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ID: ALA3804828

Journal: J Med Chem

Title: 2,4,6-Triaminopyrimidine as a Novel Hinge Binder in a Series of PI3Kδ Selective Inhibitors.

Authors: Patel L, Chandrasekhar J, Evarts J, Haran AC, Ip C, Kaplan JA, Kim M, Koditek D, Lad L, Lepist EI, McGrath ME, Novikov N, Perreault S, Puri KD, Somoza JR, Steiner BH, Stevens KL, Therrien J, Treiberg J, Villaseñor AG, Yeung A, Phillips G.

Abstract: Inhibition of phosphoinositide 3-kinase δ (PI3Kδ) is an appealing target for several hematological malignancies and inflammatory diseases. Herein, we describe the discovery and optimization of a series of propeller shaped PI3Kδ inhibitors comprising a novel triaminopyrimidine hinge binder. Combinations of electronic and structural strategies were employed to mitigate aldehyde oxidase mediated metabolism. This medicinal chemistry effort culminated in the identification of 52, a potent and highly selective inhibitor of PI3Kδ that demonstrates efficacy in a rat model of arthritis.

CiteXplore: 26980109

DOI: 10.1021/acs.jmedchem.6b00213