A series of 3-benzylamino-and 3-arylalkylaminocarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazoles 1—12 were synthesized and biologically assayed as geometrically constrained analogues of N-benzylindolylglyoxylylamides II, which are high affinity ligands at the benzodiazepine receptor (BzR). The intermediate 3-ethoxycarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazol-4(10H)-one 14 and its N(10)-methyl analogue 15 closely related to 3-alkoxycarbonyl-β-carbolines I were also investigated. The title compounds exhibited a lower affinity compared with the corresponding indolylglyoxylylamide derivatives II. Attempts were made to rationalize these results taking into account the possible tautomeric equilibria involving these ligands.
Geometrically Constrained Analogues N-Benzylindolylglyoxylylamides: [1,2,4]Triazino[4,3-a]benzimidazol-4(10H)-one Derivatives as Potential New Ligands at the Benzodiazepine Receptor.
DA SETTIMO PASSETTI, FEDERICO;TALIANI, SABRINA;MARINI, ANNA MARIA;SIMORINI, FRANCESCA;TRINCAVELLI, MARIA LETIZIA;MARTINI, CLAUDIA
2003-01-01
Abstract
A series of 3-benzylamino-and 3-arylalkylaminocarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazoles 1—12 were synthesized and biologically assayed as geometrically constrained analogues of N-benzylindolylglyoxylylamides II, which are high affinity ligands at the benzodiazepine receptor (BzR). The intermediate 3-ethoxycarbonyl [1, 2, 4]triazino [4, 3-a]benzimidazol-4(10H)-one 14 and its N(10)-methyl analogue 15 closely related to 3-alkoxycarbonyl-β-carbolines I were also investigated. The title compounds exhibited a lower affinity compared with the corresponding indolylglyoxylylamide derivatives II. Attempts were made to rationalize these results taking into account the possible tautomeric equilibria involving these ligands.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
