The first chemical synthesis of the core structure of the benzoylhydrazine-NAD adduct, a competitive inhibitor of the Mycobacterium tuberculosis enoyl reductase

Journal of Organic Chemistry

Volumn 70, Issue 25, 2005, Pages 10502-10510

  Broussy, Sylvain ^a   Bernardes Génisson, Vania ^a   Quémard, Annaïk ^b   Meunier, Bernard ^a   Bernadou, Jean ^a  

^a CNRS   (France)

^b INSTITUT DE PHARMACOLOGIE ET DE BIOLOGIE STRUCTURALE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITION; METABOLITES; OXIDATION; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

ADDUCTS; CORE STRUCTURE; CYCLIC DERIVATIVES; NUCLEUS;

ENZYMES;

1,2 DIHYDROPYRIDINE DERIVATIVE; 1,4 DIHYDROPYRIDINE DERIVATIVE; 4 BENZOYL 1,4 DIHYDRONICOTINAMIDE RIBONUCLEOSIDE; BACTERIAL ENZYME; BENZOHYDRAZIDE; DIHYDROPYRIDINE DERIVATIVE; ENOYL REDUCTASE; HYDRAZINE DERIVATIVE; ISONIAZID; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; PYRIDINIUM DERIVATIVE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYCLIZATION; DRUG TARGETING; ENZYME INHIBITION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ANTITUBERCULAR AGENTS; BINDING, COMPETITIVE; CYCLIZATION; ENZYME INHIBITORS; HYDRAZINES; MYCOBACTERIUM TUBERCULOSIS; NAD; OXIDATION-REDUCTION; OXIDOREDUCTASES;

EID: 28744445549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051901z     Document Type: Article

References (50)

1. Bartmann, K.; Iwainski, H.; Kleeberg, H. H.; Mison, P.; Offe, H. H.; Otten, H.; Tettenborn, D.; Trnka, L. In Antituberculosis Drugs; Bartmann, K., Ed.; Springer-Verlag: Berlin, 1985.
2. Blanchard, J. S. Annu. Rev. Biochem. 1996, 65, 215-239.
3. Sinha, B. K. J. Biol. Chem. 1983, 258, 796-801.
4. Zhang, Y.; Heym, B.; Allen, B.; Young, D.; Cole, S. Nature 1992, 358, 591-593.
5. Johnsson, K.; Schultz, P. G. J. Am. Chem. Soc. 1994, 116, 7425-7426.
6. Johnsson, K.; King, D. S.; Schultz, P. G. J. Am. Chem. Soc. 1995, 117, 5009-5010.
7. Nguyen, M.; Claparols, C.; Bernadou, J.; Meunier, B. C. R. Acad. Sci. 2001, 5, 1-6.
8. Rozwarski, D. A.; Grant, G. A.; Barton, D. H. R.; Jacobs, W. R., Jr.; Sacchettini, J. C. Science 1998, 279, 98-102.
9. Wilming, M.; Johnsson, K. Angew. Chem., Int. Ed. 1999, 38, 2588-2590.
10. Nguyen, M.; Claparols, C.; Bernadou, J.; Meunier, B. ChemBioChem 2001, 2, 877-883.
11. Ducasse-Cabanot, S.; Cohen-Gonsaud, M.; Marrakchi, H.; Nguyen, M.; Zerbib, D.; Bernadou, J.; Daffé, M.; Labesse, G.; Quémard, A. Antimicrob. Agents Chemother. 2004, 48, 242-249.
12. Banerjee, A.; Dubnau, E.; Quémard, A.; Balasubramanian, V.; Sun Um, K.; Wilson, T.; Collins, D.; de Lisle, G.; Jacobs, W. R., Jr. Science 1994, 263, 227-230.
13. Quémard, A.; Dessen, A.; Sugantino, M.; Jacobs, W. R., Jr., Sacchetini, J. C.; Blanchard, J. S. J. Am. Chem. Soc. 1996, 118, 1561-1562.
14. Takayama, K.; Wang, L.; David, H. L. Antimicrob. Agents Chemother. 1972, 2, 29-35.
15. Quémard, A.; Lacave, C.; Lanéelle, G. Antimicrob. Agents Chemother. 1991, 35, 1035-1039.
16. Rawat, R.; Whitty, A.; Tonge, P. J. PNAS 2003, 100, 13881-13886.
17. Broussy, S.; Coppel, Y.; Nguyen, M.; Bernadou, J.; Meunier, B. Chem. Eur. J. 2003, 9, 2034-2038.
18. Broussy, S.; Bernardes-Génisson, V.; Coppel, Y.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 670-673.
19. Ramaswamy, S. V.; Reich, R.; Dou, S.-J.; Jasperse, L.; Pan, X.; Wanger, A.; Quitugua, T.; Graviss, E. A. Antimicrob. Agents Chemother. 2003, 1241-1250.
20. Heym, B.; Alzari, P. M.; Honoré N.; Cole, S. T.; Mol. Microbiol 1995, 15, 235-245.
21. Morris, S.; Bai, G. H.; Suffys, P.; Portillo-Gomez, L.; Fairchok, M.; Rouse, D. J. Inf. Dis. 1995, 171, 954-960.
22. Pretorius, G. S.; van Helden, P. D.; Sirgel, F.; Eisenach, K. D.; Victor, T. C. Antimicrob. Agents Chemother. 1995, 39, 2276-2281.
23. Rouse, D. A.; Li, Z.; Bai, G. H.; Morris, S. L. Antimicrob. Agents Chemother. 1995, 39, 2472-2477.
24. Broussy, S.; Bernardes-Génisson, V.; Gornitzka, H.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 666-669.
25. Wibaut, J. P.; Heeringa, L. G. Red. Trav. Chim. Pays-Bas Belg. 1955, 74, 1003-1020.
26. Karig, G.; Spencer, J. A.; Gallagher, T. Org. Lett. 2001, 3, 835-838.
27. Eisner, U.; Kuthan, J. Chem. Rev. 1972, 1.
28. Hentall, P. L.; Flowers, N.; Bugg, T. D. H. Chem. Commun. 2001, 2098-2099.
29. Wong, C. H.; Whitesides, G. M. J. Am. Chem. Soc. 1981, 103, 4890.
30. Mauzerall, D.; Westheimer, F. H. J. Am. Chem. Soc. 1955, 70, 2261.
31. Carelli, V.; Liberatore, F.; Scipione, L.; Musio, R.; Sciacovelli, O. Tetrahedron Lett. 2000, 41, 1235-1240.
32. Lo, H. C.; Buriez, O.; Kerr, J. B.; Fish, R. H. Angew. Chem., Int. Ed. 1999, 38, 1429-1432.
33. Konno, H.; Sakamoto, K.; Ishitani, O. Angew. Chem., Int. Ed. 2000, 39, 4061-4063.
34. Steckhan, E.; Herrmann, S.; Ruppert, R.; Dietz, E.; Frede, M.; Spika, E. Organometallics 1991, 10, 1568-1577.
35. Büchi, G.; Coffen, D. L.; Kocsis, K.; Sonnet, P. E.; Ziegler, F. E. J. Am. Chem. Soc. 1966, 88, 3099-3109 and references therein.
36. Nutaitis, C. F. J. Chem. Educ. 1989, 66, 673-675.
37. Lee, J.; Churchil, H.; Choi, W.-B.; Lynch, J. E.; Roberts, F. E.; Volante, R. P.; Reider, P. J. Chem. Commun. 1999, 729-730.
38. Mickhailopulo, I. A.; Pricota, T. I.; Timoshchuk, V. A.; Akhrem, A. A. Synthesis 1981, 388-389.
39. Adapted from Ellerwik, U.; Magnusson, G. Tetrahedron Lett. 1997, 38, 1627-1628.
40. Quémard, A.; Sacchettini, J. C.; Dessen, A.; Vilcheze, C.; Bittman, R.; Jacobs, W. R., Jr.; Blanchard, J. S. Biochemistry 1995, 34, 8235-8241.
41. Lei, B.; Wei, C.-J.; Tu, S.-C. J. Biol. Chem. 2000, 275, 2520-2526.
42. Nguyen, M.; Quémard, A.; Broussy, S.; Bernadou, J.; Meunier, B. Antimicrob. Agents Chemother. 2002, 46, 2137-2144.
43. Velezheva, V. S.; Brennan, P. J.; Marshakov, V. Y.; Gusev, D. V.; Lisichkina, I. N.; Pergudov, A. S.; Tchernousova, L. N.; Smirnova, T. G.; Andreevskaya, S. N.; Medvedev, A. E. J. Med. Chem. 2004, 47, 3455-3461.
44. Pasqualoto, K. F. M.; Ferreira, E. I.; Santos-Filho, O. A.; Hopfinger, A. J. J. Med. Chem. 2004, 47, 3755-3764.
45. Sacchettini, J. InhA crystals and three-dimensional structure. United States Patent 5,882,878, March 16, 1999.
46. Staveski, M. M.; Sneddon, S. F.; Yee, C.; Janjigian, A. (Applicant Genzyme Corp.). InhA inhibitors and methods of use thereof. PCT/US01/40045, WO 01/56974 A2, August 9, 2001.
47. Yatvin, M. B.; Pederson, R. L. (Applicant Enzrel, Inc.). Anti-mycobacterial compounds. PCT/US01/21640, WO 02/04478 A1, January 17, 2002.
48. Quémard, A.; Daffé, M.; Ducasse, S.; Marrakchi, H.; Labesse, G.; Cohen-Gonsaud, M.; Doughet, D. (Applicants CNRS/University Montpellier 1/INSERM). Use of the protein MabA (FABG1) of Mycobacterium tuberculosis for designing and screening antibiotics. FP 02 04018, March 29, 2002; WO 03/082911, October 9, 2003.
49. Andries, K.; Verhasselt, P.; Guillemont, J. et al. Science 2005, 307, 223-227.
50. Robins, M. J.; Hatfield, P. W. Can. J. Chem. 1982, 60, 547-553.