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ID: ALA4190386

Journal: Bioorg Med Chem Lett

Title: Discovery of 6-(pyrimidin-5-ylmethyl)quinoline-8-carboxamide negative allosteric modulators of metabotropic glutamate receptor subtype 5.

Authors: Felts AS, Rodriguez AL, Morrison RD, Blobaum AL, Byers FW, Daniels JS, Niswender CM, Conn PJ, Lindsley CW, Emmitte KA.

Abstract: Based on previous work that established fused heterocycles as viable alternatives for the picolinamide core of our lead series of mGlu5 negative allosteric modulators (NAMs), we designed a novel series of 6-(pyrimidin-5-ylmethyl)quinoline-8-carboxamide mGlu5 NAMs. These new quinoline derivatives also contained carbon linkers as replacements for the diaryl ether oxygen atom common to our previously published chemotypes. Compounds were evaluated in a cell-based functional mGlu5 assay, and an exemplar analog 27 was >60-fold selective versus the other seven mGlu receptors. Selected compounds were also studied in metabolic stability assays in rat and human S9 hepatic fractions and exhibited a mixture of P450- and non-P450-mediated metabolism.

CiteXplore: 29705142

DOI: 10.1016/j.bmcl.2018.04.053