Pyrrolidine carboxamides as a novel class of inhibitors of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis

Journal of Medicinal Chemistry

Volumn 49, Issue 21, 2006, Pages 6308-6323

  He, Xin ^a   Alian, Akram ^a   Stroud, Robert ^a   Ortiz De Montellano, Paul R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ENOYL ACYL CARRIER PROTEIN REDUCTASE INHA; ENOYL ACYL CARRIER PROTEIN REDUCTASE INHIBITOR; N [(ANTHRACEN 9 YL)METHYL] 1 (BICYCLO[2.2.1]HEPTAN 2 YL) N METHYL 5 OXO PYRROLIDINE 3 CARBOXAMIDE; N [(ANTRHACEN 9 YL)METHYL] 1 CYCLOHEXYL N METHYL 5 OXOPYRROLIDINE 3 CARBOXAMIDE; N [(ANTRHACEN 9 YL)METHYL] 1 CYCLOOCTYL N METHYL 5 OXOPYRROLIDINE 3 CARBOXAMIDE; N [3 (BENZYLOXY)PHENYL] 1 CYCLOHEXYL 5 OXOPYRROLIDINE 3 CARBOXAMIDE; N [3 BROMO 5 (TRIFLUOROMETHYL)PHENYL] 1 CYCLOHEXYL 5 OXOPYRROLIDINE 3 CARBOXAMIDE; OXIDOREDUCTASE; PYRROLIDINE CARBOXAMIDE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CHIRAL CHROMATOGRAPHY; CRYSTAL STRUCTURE; DERIVATIZATION; DRUG BINDING; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIGH THROUGHPUT SCREENING; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; RACEMIC MIXTURE; STRUCTURE ANALYSIS;

AMIDES; ANTITUBERCULAR AGENTS; BINDING SITES; CRYSTALLOGRAPHY, X-RAY; ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADH); MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; PROTEIN BINDING; PYRROLIDINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33750111588     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060715y     Document Type: Article

References (36)

1. Tuberculosis, NIAID Fact Sheet http://www.niaid.nih.gov/factsheets/ tb.htm.
2. Global Alliance for TB Drug Development (www.tballiance.org).
3. WHO fact sheet http://www.who.int/mediacentre/factsheets/who104/ en/print.html.
4. Campbell, J. W.; Cronan, J. E., Jr. Bacterial fatty acid biosynthesis: Targets for antibacterial drug discovery. Annu. Rev. Microbiol. 2001, 55, 305-332.
5. Heath, R. J.; Rock, C. O. Fatty acid biosynthesis as a target for novel antibacterials. Curr. Opin. Invest. Drugs 2004, 5, 146-153.
6. White, S. W.; Zheng, J.; Zhang, Y. M.; Rock, C. O. The structural biology of type II fatty acid biosynthesis. Annu. Rev. Biochem. 2005, 74, 791-831.
7. Zhang, Y. M.; Lu, Y. J.; Rock, C. O. The reductase steps of the type II fatty acid synthase as antimicrobial targets. Lipids 2004, 39, 1055-1060.
8. Takayama, K.; Wang, C.; Besra, G. S. Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin. Microbiol. Rev. 2005, 18, 81-101.
9. Banerjee, A.; Dubnau, E.; Quemard, A.; Balasubramanian, V.; Um, K. S.; Wilson, T.; Collins, D.; de Lisle, G.; Jacobs, W. R., Jr. inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Science 1994, 263, 227-230.
10. Zhang, Y.; Heym, B.; Allen, B.; Young, D.; Cole, S. The catalase-peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis. Nature 1992, 358, 591-593.
11. Escalante, P.; Ramaswamy, S.; Sanabria, H.; Soini, H.; Pan, X.; Valiente-Castillo, O.; Musser, J. M. Genotypic characterization of drug-resistant Mycobacterium tuberculosis isolates from Peru. Tuber. Lung Dis. 1998, 79, 111-118.
12. Roujeinikova, A.; Sedelnikova, S.; de Boer, G. J.; Stuitje, A. R.; Slabas, A. R.; Rafferty, J. B.; Rice, D. W. Inhibitor binding studies on enoyl reductase reveal conformational changes related to substrate recognition. J. Biol. Chem. 1999, 274, 30811-30817.
13. Heath, R. J.; Yu, Y. T.; Shapiro, M. A.; Olson, E.; Rock, C. O. Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis. J. Biol. Chem. 1998, 273, 30316-30320.
14. Kuo, M. R.; Morbidoni, H. R.; Alland, D.; Sneddon, S. F.; Gourlie, B. B.; Staveski, M. M.; Leonard, M.; Gregory, J. S.; Janjigian, A. D.; Yee, C.; Musser, J. M.; Kreiswirth, B.; Iwamoto, H.; Perozzo, R.; Jacobs, W. R., Jr.; Sacchettini, J. C.; Fidock, D. A. Targeting tuberculosis and malaria through inhibition of enoyl reductase: Compound activity and structural data. J. Biol. Chem. 2003, 278, 20851-20859.
15. McGovern, S. L.; Caselli, E.; Grigorieff, N.; Shoichet, B. K. A common mechanism underlying promiscuous inhibitors from virtual and high-throughput screening. J. Med. Chem. 2002, 45, 1712-1722.
16. Ryan, A. J.; Gray, N. M.; Lowe, P. N.; Chung, C. W. Effect of detergent on "promiscuous" inhibitors. J. Med. Chem. 2003, 46, 3448-3451.
17. Brik, A.; Lin, Y. C.; Elder, J.; Wong, C. H. A quick diversity-oriented amide-forming reaction to optimize P-subsite residues of HIV protease inhibitors. Chem. Biol. 2002, 9, 891-896.
18. Lee, L. V.; Mitchell, M. L.; Huang, S. J.; Fokin, V. V.; Sharpless, K. B.; Wong, C. H. A potent and highly selective inhibitor of human alpha-1,3-fucosyltransferase via click chemistry. J. Am. Chem. Soc. 2003, 125, 9588-9589.
19. Wu, C. Y.; Chang, C. F.; Chen, J. S.; Wong, C. H.; Lin, C. H. Rapid diversity-oriented synthesis in microtiter plates for in situ screening: Discovery of potent and selective alpha-fucosidase inhibitors. Angew. Chem., Int. Ed. Engl. 2003, 42, 4661-4664.
20. He, X.; Lin, Z. Y.; Zhu, L. Y.; Fu, H. J. Synthesis and vasodilative activities of benzamide derivatives. Acta Pharm. Sin. 1998, 33, 666-674.
21. Kim, I. H.; Heirtzler, F. R.; Morisseau, C.; Nishi, K.; Tsai, H. J.; Hammock, B. D. Optimization of amide-based inhibitors of soluble epoxide hydrolase with improved water solubility. J. Med. Chem. 2005, 48, 3621-3629.
22. Ward, W. H.; Holdgate, G. A.; Rowsell, S.; McLean, E. G.; Pauptit, R. A.; Clayton, E.; Nichols, W. W.; Colls, J. G.; Minshull, C. A.; Jude, D. A.; Mistry, A.; Timms, D.; Camble, R.; Hales, N. J.; Britton, C. J.; Taylor, I. W. Kinetic and structural characteristics of the inhibition of enoyl (acyl carrier protein) reductase by triclosan. Biochemistry 1999, 38, 12514-12525.
23. Qiu, X.; Janson, C. A.; Court, R. I.; Smyth, M. G.; Payne, D. J.; Abdel-Meguid, S. S. Molecular basis for triclosan activity involves a flipping loop in the active site. Protein Sci. 1999, 8, 2529-2532.
24. Roujeinikova, A.; Levy, C. W.; Rowsell, S.; Sedelnikova, S.; Baker, P. J.; Minshull, C. A.; Mistry, A.; Colls, J. G.; Gamble, R.; Stuitje, A. R.; Slabas, A. R.; Rafferty, J. B.; Pauptit, R. A.; Viner, R.; Rice, D. W. Crystallographic analysis of triclosan bound to enoyl reductase. J. Mol. Biol. 1999, 294, 527-535.
25. Levy, C. W.; Roujeinikova, A.; Sedelnikova, S.; Baker, P. J.; Stuitje, A. R.; Slabas, A. R.; Rice, D. W.; Rafferty, J. B. Molecular basis of triclosan activity. Nature 1999, 398, 383-384.
26. Stewart, M. J.; Parikh, S.; Xiao, G.; Tonge, P. J.; Kisker, C. Structural basis and mechanism of enoyl reductase inhibition by triclosan. J. Mol. Biol. 1999, 290, 859-865.
27. Paytash, P. L.; Sparrow, E.; Gathe, J. C. The reaction of itaconic acid with primary amines. J. Am. Chem. Soc. 1950, 72, 1415-1416.
28. Collins, L.; Franzblau, S. G. Microplate alaniar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
29. Parikh, S.; Moynihan, D. P.; Xiao, G.; Tonge, P. J. Roles of tyrosine 158 and lysine 165 in the catalytic mechanism of InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis. Biochemistry 1999, 38, 13623-13634.
30. Quemard, A.; Sacchettini, J. C.; Dessen, A.; Vilcheze, C.; Bittman, R.; Jacobs, W. R., Jr.; Blanchard, J. S. Enzymatic characterization of the target for isoniazid in Mycobacterium tuberculosis. Biochemistry 1995, 34, 8235-8241.
31. Dessen, A.; Quemard, A.; Blanchard, J. S.; Jacobs, W. R., Jr.; Sacchettini, J. C. Crystal structure and function of the isoniazid target of Mycobacterium tuberculosis. Science 1995, 267, 1638-1641.
32. Holton, J.; Alber, T. Automated protein crystal structure determination using ELVES. Proc. Natl. Acad. Sci. U.S.A. 2004, 101, 1537-1542.
33. Otwinowski, Z.; Minor, W. Processing of X-ray diffraction data collected in oscillation mode. Methods Enzymol. 1997, 276, 307-325.
34. Brunger, A. T.; Adams, P. D.; Clore, G. M.; DeLano, W. L.; Gros, P.; Grosse-Kunstleve, R. W.; Jiang, J. S.; Kuszewski, J.; Nilges, M.; Pannu, N. S.; Read, R. J.; Rice, L. M.; Simonson, T.; Warren, G. L. Crystallography & NMR system: A new software suite for macromolecular structure determination. Acta Crystallogr. D Biol. Crystallogr. 1998, 54, 905-921.
35. Kleywegt, G. J.; Jones, T. A. Databases in protein crystallography. Acta Crystallogr. D Biol. Crystallogr. 1998, 54, 1119-1131.
36. Bogeso, K. P. Neuroleptic activity and dopamine-uptake inhibition in 1-piperazino-3-phenylindans. J. Med. Chem. 1983, 26, 935-947.