Aryl methylene ketones and fluorinated methylene ketones as reversible inhibitors for severe acute respiratory syndrome (SARS) 3C-like proteinase

Bioorganic Chemistry

Volumn 36, Issue 5, 2008, Pages 229-240

  Zhang, Jianmin ^a   Huitema, Carly ^b   Niu, Chunying ^a   Yin, Jiang ^a   James, Michael N G ^a   Eltis, Lindsay D ^b   Vederas, John C ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

^b UNIVERSITY OF BRITISH COLUMBIA   (Canada)

Author keywords

3C like proteinase; Fluorinated ketones; Ketones; Reversible inhibitors; SARS coronavirus

Indexed keywords

CARBENE; CHYMOTRYPSIN; CYSTEINE PROTEINASE; KETONE;

ARTICLE; CHEMICAL STRUCTURE; DISEASE SEVERITY; PRIORITY JOURNAL; PROTEIN STRUCTURE; SEVERE ACUTE RESPIRATORY SYNDROME;

ANTIVIRAL AGENTS; BINDING SITES; CYSTEINE ENDOPEPTIDASES; FLUORINE; HYDROCARBONS, AROMATIC; KETONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEASE INHIBITORS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

SARS CORONAVIRUS;

EID: 51549115724     PISSN: 00452068     EISSN: 10902120     Source Type: Journal    
DOI: 10.1016/j.bioorg.2008.01.001     Document Type: Article

References (29)

1. Drosten C., Günther S., Preiser W., van der Werf S., Brodt H.-R., Becker S., Rabenau H., Panning M., Kolesnikova L., Fouchier R.A.M., Berger A., Burguière A.-M., Cinatl J., Eickmann M., Escriou N., Grywna K., Kramme S., Manuguerra J.-C., Müller S., Rickerts V., Stürmer M., Vieth S., Klenk H.-D., Osterhaus A.D.M.E., Schmitz H., and Doerr H.W. N. Engl. J. Med. 348 (2003) 1967-1976
2. Cheng V.C.C., Lau S.K.P., Woo P.C.Y., and Yuen K.Y. Clin. Microbiol. Rev. 20 (2007) 660-694
3. Ksiazek T.G., Erdman D., Goldsmith C.S., Zaki S.R., Peret T., Emery S., Tong S., Urbani C., Comer J.A., Lim W., Rollin P.E., Dowell S.F., Ling A.-E., Humphrey C.D., Shieh W.-J., Guarner J., Paddock C.D., Roca P., Fields B., DeRisi J., Yang J.-Y., Cox N., Hughes J.M., LeDuc J.W., Bellini W.J., and Anderson L.J. N. Engl. J. Med. 348 (2003) 1953-1966
4. Lee N., Hui D., Wu A., Chan P., Cameron P., Joynt G.M., Ahuja A., Yung M.Y., Leung C.B., To K.F., Lui S.F., Szeto C.C., Chung S., and Sung J.J.Y. N. Engl. J. Med. 348 (2003) 1986-1994
5. Anand K., Ziebuhr J., Wadhwani P., Mesturs J.R., and Hilgenfeld R. Science 300 (2003) 1763-1767
6. Yang H., Yang M., Ding Y., Liu Y., Lou Z., Zhou Z., Sun L., Mo L., Ye S., Pang H., Gao G., Anand K., Bartlam M., Hilgenfeld R., and Rao Z. Proc. Natl. Acad. Sci. USA 100 (2003) 13190-13195
7. Thiel V., Ivanov K.A., Putics A., Hertzig T., Schelle B., Bayer S., Weißbrich B., Snijder E.J., Rabenau H., Doerr H.W., and Ziebuhr J. J. Gen. Virol. 84 (2003) 2305-2315
8. Wu C.-Y., Jan J.-T., Ma S.-H., Kuo C.-J., Juan H.-F., Cheng Y.-S.E., Hsu H.-H., Huang H.-C., Wu D., Brik A., Liang F.-S., Liu R.-S., Fang J.-M., Chen S.-T., Liang P.-H., and Wong C.-H. Proc. Natl. Acad. Sci. USA 101 (2004) 13190-13195
9. Bacha U., Barrila J., Velazquez-Campoy A., Leavitt S.A., and Freire E. Biochemistry 43 (2004) 4906-4912
10. Blanchard J.E., Elowe N.H., Fortin P.D., Huitema C., Cechetto J.D., Eltis L.D., and Brown E.D. Chem. Biol. 11 (2004) 1445-1453
11. Jain R.P., Pettersson H.I., Zhang J., Aull K.D., Fortin P.D., Huitema C., Eltis L.D., Parrish J.C., James M.N.G., Wishart D.S., and Vederas J.C. J. Med. Chem. 47 (2004) 6113-6116
12. Zhang J., Pettersson H.I., Huitema C., Niu C., Yin J., James M.N.G., Eltis L.D., and Vederas J.C. J. Med. Chem. 50 (2007) 1850-1864
13. Ghosh A.K., Xi K., Ratia K., Santarsiero B.D., Fu W., Harcourt B.H., Rota P.A., Baker S.C., Johnson M.E., and Mesecar A.D. J. Med. Chem. 48 (2005) 6767-6771
14. Ghosh A.K., Xi K., Grum-Tokars V., Xu X., Ratia K., Fu W., Houser K.V., Baker S.C., Johnson M.E., and Mesecar A.D. Bioorg. Med. Chem. Lett. 17 (2007) 5876-5880
15. Shie J.J., Fang J.M., Kuo T.H., Kuo C.J., Liang P.H., Huang H.J., Wu Y.T., Jan J.T., Cheng Y.S.E., and Wong C.H. Bioorg. Med. Chem. 13 (2005) 5240-5252
16. Shie J.-J., Fang J.-M., Kuo C.-J., Kuo T.-H., Liang P.-H., Huang H.-J., Yang W.-B., Lin C.-H., Chen J.-L., Wu Y.-T., and Wong C.-H. J. Med. Chem. 48 (2004) 4469-4473
17. Wu C.Y., King K.-Y., Kuo C.-J., Fang J.-M., Wu Y.-T., Ho M.-Y., Liao C.-L., Shie J.-J., Liang P.-H., and Wong C.-H. Chem. Biol. 13 (2006) 261-268
18. Silva A.M., Cachau R.E., Sham H.L., and Erickson J.W. J. Mol. Biol. 255 (1996) 321-334
19. Sweeney J.B., Tavassoli A., Carter N.B., and Hayes J.F. Tetrahedron 58 (2002) 10113-10126
20. Thompson W.J., and Gaudino J. J. Org. Chem. 49 (1984) 5237-5243
21. Borredon M.E., Delmas M., and Gaset A. Tetrahedron 43 (1987) 3945-3954
22. Jensen H.H., Lyngbye L., Jensen A., and Bols M. Chem. Eur. J. 8 (2002) 1218-1226
23. Abramovitch R.A., and Rogers R.B. J. Org. Chem. 39 (1974) 1802-1805
24. Bachman G.B., and Micucci D.D. J. Am. Chem. Soc. 39 (1948) 1802-1805
25. Müller P., and Chappellet S. Helv. Chim. Acta 88 (2005) 1010-1021
26. Prager R.H., Smith J.A., Weber B., and Williams C.M. J. Chem. Soc., Perkin Trans. 1. 17 (1997) 2665-2672
27. Silverman R.B. The Organic Chemistry of Enzyme-Catalyzed Reactions (2000), Academic Press, New York 15-30 Chapter 1
28. Niu C., Yin J., Zhang J., Vederas J.C., and James M.N.G. Bioorg. Med. Chem. 16 (2008) 293-302
29. Lu I.-L., Mahindroo N., Liang P.-H., Peng Y.-H., Kuo C.-J., Tsai K.-C., Hsieh H.-P., Chao Y.-S., and Wu S.-Y. J. Med. Chem. 49 (2006) 5154-5161