Inhibition of hepatitis C virus NS5A by fluoro-olefin based γ-turn mimetics

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 8, 2012, Pages 2938-2942

  Chang, Wonsuk ^a   Mosley, Ralph T ^a   Bansal, Shalini ^a   Keilman, Meg ^a   Lam, Angela M ^a   Furman, Phillip A ^a   Otto, Michael J ^a   Sofia, Michael J ^a  

^a PHARMASSET INC   (United States)

Author keywords

Turn; Antiviral; HCV; Hepatitis C; NS5A; Peptidomimetics

Indexed keywords

NONSTRUCTURAL PROTEIN 5A; NONSTRUCTURAL PROTEIN 5A INHIBITOR; PEPTIDOMIMETIC AGENT; PROTEIN INHIBITOR; UNCLASSIFIED DRUG;

ANTIVIRAL ACTIVITY; ARTICLE; DRUG CYTOTOXICITY; DRUG POTENCY; DRUG STRUCTURE; DRUG TARGETING; HEPATITIS C VIRUS; HYDROGEN BOND; MATHEMATICAL MODEL; NONHUMAN;

ALKENES; FLUORINE; HEPACIVIRUS; HUMANS; HYDROGEN BONDING; MODELS, MOLECULAR; PEPTIDOMIMETICS; VIRAL NONSTRUCTURAL PROTEINS;

HEPATITIS C VIRUS;

EID: 84859440860     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.02.051     Document Type: Article

References (44)

1. F. Negro, and A. Alberti Liver Int. 31 2011 1
2. P.J. Pockros Expert Opin. Biol. Ther. 11 2011 1611
3. K. Garber Nat. Biotechnol. 29 2011 963
4. M.J. Sofia, W. Chang, P.A. Furman, R.T. Mosley, and B.S. Ross J. Med. Chem. 2012 10.1021/jm201384j
5. Nettles, R.; Chien, C.; Chung, E.; Persson, A.; Gao, M.; Belema, M.; Meanwell, N. A.; DeMicco, M. P.; Marbury, T. C.; Goldwater, R.; Northup, P.; Coumbis, J.; Kraft, W. K.; Charlton, M. R.; Lopez-Talavera, J. C.; Grasela, D. Abstract of Papers, 59th Annual Meeting of the American Association for the Study of Liver Diseases, San Francisco, CA; John Wiley & Sons Inc.: Malden, MA, 2008, Abstract LB12.
6. M. Gao, R.E. Nettles, M. Belema, L.B. Snyder, V.N. Nguyen, R.A. Fridell, M.H. Serrano-Wu, D.R. Langley, J.H. Sun, D.R. O'Boyle II, J.A. Lemm, C. Wang, J.O. Knipe, C. Chien, R.J. Colonno, D.M. Grasela, N.A. Meanwell, and L.G. Hamann Nature 465 2010 96
7. R.E. Nettles, M. Gao, M. Bifano, E. Chung, A. Persson, T.C. Marbury, R. Goldwater, M.P. DeMicco, M. Rodriguez-Torres, A. Vutikullird, E. Fuentes, E. Lawitz, J.C. Lopez-Talavera, and D.M. Grasela Hepatology 54 2011 1956
8. N.A. Meanwell, and M. Belema Annu. Rep. Med. Chem. 46 2011 263
9. P. Najarro, N. Mathews, and S. Cockerill S.-L. Tan, Y. He, Hepatitis C 2011 Caister Academic Press Norfolk, UK 271 292
10. D.G. Cordek, J.T. Bechtel, A.T. Maynard, W.M. Kazmierski, and C.E. Cameron Drugs Future 36 2011 691
11. Some recent patent applications on related NS5A inhibitors: (a) Bachand, C.; Belema, M.; Deon, D. H.; Good, A. C.; Goodrich, J.; James, C. A.; Lavoie, R.; Lopez, O. D.; Martel, A.; Meanwell, N. A.; Nguyen, V. N.; Romine, J. L.; Ruediger, E. H.; Snyder, L. B.; St. Laurent, D. R.; Yang, F.; Langley, D. R.; Wang, G.; Hamann, L. G. PCT Int. Appl. WO 2008021927, 2008;
12. (b) Guo, H.; Kato, D.; Kirschberg, T. A.; Liu, H.; Link, J. O.; Mitchell, M. L.; Parrish, J. P.; Squires, N.; Sun, J.; Taylor, J.; Bacon, E. M.; Canales, E.; Cho, A.; Cottell, J. J.; Desai, M. C.; Halcomb, R. L.; Krygowski, E. S.; Lazerwith, S. E.; Liu, Q.; Mackman, R.; Pyun, H.-J.; Saugier, J. H.; Trenkle, J. D.; Tse, W. C.; Vivian, R. W.; Schroeder, S. D.; Watkins, W. J.; Xu, L.; Yang, Z.-Y.; Kellar, T.; Sheng, X.; Clarke, M. O. H.; Chou, C.-H.; Graupe, M.; Jin, H.; Mcfadden, R.; Mish, M. R.; Metobo, S. E.; Phillips, B. W.; Venkataramani, C. PCT Int. Appl. WO 2010132601, 2010;
13. (c) Li, L.; Zhong, M. PCT Int. Appl. WO 2010065668, 2010;
14. (d) Degoey, D. A.; Kati, W. M.; Hutchins, C. W.; Donner, P. L.; Krueger, A. C.; Randolph, J. T.; Motter, C. E.; Nelson, L. T.; Patel, S. V.; Matulenko, M. A.; Keddy, R. G.; Jinkerson, T. K.; Soltwedel, T. N.; Hutchinson, D. K.; Flentge, C. A.; Wagner, R.; Maring, C. J.; Tufano, M. D.; Betebenner, D. A.; Rockway, T. W.; Liu, D.; Pratt, J. K.; Lavin, M. J.; Sarris, K.; Woller, K. R.; Wagaw, S. H.; Califano, J. C.; Li, W. PCT Int. Appl. WO 2010144646, 2010;
15. (e) Or, Y. S.; Peng, X.; Ying, L.; Ce, W.; Tang, D.; Qiu, Y.-L. PCT Int. Appl. WO 2010096462, 2010;
16. (f) Schmitz, F. U.; Rai, R.; Roberts, C. D.; Kazmierski, W.; Grimes, R. PCT Int. Appl. WO 2010062821, 2010;
17. (g) Rosenblum, S. B.; Chen, K. X.; Kozlowski, J. A.; Njoroge, F. G.; Coburn, C. A. PCT Int. Appl. WO 2010132538, 2010;
18. (h) Dousson, C. B.; Dukhan, D.; Parsy, C. C.; Pierra, C.; Alexandre, F.-R.; Brandt, G.; Da Costa, D.; Rahali, H.; Paparin, J.-L.; Derock, M.; Convard, T.; Surleraux, D. PCT Int. Appl. WO 2011075615, 2011.
19. Monte Carlo Multiple Minimum: G. Chang, W.C. Guida, and W.C. Still J. Am. Chem. Soc. 111 1989 4379
20. M. Saunders, K.N. Houk, Y.D. Wu, C.W. Still, M. Lipton, G. Chang, and W.C. Guida J. Am. Chem. Soc. 112 1990 1419
21. T.A. Halgren J. Comput. Chem. 20 1999 720
22. T.A. Halgren J. Comput. Chem. 20 1999 730
23. F.A. Etzkorn, and J.M. Travins A. Abell, Advances in Amino Acid Mimetics and Peptidomimetics Vol. 2 1999 Jai Press Inc. Stamford, CT 125 163
24. S. Couve-Bonnaire, D. Cahard, and X. Pannecoucke Org. Biomol. Chem. 5 2007 1151
25. J.T. Welch A. Tressaud, G. Haufe, Fluorine and Health 2008 Elsevier 699 735
26. P.A. Bartlett, and A. Otake J. Org. Chem. 60 1995 3107
27. J.T. Welch, J. Lin, L.G. Boros, B. DeCorte, K. Bergmann, and R. Gimi I. Ojima, J.R. McCarthy, J.T. Welch, Biomedical Frontiers of Fluorine Chemistry 1996 American Chemical Society Washington D.C. 129 142
28. J.T. Welch, and J. Lin Tetrahedron 52 1996 291
29. J. Lin, P.J. Toscano, and J.T. Welch Proc. Natl. Acad. Sci. U.S.A. 95 1998 14020
30. K. Zhao, D.S. Lim, T. Funaki, and J.T. Welch Bioorg. Med. Chem. Lett. 11 2003 207
31. P. Van der Veken, I. Kertesz, K. Senten, A. Haemers, and K. Augustyns Tetrahedron Lett. 44 2003 6231
32. P. Van der Veken, K. Senten, I. Kertesz, I. De Meester, A.-M. Lambeir, M.-B. Maes, S. Scharpe, A. Haemers, and K. Augustyns J. Med. Chem. 48 2005 1768
33. S.D. Edmondson, L. Wei, J. Xu, J. Shang, S. Xu, J. Pang, A. Chaudhary, D.C. Dean, H. He, B. Leiting, K.A. Lyons, R.A. Patel, S.B. Patel, G. Scapin, J.K. Wu, M.G. Beconi, N.A. Thornberry, and A.E. Weber Bioorg. Med. Chem. Lett. 18 2008 2409
34. T. Allmendinger, P. Furet, and E. Hungerbuehler Tetrahedron Lett. 31 1990 7297
35. T. Allmendinger, P. Furet, and E. Hungerbuehler Tetrahedron Lett. 31 1990 7031
36. R. Waelchli, R. Gamse, W. Bauer, H. Meigel, E. Lier, and J.H.M. Feyen Bioorg. Med. Chem. Lett. 6 1996 1151
37. N. Mase, A. Inoue, M. Nishio, and K. Takabe Bioorg. Med. Chem. Lett. 19 2009 3955
38. M.T. Robak, M.A. Herbage, and J.A. Ellman Chem. Rev. 110 2010 3600
39. J.A. Ellman, T.D. Owens, and T.P. Tang Acc. Chem. Res. 35 2002 984
40. C. Pierry, L. Zoute, P. Jubault, E. Pfund, T. Lequeux, D. Cahard, S. Couve-Bonnaire, and X. Pannecoucke Tetrahedron Lett. 50 2009 264
41. C. Pierry, D. Cahard, S. Couve-Bonnaire, and X. Pannecoucke Org. Biomol. Chem. 9 2011 2378
42. U. Schmitz, and S.-L. Tan Recent Pat. Anti-infect. Drug Discov. 3 2008 77
43. B.E. McKinney, and J.J. Urban J. Phys. Chem. A 114 2010 1123
44. J.A. Howard, W.J. Hoy, D. O'Hagan, and G.T. Smith Tetrahedron 52 1996 12613