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Evaluation of quinazoline analogues as glucocerebrosidase inhibitors with chaperone activity.

Journal of medicinal chemistry (2011-01-22)
Juan J Marugan, Wei Zheng, Omid Motabar, Noel Southall, Ehud Goldin, Wendy Westbroek, Barbara K Stubblefield, Ellen Sidransky, Ronald A Aungst, Wendy A Lea, Anton Simeonov, William Leister, Christopher P Austin
RESUMEN

Gaucher disease is a lysosomal storage disorder (LSD) caused by deficiency in the enzyme glucocerebrosidase (GC). Small molecule chaperones of protein folding and translocation have been proposed as a promising therapeutic approach to this LSD. Most small molecule chaperones described in the literature contain an iminosugar scaffold. Here we present the discovery and evaluation of a new series of GC inhibitors with a quinazoline core. We demonstrate that this series can improve the translocation of GC to the lysosome in patient-derived cells. To optimize this chemical series, systematic synthetic modifications were performed and the SAR was evaluated and compared using three different readouts of compound activity: enzymatic inhibition, enzyme thermostabilization, and lysosomal translocation of GC.

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N-Boc-1,2,3,6-tetrahydropyridine-4-boronic acid pinacol ester, 95%