Refinement of the benzodiazepine receptor site topology by structure-activity relationships of new N-(heteroarylmethyl) indol-3-ylglyoxylamides

…, G Greco, B Cosimelli, M Ehlardo, A Sala…

Index: Primofiore, Giampaolo; Da Settimo, Federico; Marini, Anna Maria; Taliani, Sabrina; La Motta, Concettina; Simorini, Francesca; Novellino, Ettore; Greco, Giovanni; Cosimelli, Barbara; Ehlardo, Marina; Sala, Annalisa; Besnard, Francois; Montali, Marina; Martini, Claudia Journal of Medicinal Chemistry, 2006 , vol. 49, # 8 p. 2489 - 2495

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Citation Number: 22

Abstract

N-(Heteroarylmethyl) indol-3-ylglyoxylamides (1-26) were synthesized and evaluated as ligands of the benzodiazepine receptor (BzR) to probe the hydrogen bonding properties of the so-called S1 site of the BzR by means of suitable heterocyclic side chains. SARs were developed in light of our hypothesis of binding modes A and B. Pyrrole and furan derivatives adopting mode A (2, 8, 10, 20, 22) turned out to be more potent (K i values< 35 nM) than ...