Towards the second generation of Boceprevir: Dithianes as an alternative P2 substituent for 2,2-dimethyl cycloproyl proline in HCV NS3 protease inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 5, 2010, Pages 1689-1692

  Nair, Latha G ^a   Bogen, Stephane ^a   Ruan, Sumei ^a   Pan, Weidong ^a   Pike, Russel ^a   Tong, Xiao ^a   Cheng, Kuo Chi ^a   Guo, Zhuyan ^a   Doll, Ronald J ^a   Njoroge, F George ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Dithianes; Glutarimides; HCV protease

Indexed keywords

(1,2,5) 6,6 DIMETHYL 3 AZABICYCLO[3.1.0]HEXANE 2 CARBOXYLIC ACID; 1,4 DITHIA 7 AZASPIRO[4.4]NONANE 8 CARBOXYLIC ACID; 2,2 DIMETHYL CYCLOPROYL PROLINE; ANTIVIRUS AGENT; BOCEPREVIR; NONSTRUCTURAL PROTEIN 3; PROTEIN P2; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; DRUG EXPOSURE; DRUG SYNTHESIS; HEPATITIS C VIRUS; NONHUMAN; RAT; STRUCTURE ACTIVITY RELATION;

ANIMALS; ANTIVIRAL AGENTS; BINDING SITES; COMPUTER SIMULATION; HUMANS; PROLINE; PROTEASE INHIBITORS; QUINOLIZINES; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFUR COMPOUNDS; VIRAL NONSTRUCTURAL PROTEINS;

HEPATITIS C VIRUS; RATTUS;

EID: 76649110186     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.01.037     Document Type: Article

References (49)

1. Cohen J. Science 285 (1999) 26-30
2. Alter M.J., Cresson-Moran D., Nanina O.V., McMullan G.M., GAO F., Moyer L.A., Maslow R.A., and Margolis H.S.N. Engl. J. Med. 341 (1999) 556-562
3. Cuthbert J.A. Clint. Microbial. Rev. 7 (1994) 505-532
4. Monte A., and Wright T.L. Semen. Once. (2001) 441
5. Neumann A.U., Lam N.P., Datary H., Retch D.R., Wiley T.E., Leyden T.J., and Per Elson A.S. Science 282 (1998) 103-107
6. Rosen H.R., and Retch D.R. Mol. Med. Today 5 (1999) 393-399
7. Di Bisceglie A.M., McHutchison J., and Rice C.M. Hepatology 35 (2002) 224-231
8. Lindenbach B.D., and Rice C.M. Nature 436 (2005) 933-938
9. Kolykhalov A.A., Mihalik K., Feinstone S.M., and Rice C.M. J. Virol. 74 (2000) 2046-2051
10. Lesk A.M., and Fordham W.D. J. Mol. Bio. 258 (1996) 501-537
11. De Francesco R., and Steinkuhler C. Curr. Top. Microbiol. Immunol. 242 (2000) 149-169
12. Yan Y., Li Y., Munshi S., Sardana V., Cole J.L., Sardana M., Steinkuehler C., Tomei L., De Francesco R., Kuo L.C., and Chen Z. Protein Sci. 7 (1998) 837-847
13. Di Marco S., Rizzi M., Volpari C., Walsh M.A., Narjes F., Colarusso S., De Francesco R., Matassa V.G., and Sollazzo M. J. Biol. Chem. 275 (2000) 7152-7157
14. De Francesco R., and Migliaccio G. Nature 436 (2005) 953-960
15. Tan S.-L., He Y., Huang Y., and Gale Jr. M. Curr. Opin. Pharmacol. 4 (2004) 465-470
16. Malancona S., Colarrusso S., Ontoria J.M., Marchetti A., Poma M., Stansfield I., Laufer R., Marco A.D., Taliani M., Verdirame M., Gonzalez-paz O., Matassa V.G., and Narjes F. Bioorg. Med. Chem. Lett. 14 (2004) 4575-4579
17. Llinas-Brunet M., Bailey M.D., Ghiro E., Gorys V., Halmos T., Poirier M., Rancourt J., and Goudreau N. J. Med. Chem. 47 (2004) 6584-6594
18. Andrews D.M., Barnes M.C., Dowle M.D., Hind S.L., Johnson M.R., Jones P.S., Mills G., Patikis A., Pateman T.J., Redfern T.J., Ed Robinson J., Slater M.J., and Trivedi. Org. Lett. 5 (2003) 4631-4634
19. Zhang X. Idrugs 5 (2002) 154-158
20. Dymock B.W. Expert Opin. Emerg. Drugs 6 (2001) 13-42
21. Dymock B.W., Jones P.S., and Wilson F.X. Antiviral. Chem. Chemother. 11 (2000) 79-96
22. Zhang R., Durkin J.P., and Windsor W.T. Bioorg. Med. Chem. Lett. 12 (2002) 1005-1008
23. Ingallinella P., Fattori D., Altamura S., Steinkuhler C., Koch U., Cicero D., Bazzo R., Cortese R., Bianchi E., and Pessi A. Biochemistry 41 (2002) 5483-5492
24. Beevers R., Carr M.G., Jones P.S., Jordan S., Kay P.B., Lazell R.C., and Raynham T.M. Bioorg. Med. Chem. Lett. 12 (2002) 641-643
25. Venderville S., Nilsson M., de Kock H., Lin T.-I., Antonov D., Classon B., Ayesa S., Ivanov V., Johansson P.-O., Kahnberg P., Eneroth A., Wikstrom K., Vrang L., Edlund M., Lindstrom S., Vreken W.V.De., McGowan D., Tahri A., Ku L., Lenz O., Delouvroy F., Dooren M.V., Kindermans N., Surleraux D., Wigerinck P., Rosenquist A., Samuelsson B., Simmen K., and Raboisson P. Biorg. Med. Chem. Lett. 18 (2008) 6189
26. For BILN-2061, see:. Lamarre D., Anderson P.C., Bailey M., Beaulieu P., Bolger G., Bonneau P., Bös M., Cameron D.R., Cartier M., Cordingley M.G., Faucher A.-M., Goudreau N., Kawai S.H., Kukolj G., Lagacé L., LaPlante S.R., Narjes H., Poupart M.-A., Rancourt J., Sentjens R.E., George T.S., Simoneau B., Steinmann G., Thibeault D., Tsantrizos Y.S., Weldon S.M., Yong C.-L., and Llinàs-Brunet M. Nature 426 (2003) 186-189
27. Tsantrizos Y.S., Bolger G., Bonneau P., Cameron D.R., Gordreau N., Kukolj G., LaPlante S.R., Llinas-Brunet M., Nar H., and Lamarre D. Angew. Chem., Int. Ed. 42 (2003) 1355-1360
28. For VX-950, see:. Yip Y., Victor F., Lamar J., Johnson R., Wang Q., May G., John I., Yumibe N., Wakulchik M., Munroe J., and Chen S.-H. Bio. Med. Chem. Lett. 14 (2004) 5007-5011
29. Perni, R. Gordon Research Conference, New London, New Hampshire, 2005, August 7-12.
30. MK-7009 referneces:. Anon. Nat. Rev. Drug Discovery 8 (2009) 11
31. Harper S., Ferrara M., Crescenzi B., Pompei M., Palumbi M.C., Di Muzio J.M., Donghi M., Fiore F., Koch U., Liverton N.J., Pesci S., Petrocchi A., Rowley M., Summa V., and Gardelli C. J. Med. Chem. 52 (2009) 4820-4837
32. For Boceprevir:. Venkatraman S., Bogen S., Arasappan A., Bennet F., Chen K., Jao E., Liu Y.-T., Lovey R., Hendreta S., Huang Y., Pan W., Parekh T., Pinto P., Popov V., Pike R., Ruan S., Santhanam B., Vibulbhan B., Wu W., Yang W., Kong J., Liang X., Wong J., Liu R., Butkiewicz N., Chase R., Hart A., Agrawal S., Ingravallo P., Pichardo J., Kong R., Baroudy B., Malcolm B., Guo Z., Prongay A., Madison V., Broske L., Cui X., Cheng K.-C., Hsieh T.Y., Brisson J.-M., Prelusky D., Korfmacher W., White R., Bogdanowich-Knipp S., Pavlovsky A., Bradley P., Saksena A.K., Ganguly A., Piwinski J., Girijavallabhan V., and Njoroge F.G. J. Med. Chem. 49 (2006) 6074
33. Smith E.M., Swiss G.F., Neustard B.R., Gold E.H., Sommer J.A., Brown A.D., and Deeter J.B. J. Org. Chem. 59 (1994) 4327-4331
34. Chen K.X., Arasappan A., Njoroge F.G., Vibulbhan B., Buevich A., Chan T.-M., and Girijavallabhan V. J. Org. Chem. 67 (2002) 2730-2733
35. Arasappan A., Chen K.X., Njoroge F.G., Parekh T.N., and Girijavallabhan V. J. Org. Chem. 67 (2002) 3923-3926
36. Pfitzner K.E., and Moffatt J.C. J. Am. Chem. Soc. 113 (1991) 7277-7287
37. Zhang R., Beyer B.M., Durkin J., Ingram R., Njoroge F.G., Windsor W.T., and Malcolm B.A. Anal. Biochem. 270 (1999) 268-275
38. Taremi S.S., Beyer B., Maher M., Yao N., Prosise W., Weber P.C., and Malcolm B.A. Protein Sci. 7 (1998) 2143
39. * and discussions, see: Morrison, J. F.; Walsh, C. T. In Adv. Enzymol., Meister, A., Ed.; Interscience: NY, 1988, Vol. 61, pp 201-301.
40. Chung v., Carroll A.R., Gray N.M., Parry N.R., Thommes P.A., Viner K.C., and D'Souza E.A. Antimicrob. Agents Chemother. 49 (2005) 1381-1390
41. Blight K.J., Kolykhalov A.A., and Rice C.M. Science 290 (2000) 1972-1974
42. Lohmann V., Körner F., Koch J.-O., Herian U., Theilmann L., and Bartenschlager R. Science 285 (1999) 110-113
43. Bogen S., Saksena A.K., Arasappan A., Gu H., Njoroge F.G., Girijavallabhan V., Pichardo J., Butkiewicz N., Prongay A., and Madison V. Biorg. Med. Chem. Lett. 15 (2005) 4515-4519
44. Bogen S., Saksena A., Bennett F., Chen K., Jao E., Liu Y.-T., Lovey R.G., Venkatraman S., Pan W., Parekh T., Pike R.E., Ruan S., Liu R., Baroundy B., Agrawal S., Chase R., Ingravallo P., Pichardo J., Prongay A., Brisson J.-M., Hsieh T.Y., Cheng K.-C., Kemp S.J., Levy O.E., Lim-Wilby M., Tamura S.Y., Saksena A.K., Girijavallabhan V., and Njoroge F.G. J. Med. Chem 49 (2006) 2750-2757
45. Tong X., Bogen S., Chase R., Girijavallabhan V., Guo Z., Njoroge F.G., Prongay A., Saksena A., Skelton A., Xia E., and Ralston R. Antiviral Res. (2008) 177-185
46. Arasappan A., Padilla A.I., Jao E., Bennett F., Bogen S.L., Chen K.X., Pike R.E., Sannigrahi M., Soares J., Venkatraman S., Vibulbhan B., Saksena A.K., Girijavallabhan V., Tong X., Cheng K.-C., and Njoroge F.G. J. Med. Chem. 52 (2009) 2806-2817
47. Chen K.X., Nair L., Vibulbhan B., Yang W., Arasappan A., Bogen S.L., Venkatraman S., Bennett F., Pan W., Blackman M.L., Padilla A.I., Prongay A., Cheng K.-C., Tong X., Shih N.-Y., and Njoroge F.G. J. Med. Chem. 52 (2009) 1370-1379
48. Venkatraman S., Blackman M., Wu W., Nair L., Arasappan A., Padilla A., Bogen S., Bennett F., Chen K., Pichardo J., Tong X., Prongay A., Cheng K.-C., Girijavallabhan V., and George N.F. Bioorg. Med. Chem. 17 (2009) 4486-4495
49. Unpublished results, Schering-Plough Research Institute.