jm030973k_si_001.pdf (385.96 kB)
N,N-Dialkyl-2-phenylindol-3-ylglyoxylamides. A New Class of Potent and Selective Ligands at the Peripheral Benzodiazepine Receptor
journal contribution
posted on 2004-03-25, 00:00 authored by Giampaolo Primofiore, Federico Da Settimo, Sabrina Taliani, Francesca Simorini, Maria Paola Patrizi, Ettore Novellino, Giovanni Greco, Enrico Abignente, Barbara Costa, Beatrice Chelli, Claudia MartiniWe report the synthesis and the affinity data at both the peripheral (PBR) and the central
benzodiazepine receptors of a series of N,N-dialkyl-2-phenylindol-3-ylglyoxylamide derivatives
III, designed as conformationally constrained analogues of 2-phenylindole-3-acetamides II such
as FGIN-1-27. Most of the new compounds showed a high specificity and affinity for PBR,
with Ki in the nanomolar to subnanomolar range. The most potent ligands (4−7, 9, 13−27)
stimulated steroid biosynthesis in rat C6 glioma cells with a potency similar to or higher than
that of classical ligands. The SARs of this new class of compounds are discussed.