farmfi.scifarm.unifi.it
Guerrini
G
G
Ciciani
G
G
Bruni
F
F
Selleri
S
S
Costa
B
B
Martini
C
C
Lucacchini
A
A
Aiello
P M
PM
Ipponi
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A
D000818:Animals; D014151:Anti-Anxiety Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D000927:Anticonvulsants / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D002417:Cattle; D002540:Cerebral Cortex / Q000378:metabolism; D003497:Cyclic N-Oxides / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D066298:In Vitro Techniques; D008024:Ligands; D008297:Male; D051379:Mice; D009125:Muscle Relaxants, Central / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology; D011869:Radioligand Assay; D011963:Receptors, GABA-A / Q000378:metabolism*; D014227:Triazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism / Q000494:pharmacology
C119802:3-(thien-3-yl)-8-chloropyrazolo(5,1-c)(1,2,4)benzotriazine 5-oxide; D014151:Anti-Anxiety Agents; D000927:Anticonvulsants; D003497:Cyclic N-Oxides; D008024:Ligands; D009125:Muscle Relaxants, Central; D011963:Receptors, GABA-A; D014227:Triazines