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Discovery of a Novel Series of Imidazopyrazine Derivatives as Potent SHP2 Allosteric Inhibitors

Esther Torrente, Valentina Fodale, A Ciammaichella, Federica Ferrigno, Jesus M. Ontoria, Simona Ponzi, Ilaria Rossetti, Alessio Sferrazza, Jérôme Amaudrut, Antonino Missineo, Simone Esposito, Simone Palombo, Martina Nibbio, Mauro Cerretani, Monica Bisbocci, Antonella Cellucci, Annalise Di Marco, Cristina Alli, Vincenzo Pucci, Carlo Toniatti, Alessia Petrocchi

2023ACS Medicinal Chemistry Letters20 citationsDOIOpen Access PDF

Abstract

Protein tyrosine phosphatase SHP2 is an oncogenic protein that can regulate different cytokine receptor and receptor tyrosine kinase signaling pathways. We report here the identification of a novel series of SHP2 allosteric inhibitors having an imidazopyrazine 6,5-fused heterocyclic system as the central scaffold that displays good potency in enzymatic and cellular assays. SAR studies led to the identification of compound 8, a highly potent SHP2 allosteric inhibitor. X-ray studies showed novel stabilizing interactions with respect to known SHP2 inhibitors. Subsequent optimization allowed us to identify analogue 10, which possesses excellent potency and a promising PK profile in rodents.

Topics & Concepts

Allosteric regulationProtein tyrosine phosphatasePotencyDrug discoveryChemistryReceptor tyrosine kinaseComputational biologyEnzymeTyrosine kinaseKinasePhosphataseScaffold proteinSignal transductionBiochemistryPharmacologyBiologyIn vitroProtein Tyrosine PhosphatasesGalectins and Cancer BiologyBioactive Compounds and Antitumor Agents
Discovery of a Novel Series of Imidazopyrazine Derivatives as Potent SHP2 Allosteric Inhibitors | Litcius