Design and synthesis of new tripeptide-type SARS-CoV 3CL protease inhibitors containing an electrophilic arylketone moiety

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 2, 2013, Pages 412-424

  Konno, Sho ^a   Thanigaimalai, Pillaiyar ^a   Yamamoto, Takehito ^a   Nakada, Kiyohiko ^a   Kakiuchi, Rie ^a   Takayama, Kentaro ^a   Yamazaki, Yuri ^a   Yakushiji, Fumika ^a   Akaji, Kenichi ^b   Kiso, Yoshiaki ^b   Kawasaki, Yuko ^c   Chen, Shen En ^c   Freire, Ernesto ^c   Hayashi, Yoshio ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

^b KYOTO PHARMACEUTICAL UNIVERSITY   (Japan)

^c JOHNS HOPKINS UNIVERSITY   (United States)

Author keywords

Cysteine protease inhibitors; Docking study; Peptidomimetics; SARS; SARS CoV 3CL protease

Indexed keywords

2 (2 ACETAMIDO 3 METHYLBUTANAMIDO) 4 METHYL N [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL]PENTANAMIDE; 2,2 DIMETHYL 1 [[[1 OXO 1 (THIAZOL 2 YL) 3 (1 TOSYL 1H IMIDAZOL 4 YL)PROPAN 2 YL]AMINO]OXY]PROPAN 1 ONE; 4 METHYL 2 [3 METHYL 2 (2 PHENOXYACETAMIDO)BUTANAMIDO] N [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL]PENTANAMIDE; 4 METHYL 2 [3 METHYL 2 (3 PHENYLPROPANAMIDO)BUTANAMIDO] N [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL]PENTANAMIDE; 4 NITROBENZYL [3 METHYL 1 [[4 METHYL 1 OXO 1 [(1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL)AMINO]PENTAN 2 YL]AMINO] 1 OXOBUTAN 2 YL]CARBAMATE; BENZOTHIAZOLE; BENZYL 1 [1 [[1 [[1 (4,5 DIMETHYLTHIAZOL 2 YL) 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]AMINO] 4 METHYL 1 OXOPENTAN 2 YL]AMINO] 3 METHYL 1 OXOBUTAN 2 YL]CARBAMATE; BENZYL 1 [1 [[1 [[1 (BENZO[D]THIAZOL 2 YL) 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]AMINO] 4 METHYL 1 OXOPENTAN 2 YL]AMINO] 3 METHYL 1 OXOBUTAN 2 YL]CARBAMATE; CHYMOTRYPSIN LIKE PROTEASE; ISOBUTYL [3 METHYL 1 [[4 METHYL 1 OXO 1 [(1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL)AMINO]PENTAN 2 YL]AMINO] 1 OXOBUTAN 2 YL]CARBAMATE; N [1 (BENZO[D]THIAZOL 2YL) 1 OXO 3 (2 OXOPYROLIDIN 3 YL)PROPAN 2 YL] 2 [2 [2 (2 METHOXYPHENOXY)ACETAMIDO] 3 METHYLBUTANAMIDO] 4 METHYLPENTANAMIDE; N [1 (BENZO[D]THIAZOL 2YL) 1 OXO 3 (2 OXOPYROLIDIN 3 YL)PROPAN 2 YL] 2 [2 [2 (3 METHOXYPHENOXY)ACETAMIDO] 3 METHYLBUTANAMIDO] 4 METHYLPENTANAMIDE; N [1 (BENZO[D]THIAZOL 2YL) 1 OXO 3 (2 OXOPYROLIDIN 3 YL)PROPAN 2 YL] 2 [2 [2 (4 METHOXYPHENOXY)ACETAMIDO] 3 METHYLBUTANAMIDO] 4 METHYLPENTANAMIDE; N [1 (BENZO[D]THIAZOL 2YL) 1 OXO 3 (2 OXOPYROLIDIN 3 YL)PROPAN 2 YL] 4 METHYL 2 [3 METHYL 2 (2 PHENOXYACETAMIDO)BUTANAMIDO]PENTAMIDE; NEOPENTYL [3 METHYL 1 [[4 METHYL 1 OXO 1 [(1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL)AMINO]PENTAN 2 YL]AMINO] 1 OXOBUTAN 2 YL]CARBAMATE; PHENYL [3 METHYL 1 [[4 METHYL 1 OXO 1 [(1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL)AMINO]PENTAN 2 YL]AMINO] 1 OXOBUTAN 2 YL]CARBAMATE; PROTEINASE; PROTEINASE INHIBITOR; TERT BUTYL [1 (5 METHYLTHIAZOL 2 YL) 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 (BENZO[D]THIAZOL 2 YL) 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 [5 (2 METHOXYPHENYL)THIAZOL 2 YL] 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 [5 (4 CHLOROPHENYL)THIAZOL 2 YL] 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 [5 (4 METHOXYPHENYL)THIAZOL 2 YL] 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 [5 (NAPHTHALEN 2 YL)THIAZOL 2 YL] 1 OXO 3 (2 OXOPYRROLIDIN 3 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (5 PHENYLTHIAZOL 2 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 (THIAZOL 2 YL)PROPAN 2 YL]CARBAMATE; TERT BUTYL [1 OXO 3 (2 OXOPYRROLIDIN 3 YL) 1 [5 (4 TOLYL)THIAZOL 2 YL]PROPAN 2 YL ]CARBAMATE; TERT BUTYL [3 (4,5 DIHYDRO 1H IMIDAZOL 4 YL) 1 (5 METHYLTHIAZOL 2 YL) 1 OXOPROPAN 2 YL] CARBAMATE; THIAZOLE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; DRUG BINDING; DRUG DESIGN; DRUG DEVELOPMENT; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; HYDROPHOBICITY; IC 50; MOLECULAR DOCKING; SARS CORONAVIRUS; STEREOCHEMISTRY; VIRUS INHIBITION;

BENZOTHIAZOLES; BINDING SITES; CYSTEINE ENDOPEPTIDASES; DRUG DESIGN; HYDROGEN BONDING; MOLECULAR DOCKING SIMULATION; OLIGOPEPTIDES; PROTEASE INHIBITORS; PROTEIN BINDING; PROTEIN STRUCTURE, TERTIARY; SARS VIRUS; STRUCTURE-ACTIVITY RELATIONSHIP; VIRAL PROTEINS;

SARS CORONAVIRUS;

EID: 84871634551     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.11.017     Document Type: Article

References (31)

1. T.G. Ksiazek, D. Erdman, C.S. Goldsmith, S.R. Zaki, T. Peret, S. Emery, S. Tong, C. Urbani, J.A. Comer, W. Lim, P.E. Rollin, S.F. Dowell, A.E. Ling, C.D. Humphrey, W.J. Shieh, J. Guarner, C.D. Paddock, P. Roca, B. Fields, J. DeRisi, J.Y. Yang, N. Cox, J.M. Hughes, J.W. LeDuc, W.J. Bellini, and L.J. Anderson N. Engl. J. Med. 348 2003 1953
2. C. Drosten, S. Gunther, W. Preiser, S. van der Werf, H.R. Brodt, S. Becker, H. Rabenau, M. Panning, L. Kolesnikova, R.A.M. Fouchier, A. Berger, A.M. Burguiere, J. Cinatl, M. Eickmann, N. Escriou, K. Grywna, S. Kramme, J.-C. Manuguerra, S. Muller, V. Rickerts, M. Sturmer, S. Vieth, H.D. Klenk, A.D.M.E. Osterhaus, H. Schmitz, and H.W. Doerr N. Engl. J. Med. 348 2003 1967
3. J.S. Peiris, S.T. Lai, L.L. Poon, Y. Guan, L.Y. Yam, W. Lim, J. Nicholls, W.K. Yee, W.W. Yan, M.T. Cheung, V.C. Cheng, K.H. Chan, D.N. Tsang, R.W. Yung, T.K. Ng, and K.Y. Yuen Lancet 361 2003 1319 and references therein
4. World Health Organization, Communicable Disease Surveillance & Response, website: http://www.who.int/csr/sars/archive/2003-05-07a/en and http://www.who.int/csr/sars/country/en/Country2003-08-15.pdf. Summary table of SARS cases by country (1 November 2002 to 7 August 2003).
5. N. Lee, D. Hui, A. Wu, P. Chan, P. Cameron, G.M. Joynt, A. Ahuja, M.Y. Yung, C.B. Leung, K.F. To, S.F. Lui, C.C. Szeto, S. Chung, and J.J.Y. Sung N. Engl. J. Med. 348 2003 1986
6. K. Anand, J. Ziebuhr, P. Wadhwani, J.R. Mesturs, and R. Hilgenfeld Science 300 2003 1763
7. P.A. Rota, M.S. Oberste, W.A. Nix, R. Campagnoli, J.P. Icenogle, S. Penaranda, B. Bankamp, K. Maher, M.H. Chen, S. Tong, A. Tamin, L. Lowe, M. Frace, J.L. DeRisi, Q. Chen, D. Wang, D.D. Erdman, T.C.T. Peret, C. Burns, T.G. Ksiazek, P.E. Rollin, A. Sanchez, S. Liffick, B. Holloway, J. Limor, K. McCaustland, M. Olsen-Rasmussen, R. Fouchier, S. Gunther, A.D.H.E. Osterhaus, C. Drosten, M.A. Pallansch, L.J. Anderson, and W.J. Bellini Science 300 2003 1394
8. V. Thiel, K.A. Ivanov, A.A. Putics, T. Hertzig, B. Schelle, S. Bayer, B. Weiabrich, E.J. Snijder, H. Rabenau, H.W. Doerr, and J. Ziebuhr J. Gen. Virol. 84 2003 2305
9. H. Yang, M. Yang, Y. Ding, Y. Liu, Z. Lou, Z. Zhou, L. Sun, L. Mo, S. Ye, H. Pang, G.F. Gao, K. Anand, M. Bartlam, R. Hilgenfeld, and Z. Rao Proc. Natl. Acad. Sci. U.S.A. 100 2003 13190
10. K. Chou, D. Wei, and W. Zhong Biochem. Biophys. Res. Commun. 308 2003 148
11. C.Y. Wu, J.T. Jan, S.H. Ma, C.J. Kuo, H.F. Juan, Y.S.E. Cheng, H.H. Hsu, H.C. Huang, D. Wu, B. Ashraf, F.S. Liang, R.S. Liu, J.M. Fang, S.T. Chen, P.H. Liang, and C.H. Wong Proc. Natl. Acad. Sci. U.S.A. 101 2004 10012
12. R.Y. Kao, W.H.W. Tsui, T.S.W. Lee, J.A. Tanner, R.M. Watt, J.D. Huang, L.H. Hu, G.H. Chen, Z.W. Chen, L.Q. Zhang, T. He, K.H. Chan, H. Tse, A.P.C. To, L.W.Y. Ng, B.C.W. Wong, H.W. Tsoi, D. Yang, D.D. Ho, and K.Y. Yuen Chem. Biol. 11 2004 1293
13. U. Bacha, J. Barrila, A. Velazquez-Campoy, S.A. Leavitt, and E. Freire Biochemistry 43 2004 4906
14. R.P. Jain, H.I. Pettersson, J.M. Zhang, K.D. Aull, P.D. Fortin, C. Huitema, L.D. Eltis, J.C. Parrish, M.N.G. James, D.S. Wishart, and J.C. Vederas J. Med. Chem. 47 2004 6113
15. L.R. Chen, Y.C. Wang, Y.W. Lin, S.Y. Chou, S.F. Chen, L.T. Liu, Y.T. Wu, K.B. Chih-Jung, T.S.S. Chen, and S.H. Juang Bioorg. Med. Chem. Lett. 15 2005 3058
16. J.E. Blanchard, N.H. Elowe, C. Huitema, P.D. Fortin, J.D. Cechetto, L.D. Eltis, and E.D. Brown Chem. Biol. 11 2004 1445
17. J.T.A. Hsu, C.J. Kuo, H.P. Hsieh, Y.C. Wang, K.K. Huang, C.P.C. Lin, P.F. Huang, X. Chen, and P.H. Liang FEBS Lett. 574 2004 116
18. L.L. Chen, C.S. Gui, X.M. Luo, Q.G. Yang, S. Gunther, E. Scandella, C. Drosten, D. Bai, X.C. He, B. Ludewig, J. Chen, H.B. Luo, Y.M. Yang, Y.F. Yang, J.P. Zou, V. Thiel, K. Chen, J.H. Shen, S. Xu, and H.L. Jiang J. Virol. 79 2005 7095
19. Z. Liu, C. Huang, K. Fan, P. Wei, H. Chen, S. Liu, J. Pei, L. Shi, B. Li, K. Yang, Y. Liu, and L. Lai J. Chem. Inf. Model. 45 2005 10
20. C.Y. Wu, K.Y. King, C.J. Kuo, J.M. Fang, Y.T. Wu, M.Y. Ho, C.L. Liao, J.J. Shie, P.H. Liang, and C.H. Wong Chem. Biol. 13 2006 4469
21. A.K. Ghosh, K. Xi, V. Grum-Tokars, X. Xu, K. Ratia, W. Fu, K.V. Houser, S.C. Baker, M.E. Johnson, and A.D. Mesecar Bioorg. Med. Chem. Lett. 17 2007 5876
22. J.J. Shie, J.M. Fang, T.H. Kuo, C.J. Kuo, P.H. Liang, H.J. Huang, W.B. Yang, C.H. Lin, J.L. Chen, Y.T. Wu, and C.H. Wong J. Med. Chem. 48 2005 4469
23. M.O. Sydnes, Y. Hayashi, V.K. Sharma, T. Hamada, U. Bacha, J. Barrila, E. Freire, and Y. Kiso Tetrahedron 62 2006 8601
24. U. Bacha, J. Barrila, B. Gabelli, Y. Kiso, L.M. Amzel, and E. Freire Chem. Biol. Drug Des. 72 2008 34
25. T. Regnier, D. Sharma, K. Hidaka, U. Bacha, E. Freire, Y. Hayashi, and Y. Kiso Bioorg. Med. Chem. Lett. 19 2009 2722
26. Q. Tian, N.K. Nayyar, S. Babu, L. Chen, J. Tao, S. Lee, A. Tibbetts, T. Moran, J. Liou, M. Guo, and T.P. Kennedy Tetrahedron Lett. 42 2001 6807
27. S.E. Webber, K. Okano, T.L. Little, S.H. Reich, Y. Xin, S.A. Fuhrman, D.A. Matthews, R.A. Love, T.F. Hendrickson, A.K. Patick, J.W. Meador III, R.A. Ferre, E.L. Brown, C.E. Ford, S.L. Binford, and S.T. Worland J. Med. Chem. 41 1998 2786
28. K. Akaji, H. Konno, M. Onozuka, A. Makino, H. Saito, and K. Nosaka Bioorg. Med. Chem. 16 2008 9400
29. K. Akaji, H. Konno, H. Mitsui, K. Teruya, Y. Shimamoto, Y. Hattori, T. Ozaki, M. Kusunoki, and A. Sanjoh J. Med. Chem. 54 2011 7962
30. J. Barrila, U. Bacha, and E. Freire Biochemistry 45 2006 14908
31. H. Yang, W. Xie, X. Xue, K. Yang, J. Ma, W. Liang, Q. Zhao, Z. Zhou, D. Pei, J. Ziebuhr, R. Hilgenfeld, K.Y. Yuen, L. Wong, G. Gao, S. Chen, Z. Chen, D. Ma, M. Bartlam, and Z. Rao PLoS Biol. 3 2005 1742