Severe acute respiratory syndrome coronavirus papain-like novel protease inhibitors: Design, synthesis, protein-ligand X-ray structure and biological evaluation

Journal of Medicinal Chemistry

Volumn 53, Issue 13, 2010, Pages 4968-4979

  Ghosh, Arun K ^a   Takayama, Jun ^a   Rao, Kalapala Venkateswara ^a   Ratia, Kiira ^b   Chaudhuri, Rima ^b   Mulhearn, Debbie C ^b   Lee, Hyun ^b   Nichols, Daniel B ^c   Baliji, Surendranath ^c   Baker, Susan C ^c   Johnson, Michael E ^b   Mesecar, Andrew D ^b  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^c LOYOLA UNIVERSITY CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 [1 (1 NAPHTHYL)ETHYL] 4 [3,4 (METHYLENEDIOXY)BENZYLAMINO]CARBONYLPIPERIDINE; 1 [1 METHYL 1 (1 NAPHTHYL)ETHYL] 4 [3,4 (METHYLENEDIOXY)BENZYLAMINO]CARBONYLPIPERIDINE; 6577871; DOCKING PROTEIN; PAPAIN; PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIVIRAL ACTIVITY; ARTICLE; BINDING SITE; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME INHIBITION; HIGH THROUGHPUT SCREENING; IC 50; LIGAND BINDING; MOLECULAR MODEL; NONHUMAN; PROTEIN STRUCTURE; SARS CORONAVIRUS; SEVERE ACUTE RESPIRATORY SYNDROME; STRUCTURE ACTIVITY RELATION; VERO CELL; X RAY CRYSTALLOGRAPHY;

ANIMALS; ANTIVIRAL AGENTS; CERCOPITHECUS AETHIOPS; CRYSTALLOGRAPHY, X-RAY; CYSTEINE ENDOPEPTIDASES; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MASS SPECTROMETRY; MODELS, MOLECULAR; PIPERIDINES; SARS VIRUS; SEVERE ACUTE RESPIRATORY SYNDROME; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS; VIRAL PROTEINS; VIRUS REPLICATION;

EID: 77954330172     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1004489     Document Type: Article

References (27)

1. World Health Organization. Communicable Disease Surveillance & Response. http://www.who.int/csr/sars/archive/2003-05-07a/en and http://www.who.int/csr/sars/country/en/coutry2003-08-15.pdf.
2. Drosten, C.; Gunther, S.; Preiser, W.; van der Werf, S.; Brodt, H. R.; Becker, S.; Rabenau, H.; Panning, M.; Kolesnikova, L.; Fouchier, R. A.; Berger, A.; Burguiere, A. M.; Cinatl, J.; Eickmann, M.; Escriou, N.; Grywna, K.; Kramme, S.; Manuguerra, J. C.; Muller, S.; Rickerts, V.; Sturmer, M.; Vieth, S.; Klenk, H. D.; Osterhaus, A. D.; Schmitz, H.; Doerr, H. W. Identification of a novel coronavirus in patients with severe acute respiratory syndrome N. Engl. J. Med. 2003, 348, 1967-1976 (Pubitemid 36569985)
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.; Rota, P.; Fields, B.; DeRisi, J.; Yang, J. Y.; Cox, N.; Hughes, J. M.; LeDuc, J. W.; Bellini, W. J.; Anderson, L. J. A novel coronavirus associated with severe acute respiratory syndrome N. Engl. J. Med 2003, 348, 1953-1966 (Pubitemid 36569984)
4. Peiris, J. S.; Lai, S. T.; Poon, L. L.; Guan, Y.; Yam, L. Y. C.; Lim, W.; Nicholls, J.; Yee, W. K. S.; Yan, W. W.; Cheung, M. T.; Cheng, V. C.; Chan, K. H.; Tsang, D. N.; Yung, R. W. H.; Ng, T. K.; Yuen, K. Y. Coronavirus as a possible cause of severe acute respiratory syndrome Lancet 2003, 361, 1319-1325 (Pubitemid 36514862)
5. Li, W.; Shi, Z.; Yu, M.; Ren, W.; Smith, C.; Epstein, J. H.; Wang, H.; Crameri, G.; Hu, Z.; Zhang, H.; Zhang, J.; McEachern, J.; Field, H.; Daszak, P.; Eaton, B. T.; Zhang, S.; Wang, L. F. Bats are natural reservoirs of SARS-like coronaviruses Science 2005, 310, 676-679
6. Lau, S. K. P.; Woo, P. C. Y.; Li, K. S. M.; Huang, Y.; Tsoi, H.-W.; Wong, B. H. L.; Wong, S. S. Y.; Leung, S. Y.; Chan, K.-H.; Yuen, K.-Y. Severe acute respiratory syndrome coronavirus-like virus in Chinese horseshoe bats Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 14040-14045
7. He, J. F.; Peng, G.-W.; Min, J.; Yu, D.-W.; Liang, W.-J.; Zhang, S.-Y.; Xu, R.-H.; Zheng, H.-Y.; Wu, X.-W.; Xu, J.; Wang, Z.-H.; Fang, L.; Zhang, X.; Li, H.; Yan, X.-G.; Lu, J.-H.; Hu, Z.-H.; Huang, J.-C.; Wan, Z.-Y.; Hou, J.-L.; Lin, J.-Y.; Song, H.-D.; Wang, S.-Y.; Zhou, X.-J.; Zhang, G.-W.; Gu, B.-W.; Zheng, H.-J.; Zhang, X.-L.; He, M.; Zheng, K.; Wang, B.-F.; Fu, G.; Wang, X.-N.; Chen, S.-J.; Chen, Z.; Hao, P.; Tang, H.; Ren, S.-X.; Zhong, Y.; Guo, Z.-M.; Liu, Q.; Miao, Y.-G.; Kong, X.-Y.; He, W.-Z.; Li, Y.-X.; Wu, C.-I.; Zhao, G.-P.; Chiu, R. W. K.; Chim, S. S. C.; Tong, Y.-K.; Chan, P. K. S.; Tam, J. S.; Lo, Y. M. D. Molecular evolution of the SARS-coronavirus during the course of the SARS epidemic in China Science 2004, 303, 1666-1669
8. Baker, S. C. Coronaviruses: Molecular Biology. In Encyclopedia of Virology, 3 rd ed.; Mahy, B. W. J.; Van Regenmortel, M. H. V., Eds.; Academic Press: Amsterdam, 2008; Vol. 1, pp 554 - 562.
9. Ghosh, A. K.; Xi, K.; Johnson, M. E.; Baker, S. C.; Mesecar, A. D. Progress in anti-SARS coronavirus chemistry, biology and chemotherapy Annu. Rep. Med. Chem. 2006, 41, 183-196
10. Yang, H.; Bartlam, M.; Rao, Z. Drug design targeting the main protease, the Achilles heel of coronaviruses Curr. Pharm. Des. 2006, 12, 4573-4590
11. Ghosh, A. K.; Xi, K.; Grum-Tokars, V.; Xu, X.; Ratia, K.; Fu, W.; Houser, K. V.; Baker, S. C.; Johnson, M. E.; Mesecar, A. D. Structure-based design, synthesis, and biological evaluation of peptidomimetic SARS-CoV 3CLpro inhibitors Bioorg. Med. Chem. Lett. 2007, 17, 5876-5880
12. 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.; Vederas, J. C. Synthesis and evaluation of keto-glutamine analogues as potent inhibitors of severe acute respiratory syndrome 3CLpro J. Med. Chem. 2004, 47, 6113-6434
13. Vederas, J. C.; Jain, R. P. Structural variations in keto-glutamines for improved inhibition against hepatitis A virus 3C proteinase Bioorg. Med. Chem. Lett. 2004, 14, 3655
14. Ratia, K.; Pegan, S.; Takayama, J.; Sleeman, K.; Coughlin, M.; Chaudhuri, R.; Fu, W.; Prabhakar, B. S.; Johnson, M. E.; Baker, S. C.; Ghosh, A. K.; Mesecar, A. D. A noncovalent class of papain-like protease/deubiquitinase inhibitors blocks SARS virus replication Proc. Natl. Acad. Sci. U.S.A. 2008, 105, 16119-16124
15. Ghosh, A. K.; Takayama, J.; Aubin, Y.; Ratia, K.; Chaudhuri, R.; Baez, Y.; Sleeman, K.; Coughlin, M.; Nichols, D. B.; Mulhearn, D. C.; Prabhakar, B. S.; Baker, S. C.; Johnson, M. E.; Mesecar, A. D. Structure-based design, synthesis, and biological evaluation of a series of novel and reversible inhibitors for the severe acute respiratory syndrome-coronavirus papain-like protease J. Med. Chem. 2009, 52, 5228-5240
16. Devaraj, S. G.; Wang, N.; Chen, Z.; Chen, Z.; Tseng, M.; Barretto, N.; Lin, R.; Peters, C. J.; Tseng, C.-T. K.; Baker, S. C.; Li, K. Regulation of IRF-3-dependent innate immunity by the papain-like protease domain of the severe acute respiratory syndrome coronavirus J. Biol. Chem. 2007, 282, 32208-32221
17. Ratia, K.; Saikatendu, K. S.; Santarsiero, B. D.; Barretto, N.; Baker, S. C.; Stevens, R. C.; Mesecar, A. D. Severe acute respiratory syndrome coronavirus papain-like protease: structure of a viral deubiquitinating enzyme Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 5717-5722
18. Barretto, N.; Jukneliene, D.; Ratia, K.; Chen, Z.; Mesecar, A. D.; Baker, S. C. The papain-like protease of severe acute respiratory syndrome coronavirus has deubiquitinating activity J. Virol. 2005, 79, 15189-15198
19. Lindner, H. A.; Fotouhi-Ardakani, N.; Lytvyn, V.; Lachance, P.; Sulea, T.; Ménard, R. The papain-like protease from the severe acute respiratory syndrome coronavirus is a deubiquitinating enzyme J. Virol. 2005, 79, 15199-15208 (Pubitemid 43032302)
20. Sulea, T.; Lindner, H. A.; Purisima, E. O.; Ménard, R. Deubiquitination, a new function of the severe acute respiratory syndrome coronavirus papain-like protease? J. Virol. 2005, 79, 4550-4551 (Pubitemid 40388395)
21. Ziebuhr, J.; Schelle, B.; Karl, N.; Minskaia, E.; Bayer, S.; Siddell, S. G.; Gorbalenya, A. E.; Thiel, V. Human coronavirus 229E papain-like proteases have overlapping specificities but distinct functions in viral replication J. Virol. 2007, 81, 3922-3932
22. Oba, M.; Tanaka, M.; Takano, Y.; Suemune, H. Concise synthetic strategy toward cyclic αα-disubstituted α-amino acids bearing a δ-nitrogen atom: chiral 1-substituted 4-aminopiperidine-4-carboxylic acids Tetrahedron 2005, 61, 593-598
23. Gaspari, P.; Banerjee, T.; Malachowski, W. P.; Muller, A. J.; Prendergast, G. C.; DuHadaway, J.; Bennett, S.; Donovan, A. M. Structure-activity study of brassinin derivatives as indoleamine 2,3- dioxygenase inhibitors J. Med. Chem. 2006, 49, 684-692
24. Dolby, L. D.; Biere, H. The total synthesis of (±)- epidasycarpidone and (±)-epiuleine J. Org. Chem. 1970, 35, 3843-3845
25. Yang, Q.; Ney, J. E.; Wolfe, J. P. Palladium-catalyzed tandem N-arylation/carboamination reactions for the stereoselective synthesis of N -aryl-2-benzyl pyrrolidines Org. Lett. 2005, 7, 2575-2578
26. Tahtaoui, C.; Parrot, I.; Klotz, P.; Guillier, F.; Galzi, J.-L.; Hibert, M.; Ilien, B. Fluorescent pirenzepine derivatives as potential bitopic ligands of the human M1 muscarinic receptor J. Med. Chem. 2004, 47, 4300-4315
27. Matsuno, K.; Ichimura, M.; Nakajima, T.; Tahara, K.; Fujiwara, S.; Kase, H.; Ushiki, J.; Giese, N. A.; Pandey, A.; Scarborough, R. M.; Lokker, N. A.; Yu, J.-C.; Irie, J.; Tsukuda, E.; Ide, S.; Oda, S.; Nomoto, Y. Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. 1. Synthesis, structure-activity relationship, and biological effects of a new class of quinazoline derivatives J. Med. Chem. 2002, 45, 3057-3066