P1 phenethyl peptide boronic acid inhibitors of HCVNS3 protease

被引:55
作者
Priestley, ES [1 ]
De Lucca, I [1 ]
Ghavimi, B [1 ]
Erickson-Viitanen, S [1 ]
Decicco, CP [1 ]
机构
[1] Bristol Myers Squibb Co, Pharmaceut Res Inst, Expt Stn, Wilmington, DE 19880 USA
关键词
D O I
10.1016/S0960-894X(02)00682-0
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
A series of peptide boronic acids containing extended, hydrophobic P1 residues was prepared to probe the shallow, hydrophobic S1 region of HCV NS3 protease. The p-trifluoromethylphenethyl P1 substituent was identified as optimal with respect to inhibitor potency for NS3 and selectivity against elastase and chymotrypsin. (C) 2002 Published by Elsevier Science Ltd.
引用
收藏
页码:3199 / 3202
页数:4
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共 25 条
  • [1] The NS3/4A proteinase of the hepatitis C virus: unravelling structure and function of an unusual enzyme and a prime target for antiviral therapy
    Bartenschlager, R
    [J]. JOURNAL OF VIRAL HEPATITIS, 1999, 6 (03) : 165 - 181
  • [2] Replication of hepatitis C virus
    Bartenschlager, R
    Lohmann, V
    [J]. JOURNAL OF GENERAL VIROLOGY, 2000, 81 : 1631 - 1648
  • [3] HYDROBORATION .39. 1,3,2-BENZODIOXABOROLE (CATECHOLBORANE) AS A NEW HYDROBORATION REAGENT FOR ALKENES AND ALKYNES - GENERAL SYNTHESIS OF ALKANEBORONIC AND ALKENEBORONIC ACIDS AND ESTERS VIA HYDROBORATION - DIRECTIVE EFFECTS IN HYDROBORATION OF ALKENES AND ALKYNES WITH CATECHOLBORANE
    BROWN, HC
    GUPTA, SK
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (18) : 5249 - 5255
  • [4] CHARACTERIZATION OF A CLASS OF PEPTIDE BORONATES WITH NEUTRAL P1 SIDE-CHAINS AS HIGHLY SELECTIVE INHIBITORS OF THROMBIN
    DEADMAN, JJ
    ELGENDY, S
    GOODWIN, CA
    GREEN, D
    BABAN, JA
    PATEL, G
    SKORDALAKES, E
    CHINO, N
    CLAESON, G
    KAKKAR, VV
    SCULLY, MF
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 1995, 38 (09) : 1511 - 1522
  • [5] Inhibition of the hepatitis C virus NS3/4A protease - The crystal structures of two protease-inhibitor complexes
    Di Marco, S
    Rizzi, M
    Volpari, C
    Walsh, MA
    Narjes, F
    Colarusso, S
    De Francesco, R
    Matassa, VG
    Sollazzo, M
    [J]. JOURNAL OF BIOLOGICAL CHEMISTRY, 2000, 275 (10) : 7152 - 7157
  • [6] Potent peptide inhibitors of human hepatitis C virus NS3 protease are obtained by optimizing the cleavage products
    Ingallinella, P
    Altamura, S
    Bianchi, E
    Taliani, M
    Ingenito, R
    Cortese, R
    De Francesco, R
    Steinkühler, C
    Pessi, A
    [J]. BIOCHEMISTRY, 1998, 37 (25) : 8906 - 8914
  • [7] KETTNER CA, 1984, J BIOL CHEM, V259, P5106
  • [8] Crystal structure of the hepatitis C virus NS3 protease domain complexed with a synthetic NS4A cofactor peptide
    Kim, JL
    Morgenstern, KA
    Lin, C
    Fox, T
    Dwyer, MD
    Landro, JA
    Chambers, SP
    Markland, W
    Lepre, CA
    OMalley, ET
    Harbeson, SL
    Rice, CM
    Murcko, MA
    Caron, PR
    Thomson, JA
    [J]. CELL, 1996, 87 (02) : 343 - 355
  • [9] Transmission of hepatitis C by intrahepatic inoculation with transcribed RNA
    Kolykhalov, AA
    Agapov, EV
    Blight, KJ
    Mihalik, K
    Feinstone, SM
    Rice, CM
    [J]. SCIENCE, 1997, 277 (5325) : 570 - 574
  • [10] Hepatitis C virus-encoded enzymatic activities and conserved RNA elements in the 3′ nontranslated region are essential for virus replication in vivo
    Kolykhalov, AA
    Mihalik, K
    Feinstone, SM
    Rice, CM
    [J]. JOURNAL OF VIROLOGY, 2000, 74 (04) : 2046 - 2051