Rational design of 5-phenyl-3-isoxazolecarboxylic acid ethyl esters as growth inhibitors of Mycobacterium tuberculosis. A potent and selective series for further drug development

Journal of Medicinal Chemistry

Volumn 53, Issue 2, 2010, Pages 678-688

  Lilienkampf, Annamaria ^a   Pieroni, Marco ^a   Wan, Baojie ^a   Wang, Yuehong ^a   Franzblau, Scott G ^a   Kozikowski, Alan P ^a  

^a UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 [3 [[(3 TRIFLUOROMETHYL)PHENYL]METHOXY]PHENYL] 3 ISOXAZOLECARBOXYLIC ACID ETHYL ESTER; 5 PHENYL 3 ISOXAZOLECARBOXYLIC ACID ETHYL ESTER; ISONIAZID; ISOXAZOLE DERIVATIVE; RIFAMPICIN; STREPTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL GROWTH; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; GROWTH INHIBITION; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANCE; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS; VERO CELL;

ANIMALS; ANTITUBERCULAR AGENTS; CERCOPITHECUS AETHIOPS; DRUG DESIGN; DRUG RESISTANCE, BACTERIAL; ESTERS; ISOXAZOLES; MYCOBACTERIUM TUBERCULOSIS; STRUCTURE-ACTIVITY RELATIONSHIP; VERO CELLS;

EID: 77249153741     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm901273n     Document Type: Article

References (26)

1. World Health Organization. Global Tuberculosis Control: Surveillance, Planning, and Financing. WHO Report 2008; WHO Press: Geneva, Switzerland, 2008.
2. (a) Boshoff, H. I. M.; Barry, C. E., III Tuberculosis: metabolism and respiration in the absence of growth. Nat. Rev. Microbiol. 2005, 3, 70-80.
3. (b)Wayne, L. G.; Sohaskey, C. D. Nonreplicating persistence of Mycobacteriumtuberculosis. Annu. Rev. Microbiol. 2001, 55, 139-163.
4. World Health Organization. Anti-Tuberculosis Drug Resistance in the World: Fourth Global Report. WHO Press: Geneva, Switzerland, 2008.
5. World Health Organization. Guidelines for the Programmatic Management of Drug-Resistant Tuberculosis. Emergency Update 2008; WHO Press: Geneva, Switzerland, 2008.
6. (a) Spigelman, M. K. New tuberculosis therapeutics: a growing pipeline. J. Infect. Dis. 2007, 196, S28-S34.
7. (b) Janin, Y. L. Antituberculosis drugs: ten years of research. Bioorg. Med. Chem. 2007, 15, 2479-2513.
8. Andries, K.; Verhasselt, P.; Guillemont, J.; Goehlmann, H. W. H.; Neefs, J.-M.; Winkler, H.; Van Gestel, J.; Timmerman, P.; Zhu, M.; Lee, E.; Williams, P.; de Chaffoy, D.; Huitric, E.; Hoffner, S.; Cambau, E.; Truffot-Pernot, C.; Lounis, N.; Jarlier, V. A diarylquinoline drug active on the ATP synthase of Mycobacterium tuberculosis. Science 2005, 307, 223-227.
9. (a) Stover, C. K.; Warrener, P.; Van Devanter, D. R.; Sherman, D. R.; Arain, T. M.; Langhorne, M. H.; Anderson, S. W.; Towell, J. A.; Yuan, Y.; McMurray, D. N.; Krelswirth, B. N.; Barry, C. E.; Baker, W. R. A small-molecule nitroimidazopyran drug candidate for the treatment of tuberculosis. Nature 2000, 405, 962-966.
10. (b) Lenaerts, A. J.; Gruppo, V.; Marietta, K. S.; Johnson, C. M.; Driscoll, D. K.; Tompkins, N. M.; Rose, J. D.; Reynolds, R. C.; Orme, I. M. Preclinical testing of the nitroimidazopyran PA-824 for activity against Mycobacterium tuberculosis in a series of in vitro and in vivo models. Antimicrob. Agents Chemother. 2005, 49, 2294-2301.
11. Matsumoto, M.; Hashizume, H.; Tomishige, T.; Kawasaki, M.; Tsubouchi, H.; Sasaki, H.; Shimokawa, Y.; Komatsu, M. OPC-67683, a nitro-dihydro- imidazooxazole derivative with promising action against tuberculosis in vitro and in mice. PLoS Med. 2006, 3, 2131-2144.
12. Rivers, E. C.; Mancera, R. L. New anti-tuberculosis drugs in clinical trials with novel mechanisms of action. Drug Discovery Today 2008, 13, 1090-1098.
13. Koul, A.; Dendouga, N.; Vergauwen, K.; Molenberghs, B.; Vranckx, L.; Willebrords, R.; Ristic, Z.; Lill, H.; Dorange, I.; Guillemont, J.; Bald, D.; Andries, K. Diarylquinolines target subunit c of mycobacterial ATP synthase. Nat. Chem. Biol. 2007, 3, 323-324.
14. Singh, R.; Manjunatha, U.; Boshoff, H. I. M.; Ha, Y. H.; Niyomrattanakit, P.; Ledwidge, R.; Dowd, C. S.; Lee, I. Y.; Kim, P.; Zhang, L.; Kang, S.; Keller, T. H.; Jiricek, J.; Barry, C. E., III. PA-824 kills nonreplicating mycobacterium tuberculosis by intracellular NO release. Science 2008, 322, 1392-1395.
15. (a) Jayaprakash, S.; Iso, Y.; Wan, B.; Franzblau, S. G.; Kozikowski, A. P. Design, synthesis, and SAR studies of mefloquine-based ligands as potential antituberculosis agents. ChemMedChem 2006, 1, 593-597.
16. (b) Mao, J.; Wang, Y.; Wan, B.; Kozikowski, A. P.; Franzblau, S. G. Design, synthesis, and pharmacological evaluation of mefloquine-based ligands as novel antituberculosis agents. Chem-MedChem 2007, 2, 1624-1630.
17. Mao, J.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. HTS, chemical hybridization, and drug design identify a chemically unique antituberculosis agent;coupling serendipity and rational approaches to drug discovery. ChemMedChem 2007, 2, 811-813.
18. Lilienkampf, A.; Mao, J.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. Structure-activity relationships for a series of quinoline-based compounds active against replicating and nonreplicating Mycobacterium tuberculosis. J. Med. Chem. 2009, 52, 2109-2118.
19. Mao, J.; Yuan, H.; Wang, Y.; Wan, B.; Pieroni, M.; Huang, Q.; van Breemen, R. B.; Kozikowski, A. P.; Franzblau, S. G. From serendipity to rational antituberculosis drug discovery of mefloquine-isoxazole carboxylic acid esters. J. Med. Chem. 2009, 52, 6966-6978.
20. Pieroni, M.; Lilienkampf, A.; Wan, B.; Wang, Y.; Franzblau, S. G.; Kozikowski, A. P. Synthesis, biological evaluation, and structure-activity relationships for 5-[(E)-2-arylethenyl]-3-isoxazolecarboxylic acid alkyl ester derivatives as valuable antitubercular chemotypes. J. Med. Chem. 2009, 52, 6287-6296.
21. (a) Rakesh; Sun, D.; Lee, R. B.; Tangallapally, R. P.; Lee, R. E. Synthesis, optimization and structure-activity relationships of 3,5-disubstituted isoxazolines as new anti-tuberculosis agents. Eur. J. Med. Chem. 2009, 44, 460-472.
22. (b) Tangallapally, R. P.; Sun, D.; Rakesh; Budha, N.; Lee, R. E. B.; Lenaerts, A. J. M.; Meibohm, B.; Lee, R. E. Discovery of novel isoxazolines as anti-tuberculosis agents. Bioorg. Med. Chem. Lett. 2007, 17, 6638-6642.
23. Xin, Z.; Liu, G.; Pei, Z.; Szczepankiewicz, B. G.; Serby, M. D.; Zhao, H. Preparation of Arylisoxazolecarboxylates as Protein-Tyrosine Phosphatase (PTP1B) Inhibitors. U.S. Pat. Appl. 2004214870 A1, 2004.
24. (a) Collins, L.; Franzblau, S. G. Microplate alamar 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.
25. (b) Falzari, K.; Zhu, Z.; Pan, D.; Liu, H.; Hongmanee, P.; Franzblau, S. G. In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 1997, 41, 1004-1009.
26. Cho, S. H.; Warit, S.; Wan, B.; Hwang, C. H.; Pauli, G. F.; Franzblau, S. G. Low-oxygen-recovery assay for high-throughput screening of compounds against nonreplicating Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 2007, 51, 1380-1385.