Synthesis and evaluation of novel α-amino cyclic boronates as inhibitors of HCV NS3 protease

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 12, 2010, Pages 3550-3556

  Li, Xianfeng ^a   Zhang, Yong Kang ^a   Liu, Yang ^a   Ding, Charles Z ^a   Li, Qun ^a   Zhou, Yasheen ^a   Plattner, Jacob J ^a   Baker, Stephen J ^a   Qian, Xuelei ^b   Fan, Dazhong ^b   Liao, Liang ^b   Ni, Zhi Jie ^b   White, Gemma V ^c   Mordaunt, Jackie E ^c   Lazarides, Linos X ^c   Slater, Martin J ^c   Jarvest, Richard L ^c   Thommes, Pia ^c   Ellis, Malcolm ^c   Edge, Colin M ^c   Hubbard, Julia A ^c   Somers, Don ^c   Rowland, Paul ^c   Nassau, Pamela ^c   McDowell, Bill ^c   Skarzynski, Tadeusz J ^c   Kazmierski, Wieslaw M ^d   Grimes, Richard M ^d   Wright, Lois L ^d   Smith, Gary K ^d   Zou, Wuxin ^e   Wright, Jon ^e   Pennicott, Lewis E ^f   more..

^a PFIZER INC   (United States)

^b Acme Bioscience Inc   (United States)

^c GLAXOSMITHKLINE   (United Kingdom)

^d GLAXOSMITHKLINE   (United States)

^e BioDuro LLC   (China)

^f SussChem Ltd   (United Kingdom)

Author keywords

Cyclic boronate; HCV NS3; Hepatitis C; Protease inhibitor

Indexed keywords

ALPHA AMINO CYCLIC BORONATE INHIBITOR; ANTIVIRUS AGENT; BOCEPREVIR; HYDROXYL GROUP; NONSTRUCTURAL PROTEIN 3; SERINE; TELAPREVIR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVE SITE; HEPATITIS C VIRUS; NONHUMAN; STRUCTURE ACTIVITY RELATION;

BORONIC ACIDS; CATALYTIC DOMAIN; DRUG DESIGN; HEPACIVIRUS; MOLECULAR STRUCTURE; SERINE; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL NONSTRUCTURAL PROTEINS;

HEPATITIS C VIRUS;

EID: 77954216049     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.04.129     Document Type: Article

References (42)

1. F. Zoulim, M. Chevallier, M. Maynard, and C. Trepo Rev. Med. Virol. 13 2003 57
2. B.L. Pearlman Am. J. Med. 117 2004 344
3. M.W. Fried Hepatology 36 2002 S237
4. For recent reviews see: J.A. Thomson, and R.B. Perni Curr. Opin. Drug Discov. Dev. 9 2006 606
5. F.G. Njoroge, K.X. Chen, N.-Y. Shih, and J. Piwinski J. Acc. Chem. Res. 41 2008 50
6. Z.-J. Ni, and A.S. Wagman Curr. Opin. Drug Discov. Dev. 7 2004 446
7. N. Goudreau, and M. Llins-Brunet Expert Opin. Investig. Drugs 14 2005 1129
8. Y. Yan, Y. Li, S. Munshi, V. Sardana, J.L. Cole, M. Sardana, C. Steinkuehler, L. Tomei, R. De Francesco, L.C. Kuo, and Z. Chen Protein Sci. 7 1998 837
9. R.A. Love, H.E. Parge, J.A. Wickersham, Z. Hostomsky, N. Habuka, E.W. Moomaw, T. Adachi, and Z. Hostomska Cell 87 1996 331
10. M. Llins-Brunet, M.D. Bailey, G. Bolger, C. Brochu, A.M. Faucher, J.M. Ferland, M. Garneau, E. Ghiro, V. Gorys, C. Grand-Maître, T. Halmos, N. Lapeyre-Paquette, F. Liard, M. Poirier, M. Rhéaume, Y.S. Tsantrizos, and D. Lamarre J. Med. Chem. 47 2004 1605
11. R.B. Perni, S.J. Almquist, R.A. Byrn, G. Chandorkar, P.R. Chaturvedi, L.F. Courtney, C.J. Decker, K. Dinehart, C.A. Gates, S.L. Harbeson, A. Heiser, G. Kalkeri, E. Kolaczkowski, K. Lin, Y.P. Luong, B.G. Rao, W.P. Taylor, J.A. Thomson, R.D. Tung, Y. Wei, A.D. Kwong, and C. Lin Antimicrob. Agents Chemother. 50 2006 899
12. S. Venkatraman, S.L. Bogen, A. Arasappan, F. Bennett, K. Chen, E. Jao, Y.T. Liu, R. Lovey, S. Hendrata, Y. Huang, W. Pan, T. Parekh, P. Pinto, V. Popov, R. Pike, S. Ruan, B. Santhanam, B. Vibulbhan, W. Wu, W. Yang, J. Kong, X. Liang, J. Wong, R. Liu, N. Butkiewicz, R. Chase, A. Hart, S. Agrawal, P. Ingravallo, J. Pichardo, R. Kong, B. Baroudy, B. Malcolm, Z. Guo, A. Prongay, V. Madison, L. Broske, X. Cui, K.C. Cheng, Y. Hsieh, J.M. Brisson, D. Prelusky, W. Korfmacher, R. White, S. Bogdanowich-Knipp, A. Pavlovsky, P. Bradley, A.K. Saksena, A. Ganguly, J. Piwinski, V. Girijavallabhan, and F.G. Njoroge J. Med. Chem. 49 2006 6074
13. P. Raboisson, H. de Kock, A. Rosenquist, M. Nilsson, L. Salvador-Oden, T.I. Lin, N. Roue, V. Ivanov, H. Wähling, K. Wickström, E. Hamelink, M. Edlund, L. Vrang, S. Vendeville, W. Van de Vreken, D. McGowan, A. Tahri, L. Hu, C. Boutton, O. Lenz, F. Delouvroy, G. Pille, D. Surleraux, P. Wigerinck, B. Samuelsson, and K. Simmen Bioorg. Med. Chem. Lett. 18 2008 4853
14. S.D. Seiwert, S.W. Andrews, Y. Jiang, V. Serebryany, H. Tan, K. Kossen, P.T. Rajagopalan, S. Misialek, S.K. Stevens, A. Stoycheva, J. Hong, S.R. Lim, X. Qin, R. Rieger, K.R. Condroski, H. Zhang, M.G. Do, C. Lemieux, G.P. Hingorani, D.P. Hartley, J.A. Josey, L. Pan, L. Beigelman, and L.M. Blatt Antimicrob. Agents Chemother. 52 2008 4432
15. J.A. McCauley, C.J. McIntyre, M.T. Rudd, K.T. Nguyen, J.J. Romano, J.W. Butcher, K.F. Gilbert, K.J. Bush, M.K. Holloway, J. Swestock, B.L. Wan, S.S. Carroll, J.M. Dimuzio, D.J. Graham, S.W. Ludmerer, S.S. Mao, M.W. Stahlhut, C.M. Fandozzi, N. Trainor, D.B. Olsen, J.P. Vacca, and N.J.J. Liverton Med. Chem. 53 2010 2443
16. D.G. Hall Boronic Acids 2005 Wiley-VCH Weinheim, Germany
17. W. Yang, X. Gao, and B. Wang Med. Res. Rev. 23 2003 346
18. V.M. Dembitsky, A.A. Quntar, and M. Srebnik Mini-Rev. Med. Chem. 4 2004 1001
19. P.G. Richardson, C. Mitsiades, T. Hideshima, and K.C. Anderson Annu. Rev. Med. 57 2006 33
20. S. Venkatraman, W. Wu, A. Prongay, V. Girijavallabhan, and F.G. Njoroge Bioorg. Med. Chem. Lett. 19 2009 180
21. A. Boloor, D. Hanway, M. Joshi, D.T. Winn, G. Mendez, M. Walls, P. Wei, F. Qian, X. Zhang, Y. Zhang, M.E. Hepperle, X. Li, D.A. Campbell, and J.M. Betancort Bioorg. Med. Chem. Lett. 19 2009 5708
22. S. Jagannathan, T.P. Forsyth, and C.A. Kettner J. Org. Chem. 66 2001 6375
23. E.S. Priestley, I. De Lucca, B. Ghavimi, S. Erickson-Viitanen, and C.P. Decicco Bioorg. Med. Chem. Lett. 12 2002 3199
24. X. Zhang, A.C. Schmitt, W. Jiang, Z. Wasserman, and C.P. Decicco Bioorg. Med. Chem. Lett. 13 2003 1157
25. F.L. Rock, W. Mao, A. Yaremchuk, M. Tukalo, T. Crepin, H. Zhou, Y.-K. Zhang, V. Hernandez, T. Akama, S.J. Baker, J.J. Plattner, L. Shapiro, S.A. Martinis, S.J. Benkovic, S. Cusack, and M.R.K. Alley Science 316 2007 1759
26. S.J. Baker, Y.-K. Zhang, T. Akama, A. Lau, H. Zhou, V. Hernandez, W. Mao, M.R.K. Alley, V. Sanders, and J.J. Plattner J. Med. Chem. 49 2006 4447
27. T. Akama, S.J. Baker, Y.-K. Zhang, V. Hernandez, H. Zhou, V. Sanders, Y. Freund, R. Kimura, K.R. Maples, and J.J. Plattner Bioorg. Med. Chem. Lett. 19 2009 2129
28. D.M. Andrews, S.J. Carey, H. Chaignot, B.A. Coomber, N.M. Gray, S.L. Hind, P.S. Jones, G. Mills, J.E. Robinson, and M. Slater Org. Lett. 4 2002 4475
29. M.J. Slater, D.M. Andrews, G. Baker, S.S. Bethell, S. Carey, H. Chaignot, B. Clarke, B. Coomber, M. Ellis, A. Good, N. Gray, G. Hardy, P. Jones, G. Mills, and E. Robinson Bioorg. Med. Chem. Lett. 12 2002 3359
30. K.M. Sadhu, and D.S. Matteson Organometallics 4 1985 1687
31. S.M. Bauer, and R.W. Armstrong J. Am. Chem. Soc. 121 1999 6355
32. D.S. Matteson, and K.M. Sadhu J. Am. Chem. Soc. 105 1983 2077
33. D.S. Matteson, K.M. Sadhu, and M.L. Peterson J. Am. Chem. Soc. 108 1986 810
34. D.S. Matteson, and K.M. Sadhu J. Am. Chem. Soc. 102 1980 7588
35. Peptide acids a-b were purchased from Acme Bioscience, Inc. Peptide acids c-d were synthesized according to the procedures described in WO2009046098.
36. 3OD) δ 7.32 (m, 1H), 7.15 (d, 1H), 7.16-6.98 (m, 1H), 6.78 (d, 1H), 5.37 (s, 1H), 4.71-4.61 (m, 3H), 4.50-4.40 (m, 2H), 4.13 (d, 1H), 3.88-3.84 (m, 2H), 3.62-3.48 (br, 1H), 2.96 (d, 1H), 2.62-2.55 (m, 1H), 2.34-2.30 (m, 1H), 1.90-1.84 (m, 1H), 1.77-1.71 (m, 1H), 1.55-1.28 (m, 8H), 1.21-1.17 (m, 2H), 1.04 (s, 9H). For experimental details described the preparation of other α-amino cyclic boronates, see WO2009046098. All final compounds were found to be stable after over 1 year of storage in air.
37. Compounds were assayed in the fluorescence enzymatic assay. Conditions: 100 nM enzyme (1a domain), 30 μM NS4A, 5 μM 5-FAM-EDVVP-Pra-SMSE-K(5- TAMRA) enzyme substrate in 50 mM Hepes, 300 mM NaCl, 20% glycerol, 2 mM DTT and 0.1% NP40. Wavelengths of 485 ex and 535 em were used on a Molecular Devices plate reader to measure initial rates.
38. H. Ding, and W. Zhou Youji Huaxue 3 1981 178
39. W. Zhou, W. Lo, G. Zhang, H. Ding, and S. Liang J. Organomet. Chem. 387 1990 131
40. M.J. Slater, E.M. Amphlett, D.M. Andrews, P. Bamborough, S.J. Carey, M.R. Johnson, P.S. Jones, G. Mills, N.R. Parry, D.O. Somers, A.J. Stewart, and T. Skarzynski Org. Lett. 5 2003 4627
41. (a) The X-ray coordinates of compound 8d with HCV NS3 protease have been deposited in the Protein Data Bank (PDB code 2xcn ); (b) the X-ray coordinates of compound 8d with HCV NS3 mutant S139A have been deposited in the Protein Data Bank (PDB code 2xcf ).
42. V. Lohmann, F. Korner, J.-O. Koch, U. Herian, L. Theilman, and R. Batenschlager Science 285 1999 110