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Geometrically Constrained Analogues of N‐Benzylindolylglyoxylylamides: [1, 2, 4]Triazino[4, 3‐ a ]benzimidazol‐4(10 H )‐one Derivatives as Potential New Ligands at the Benzodiazepine Receptor
Author(s) -
Primofiore Giampaolo,
Da Settimo Federico,
Taliani Sabrina,
Marini Anna Maria,
Simorini Francesca,
Novellino Ettore,
Greco Giovanni,
Trincavelli Letizia,
Martini Claudia
Publication year - 2003
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.200300788
Subject(s) - chemistry , tautomer , stereochemistry , benzodiazepine , receptor , biochemistry
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(10 H )‐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.