Chemical synthesis, biological evaluation and structure-activity relationship analysis of azaisoindolinones, a novel class of direct enoyl-ACP reductase inhibitors as potential antimycobacterial agents

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 21, 2011, Pages 6225-6232

  Deraeve, Céline ^a   Dorobantu, Ioana Miruna ^a   Rebbah, Farah ^a   Le Quéméner, Frédéric ^a   Constant, Patricia ^c   Quémard, Annaïk ^b   Bernardes Génisson, Vania ^a   Bernadou, Jean ^a   Pratviel, Geneviève ^a  

^a LCC LABORATOIRE DE CHIMIE DE COORDINATION   (France)

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

^c UNIVERSITÉ PAUL SABATIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 DODECYLOXY 1 PHENYL 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 HYDROXY 1 [3 (OCTADECYLOXY)PHENYL] 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 HYDROXY 1 [3 (OCTADECYLSULFANYL)PHENYL] 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 HYDROXY 1 [3 (OCTYLOXY)PHENYL] 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 HYDROXYL 1 TETRADECYL 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 [2 (DODECYLOXY)PHENYL] 1 HYDROXY 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 [3 (DODECYLAMINO)PHENYL] 1 HYDRO 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 [3 (DODECYLLSULFANYL)PHENYL] 1 HYDROXY 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 [3 (DODECYLOXY)PHENYL] 1 METHOXY 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 1 [4 (DODECYLOXY)PHENYL] 1 HYDROXY 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 2 (DODECYL) 1 HYDROXY 1 PHENYL 1,2 DIHYDRO 3H PYRROLO[3,4 C]PYRIDIN 3 ONE; 2 DODECYL 1H PYRROLO[3,4 C]PYRIDIN 1,3 ONE; ANTIMYCOBACTERIAL AGENT; AZAISOINDOLINONE; CIPROFLOXACIN; ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADH); ISONIAZID; OXINDOLE; PHENYL GROUP; TERT BUTYL N DODECYL 3[(1 HYDROXY 3 OXO 2,3 DIHYDRO 1H PYRROLO [3,4 C]PYRIDIN 1 YL)]PHENYLCARBAMATE; TRICLOSAN; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; CHIRAL CHROMATOGRAPHY; CHIRALITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; ENANTIOMER; ENZYME ACTIVITY; ENZYME INHIBITION; GROWTH INHIBITION; LIPOPHILICITY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION; SUPERCRITICAL FLUID CHROMATOGRAPHY;

MYCOBACTERIUM TUBERCULOSIS;

EID: 80054883656     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.09.017     Document Type: Article

References (20)

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: Berlin, 1988.
2. Zhang, Y.; Heym, B.; Allen, B.; Young, D.; Cole, S. Nature 1992, 358, 591.
3. Johnsson, K.; Schultz, P. G. J. Am. Chem. Soc. 1994, 116, 7425.
4. Johnsson, K.; King, D. S.; Schultz, P. G. J. Am. Chem. Soc. 1995, 117, 5009.
5. Quémard, A.; Lacave, C.; Lanéelle, G. Antimicrob. Agents Chemother. 1991, 35, 1035.
6. Saint-Joanis, B.; Souchon, H.; Wilming, M.; Johnsson, K.; Alzari, P.; Cole, S. T. Biochem. J. 1999, 338, 753.
7. Yu, S.; Girotto, S.; Lee, C.; Magliozzo, R. S. J. Biol. Chem. 2003, 278, 14769.
8. Heym, B.; Alzari, P.; Honoré, N. Mol. Microbiol. 1995, 15, 235.
9. Ramaswamy, S. V.; Reich, R.; Dou, S.-J.; Jasperse, L.; Pan, X.; Wenger, A.; Quitugua, T.; Graviss, E. A. Antimicrob. Agents Chemother. 2003, 47, 1241.
10. Delaine, T.; Bernardes-Génisson, V.; Quémard, A.; Constant, P.; Meunier, B.; Bernadou, J. Eur. J. Med. Chem. 2010, 45, 4554.
11. Bernadou, J.; Bernardes-Génisson, V.; Delaine, T.; Quémard, A. Nouveaux dérivés anti-infectieux, leur procédé de préparation, compositions pharmaceutiques les contenant et leurs utilisation en thérapeutique. PCT WO2009/101345.
12. Broussy, S.; Bernardes-Génisson, V.; Quémard, A.; Meunier, B.; Bernadou, J. J. Org. Chem. 2005, 70, 10502.
13. Delaine, T.; Bernardes-Génisson, V.; Quémard, A.; Constant, P.; Meunier, B.; Bernadou J. Unpublished.
14. Nguyen, M.; Quémard, A.; Broussy, S.; Bernadou, J.; Meunier, B. Antimicrob. Agents Chemother. 2002, 46, 2137.
15. Stigliani, J. L.; Arnaud, P.; Delaine, T.; Bernardes-Génisson, V.; Meunier, B.; Bernadou, J. J. Mol. Graph. Model. 2008, 27, 536.
16. Broussy, S.; Bernardes-Génisson, V.; Gornitzka, H.; Bernadou, J.; Meunier, B. Org. Biomol. Chem. 2005, 3, 666.
17. Quémard, A.; Sacchettini, J. C.; Dessen, A.; Vilcheze, C.; Bittman, R.; Jacobs, W. R., Jr.; Blanchard, J. S. Biochemistry 1995, 34, 8235.
18. Goldman, P.; Vagelos, P. R. J. Biol. Chem. 1961, 236, 2620.
19. 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.
20. Quémard, A.; Blanchard, J. S.; Jacobs, W. R., Jr.; Sacchettini, J. C. Science 1995, 267, 1638.