Synthesis and evaluation of novel potent HCV NS5A inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 14, 2012, Pages 4864-4868

  Zhang, Hongwang ^a   Zhou, Longhu ^a   Amblard, Franck ^a   Shi, Junxing ^b   Bobeck, Drew R ^b   Tao, Sijia ^a   McBrayer, Tamara R ^b   Tharnish, Phillip M ^b   Whitaker, Tony ^b   Coats, Steven J ^b   Schinazi, Raymond F ^a  

^a EMORY UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b RFS Pharma LLC   (United States)

Author keywords

Antiviral; HCV; NS5A

Indexed keywords

ANTIVIRUS AGENT; CYTOCHROME P450; DACLATASVIR; NONSTRUCTURAL PROTEIN 5A; NONSTRUCTURAL PROTEIN 5A INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG POTENCY; DRUG SCREENING; DRUG STABILITY; DRUG SYNTHESIS; ENZYME INHIBITION; HEPATITIS C VIRUS; HUMAN; HUMAN CELL; HUMAN TISSUE; LIVER MICROSOME; NONHUMAN; PROTEIN TARGETING; REPLICON; VIRUS INHIBITION; VIRUS REPLICATION;

ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HEPACIVIRUS; HUMANS; MICROSOMES, LIVER; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP;

HEPATITIS C VIRUS;

EID: 84863481975     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.05.039     Document Type: Article

References (31)

1. J.T. Liang, and J.H. Hoofnagle Hepatitis C, Biomedical Research Reports 2000 Academic Press London, UK pp 185-203
2. D.R. Bobeck, R.F. Schinazi, and S.J. Coats Antivir. Ther. 15 2010 935
3. C. Sheridan Nat. Biotechnol. 29 2011 553
4. R.F. Schinazi, L. Bassit, and C. Gavegnano J. Viral Hepat. 17 2010 77
5. M.G. Katze, B. Kwieciszewski, D.R. Goodlett, C.M. Blakely, P. Neddermann, S.L. Tan, and R. Aebersold Virology 278 2000 501
6. J. Kim, D. Lee, and J. Choe Biochem. Biophys. Res. Commun. 257 1999 777
7. R.A. Fridell, D. Qiu, C. Wang, L. Valera, and M. Gao Antimicrob. Agents Chemother. 54 2010 3641
8. 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 2nd, 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
9. Sun, J.-H.; Gao, M.; O'Boyle, D. R., II; Lemm, J. A.; Roberts, S. B.; Belema, M.; Meanwell, N. A. PCT Int. Appl. 2012, WO 2012009394 A2 20120119.
10. Lopez, O. D.; St. Laurent, D. R.; Goodrich, J.; Romine, J. Lee; Serrano-Wu, M.; Yang, F-K.; Kakarla, R.; Yang, X.-J.; Qiu, Y.-P.; Snyder, L. B. U.S. Pat. Appl. Publ. 2011, US 20110294819 A1 20111201
11. Belema, M.; Romine, J. L.; Nguyen, V. N.; Wang, G.; Lopez, O. D.; St. Laurent, D. R.; Chen, Q.; Bender, J. A.; Yang, Z.; Hewawasam, P.; Xu, N.-N.; Meanwell, N. A.; Easter, J. A.; Su, B.-N.; Smith, M. J. U.S. Pat. Appl. Publ. 2011, US 20110286961 A1 20111124.
12. Belema, M.; Hewawasam, P. U.S. Pat. Appl. Publ. 2011, US 20110237636 A1 20110929.
13. Bender, J. A.; Hewawasam, P.; Kadow, J. F.; Lopez, O. D.; Meanwell, N. A.; Nguyen, V. N.; Romine, J. L.; Snyder, L. B.; St. Laurent, D. R.; Wang, G.; Xu, N.-N.; Belema, M. PCT Int. Appl. 2010, WO 2010117635 A1 20101014.
14. Belema, M.; Nguyen, V. N.; Serrano-Wu, M.; St. Laurent, D. R.; Qiu, Y.-P., Ding, M.; Meanwell, N. A.; Snyder, L. B. U.S. Pat. Appl. Publ. 2010, US 20100080772 A1 20100401.
15. Bachand, C.; Belema, M.; Deon, D. H.; Good, A. C.; Goodrich, J.; Hamann, L. G.; James, C. A.; Langley, D. R.; 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.-K.; Wang, G. PCT Int. Appl. 2008, WO 2008144380 A1 20081127.
16. Milbank, J. B. J.; Tran, T. D.; Wakenhut, F. PCT Int. Appl. 2011, WO 2011154871 A1 20111215.
17. Vandyck K.; Verschueren, W. G.; Raboisson, P. J.-M. B. PCT Int. Appl. 2012, WO 2012013643 A1 20120202.
18. Li, L.-P.; Zhong, M. PCT Int. Appl. 2011, WO 2011156543 A2 20111215.
19. Qiu, Y.-L.; Wang, C.; Ying, L.; Peng, X.-W.; Or, Y. S. PCT Int. Appl. 2010, WO 2010091413 A1 20100812.
20. Li, L.-P.; Zhong, M. PCT Int. Appl. 2011, WO 2011150243 A1 20111201.
21. Kim, S.; Gao, Q.; Yang, F.-K. U.S. Pat. Appl. Publ. 2010, US 20100158862 A1 20100624.
22. 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.-K.; Langley, D. R.; Wang, G.; Hamann, L. G. PCT Int. Appl. 2009, WO 2009102318 A1 20090820.
23. 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.-K., Langley, D. R.; Hamann, L. G. PCT Int. Appl. 2008, WO 2008021936 A2 20080221.
24. Belema, M.; Romine, J. L.; Nguyen, V. N.; Wang, G.; Lopez, O. D.; St. Laurent, D. R.; Chen, Q.; Bender, J. A.; Yang, Z.; Hewawasam, P.; Xu, N.-N.; Meanwell, N. A.; Easter, J. A.; Su, B.-N.; Smith, M. J. PCT Int. Appl. 2011, WO 2011075439 A1 20110623.
25. Corte, J. R.; Fang, T.; Decicco, C. P.; Pinto, D. J. P.; Rossi, K. A.; Hu, Z.-L.; Jeon, Y.; Quan, M. L.; Smallheer, J. M.; Wang, Y.-F.; Yang, W. PCT Int. Appl. 2011, WO 2011100401 A1 20110818.
26. T.R. Webb, and C. Eigenbrot J. Org. Chem. 56 1991 3009
27. S. Shrestha, B.R. Bhattarai, K.-H. Lee, and H. Cho Bioorg. Med. Chem. 15 2007 6535
28. For reviews on the CuAAC see: J.E. Hein, and V.V. Fokin Chem. Soc. Rev. 39 2010 1302
29. V. AragaoLeoneti, V.L. Campo, A.S. Gomes, R.A. Field, and I. Carvalho Tetrahedron 66 2010 9475
30. F. Amblard, J.H. Cho, and R.F. Schinazi Chem. Rev. 109 2009 4207
31. J.A. Lemm, D. O'Boyle II, M. Liu, P.T. Nower, R. Colonno, M.S. Deshpande, L.B. Snyder, S.W. Martin, D.R. St. Laurent, M.H. Serrano-Wu, J.L. Romine, N.A. Meanwell, and M. Gao J. Virol. 84 2010 482