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ID: ALA1143198

Journal: Bioorg Med Chem Lett

Title: Potent, nonpeptide inhibitors of human mast cell tryptase. Synthesis and biological evaluation of novel spirocyclic piperidine amide derivatives.

Authors: Costanzo MJ, Yabut SC, Zhang HC, White KB, de Garavilla L, Wang Y, Minor LK, Tounge BA, Barnakov AN, Lewandowski F, Milligan C, Spurlino JC, Abraham WM, Boswell-Smith V, Page CP, Maryanoff BE.

Abstract: We have explored a series of spirocyclic piperidine amide derivatives (5) as tryptase inhibitors. Thus, 4 (JNJ-27390467) was identified as a potent, selective tryptase inhibitor with oral efficacy in two animal models of airway inflammation (sheep and guinea pig asthma models). An X-ray co-crystal structure of 4 x tryptase revealed a hydrophobic pocket in the enzyme's active site, which is induced by the phenylethynyl group and is comprised of amino acid residues from two different monomers of the tetrameric protein.

CiteXplore: 18272363

DOI: 10.1016/j.bmcl.2008.01.093