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ID: ALA1149226

Journal: Bioorg Med Chem Lett

Title: Inhibitors of hepatitis C virus NS3.4A protease. Part 3: P2 proline variants.

Authors: Perni RB, Farmer LJ, Cottrell KM, Court JJ, Courtney LF, Deininger DD, Gates CA, Harbeson SL, Kim JL, Lin C, Lin K, Luong YP, Maxwell JP, Murcko MA, Pitlik J, Rao BG, Schairer WC, Tung RD, Van Drie JH, Wilson K, Thomson JA.

Abstract: We recently described the identification of an optimized alpha-ketoamide warhead for our series of HCV NS3.4A inhibitors. We report herein a series of HCV protease inhibitors incorporating 3-alkyl-substituted prolines in P(2). These compounds show exceptional enzymatic and cellular potency given their relatively small size. The marked enhancement of activity of these 3-substituted proline derivatives relative to previously reported 4-hydroxyproline derivatives constitutes additional evidence for the importance of the S(2) binding pocket as the defining pharmacophore for inhibition of the NS3.4A enzyme.

CiteXplore: 15050632

DOI: 10.1016/j.bmcl.2004.01.078