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ID: ALA1147169

Journal: Bioorg Med Chem Lett

Title: From pyrroles to 1-oxo-2,3,4,9-tetrahydro-1H-beta-carbolines: a new class of orally bioavailable mGluR1 antagonists.

Authors: Di Fabio R, Micheli F, Alvaro G, Cavanni P, Donati D, Gagliardi T, Fontana G, Giovannini R, Maffeis M, Mingardi A, Tranquillini ME, Vitulli G.

Abstract: Exploiting the SAR of the known pyrrole derivatives, a new class of mGluR1 antagonists was designed by replacement of the pyrrole core with an indole scaffold and consequent cyclization of the C-2 position into a tricyclic beta-carboline template. The appropriate exploration of the position C-6 with a combination of H-bond acceptor groups coupled with bulky/lipophilic moieties led to the discovery of a new series of mGluR1 antagonists. These compounds exhibited a non-competitive behavior, excellent pharmacokinetic properties, and good in vivo activity in animal models of acute and chronic pain, after oral administration.

CiteXplore: 17276684

DOI: 10.1016/j.bmcl.2007.01.055