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Discovery and SAR exploration of a novel series of imidazo[4,5-b]pyrazin-2-ones as potent and selective mTOR kinase inhibitors.

Bioorganic & medicinal chemistry letters (2011-10-08)
Deborah S Mortensen, Sophie M Perrin-Ninkovic, Roy Harris, Branden G S Lee, Graziella Shevlin, Matt Hickman, Gody Khambatta, Rene R Bisonette, Kimberly E Fultz, Sabita Sankar
RÉSUMÉ

We report here the discovery of a novel series of selective mTOR kinase inhibitors. A series of imidazo[4,5-b]pyrazin-2-ones, represented by screening hit 1, was developed into lead compounds with excellent mTOR potency and exquisite kinase selectivity. Potent compounds from this series show >1000-fold selectivity over the related PI3Kα lipid kinase. Further, compounds such as 2 achieve mTOR pathway inhibition, blocking both mTORC1 and mTORC2 signaling, in PC3 cancer cells as measured by inhibition of pS6 and pAkt (S473).

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Sigma-Aldrich
Phenylboronic acid, 95%
Sigma-Aldrich
4-(1HTetrazol-5-yl)phenylboronic acid