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ID: ALA2375236

Journal: Bioorg Med Chem Lett

Title: Strategic use of conformational bias and structure based design to identify potent JAK3 inhibitors with improved selectivity against the JAK family and the kinome.

Authors: Lynch SM, DeVicente J, Hermann JC, Jaime-Figueroa S, Jin S, Kuglstatter A, Li H, Lovey A, Menke J, Niu L, Patel V, Roy D, Soth M, Steiner S, Tivitmahaisoon P, Vu MD, Yee C.

Abstract: Using a structure based design approach we have identified a series of indazole substituted pyrrolopyrazines, which are potent inhibitors of JAK3. Intramolecular electronic repulsion was used as a strategy to induce a strong conformational bias within the ligand. Compounds bearing this conformation participated in a favorable hydrophobic interaction with a cysteine residue in the JAK3 binding pocket, which imparted high selectivity versus the kinome and improved selectivity within the JAK family.

CiteXplore: 23540648

DOI: 10.1016/j.bmcl.2013.02.012