New fluorine-containing hydrazones active against MDR-tuberculosis

European Journal of Medicinal Chemistry

Volumn 46, Issue 10, 2011, Pages 4937-4945

  Vavříková, Eva ^a   Polanc, Slovenko ^b   Kočevar, Marijan ^b   Horváti, Kata ^c   Bsze, Szilvia ^c   Stolaříková, Jiřina ^d   Vávrová, Kateřina ^a   Vinšová, Jarmila ^a  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b UNIVERSITY OF LJUBLJANA   (Slovenia)

^c EÖTVÖS LORÁND UNIVERSITY   (Hungary)

^d Zdravotniho ustavu se sidlem v Ostrave   (Czech Republic)

Author keywords

Antitubercular drug; Hydrazone; In vitro activity; Multidrug resistant tuberculosis; Tuberculosis

Indexed keywords

1 CYCLOPROPYL 6 FLUORO 4 OXO 7 {4 [3 (FLUOROBENZOYLHYDRAZONO)METHYL]PIPERAZIN 1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 {4 [3 (TRIFLUOROMETHYLBENZOYL)HYDRAZONOMETHYL]PIPERAZIN-1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 4 OXO 7 {4 [4 (TRIFLUORMETHYLBENZOYL)]HYDRAZONOMETHYL]PIPERAZIN 1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 ETHYL 6 FLUORO 4 OXO 7 {4 [3 (FLUOROBENZOYL)HYDRAZONOMETHYL]PIPERAZIN 1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 ETHYL 6 FLUORO 4 OXO 7 {4 [4 (FLUOROBENZOYL)HYDRAZONOMETHYL]PIPERAZIN 1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 ETHYL 6 FLUORO 4 OXO 7 {4 [4 (TRIFLUOROMETHYLBENZOYL)HYDRAZONOMETHYL]PIPERAZIN 1 YL} 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 2 HYDROXY 4 [(3 TRIFLUOROMETHYLBENZOYL)HYDRAZONOMETHYLAMINO]BENZOIC ACID; 2 HYDROXY 4 [(4 TRIFLUOROMETHYLBENZOYL)HYDRAZONOMETHYLAMINO]BENZOIC ACID; 4 [(2 FLUOROBENZOYL)HYDRAZONOMETHYLAMINO] 2 HYDROXYBENZOIC ACID; 4 [(3 FLUOROBENZOYL)HYDRAZONOMETHYLAMINO] 2 HYDROXYBENZOIC ACID; 4 [(4 FLUOROBENZOYL)HYDRAZONOMETHYLAMINO] 2 HYDROXYBENZOIC ACID; CIPROFLOXACIN; FLUORINE; FORMYLCIPROFLOXACIN; HYDRAZONE DERIVATIVE; N {2 [4 (TRIFLUOROMETHYL)BENZOYL]HYDRAZONOMETHYL}PYRAZINE 2 CARBOXAMIDE; N {[2 ( FLUOROBENZOYL)HYDRAZINYL]METHYLENE}PYRAZINE 2 CARBOXAMIDE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ANTIBACTERIAL ACTIVITY; AQUEOUS SOLUTION; ARTICLE; CLINICAL ASSESSMENT TOOL; CONTROLLED STUDY; CYTOTOXICITY; DRUG DECOMPOSITION; DRUG SCREENING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MULTIDRUG RESISTANT TUBERCULOSIS; MYCOBACTERIUM KANSASII; MYCOBACTERIUM TUBERCULOSIS; PH; SELECTIVITY INDEX;

ANIMALS; ANTITUBERCULAR AGENTS; CELL LINE; FLUORINE; HUMANS; HYDRAZONES; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM; MYCOBACTERIUM KANSASII; PLASMA; RATS; TUBERCULOSIS, MULTIDRUG-RESISTANT;

EID: 80053202171     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.07.052     Document Type: Article

References (32)

1. Global tuberculosis control: a short update to the 2010 report. http://whqlibdoc.who.int/publications/2010/9789241564069-eng.pdf
2. The Stop TB Strategy, WHO. http://whqlibdoc.who.int/hq/2006/WHO-HTM-STB- 2006.368-eng.pdf
3. J. Vinšová, and M. Krátký S. Ngy, Z. K'ung, Drug-Resistant Tuberculosis: Causes, Diagnosis and Treatments 2009 Nova Publishers New York (chapter 2)
4. D. Sriram, P. Yogeeswari, and R.V. Devakaram Synthesis, in vitro and in vivo antimycobacterial activities of diclofenac acid hydrazones and amides Bioorg. Med. Chem. 14 2006 3113 3118
5. M.F. Saraiva, M.V.N. de Souza, M.E. Tran Huu Dau, D.P. Araújo, G.S.G. de Carvalho, and M.V. de Almeida Synthesis and antitubercular evaluation of new fluoroquinolone derivatives coupled with carbohydrates Carbohydr. Res. 345 2010 761 767
6. K.K. Bedia, O. Elcin, U. Seda, K. Fatma, S. Nathaly, R. Sevim, and A. Dimoglo Synthesis and characterization of novel hydrazide-hydrazones and the study of their structure-antituberculosis activity Eur. J. Med. Chem. 41 2006 1253 1261
7. S. Eswaran, A.V. Adhikari, N.K. Pal, and I.H. Chowdhury Design and synthesis of some new quinoline-3-carbohydrazone derivatives as potential antimycobacterial agents Bioorg. Med. Chem. Lett. 20 2010 1040 1044
8. J. Vinšová, A. Imramovský, J. Jampílek, J.F. Monreal, and M. Doležal Recent advances on isoniazid derivatives Anti-Infective Agents Med. Chem. 7 2008 12 31
9. A. Nayyar, A. Malde, E. Coutinho, and R. Jain Synthesis, anti-tuberculosis activity, and 3D-QSAR study of ring-substituted-2/4- quinolinecarbaldehyde derivatives Bioorg. Med. Chem. 14 2006 7302 7310 (Pubitemid 44403104)
10. E. Pelttari, E. Karhumaki, and J. Langshaw Carbohydrazones of substituted salicylaldehydes as potential lead compounds for the development of narrow-spectrum antimicrobials Z. Naturforschung C-A J. Biosciences 62 2007 483 486 (Pubitemid 47403756)
11. A. Imramovský, S. Polanc, J. Vinšová, M. Kočevar, J. Jampílek, Z. Rečková, and J. Kaustová A new modification of anti-tubercular active molecules Bioorg. Med. Chem. 15 2007 2551 2559 (Pubitemid 46367712)
12. B. Košmrlj, B. Koklič, and S. Polanc Transformation of hydrazine derivatives. Ethoxymethylene hydrazones as powerful reagents in organic synthesis Acta Chim. Slov. 43 1996 153 162
13. M.A. Ali, and M.S. Yar Synthesis and antimycobacterial activity of novel 4-[5-(substituted phenyl)-1-phenyl-4,5-dihydro-1H-3-pyrazoyl]-2-methylphenol derivatives Med. Chem. Res. 15 2007 463 470
14. http://www.taacf.org/Process-text.htm
15. J. De Smet, K. Boussery, K. Colpaert, P. De Sutter, P. De Paepe, J. Decruyenaere, and J. Van Bocxlaer Pharmacokinetics of fluoroquinolones in critical care patients: a bio-analytical HPLC method for the simultaneous quantification of ofloxacin, ciprofloxacin and moxifloxacin an human plasma J. Chromatogr. B 877 2009 961 967
16. Z. Vybíralová, M. Nobilis, J. Zoulová, J. Květina, and P. Petr High-performance liquid chromatographic determination of ciprofloxacin in human plasma J. Pharm. Biomed. Anal. 37 2005 851 858 (Pubitemid 40614811)
17. H. Miyamoto, H. Ueda, T. Otsuka, S. Aki, H. Tamaoka, M. Tominaga, and K. Nakagawa Studies on antibacterial agents. III.: synthesis and antibacterial activities of substituted 1,4-dihydro-8-methyl-4-oxoquinoline-3-carboxylic acid Chem. Pharm. Bull. 38 1990 2472 2475 (Pubitemid 20357300)
18. L. Sula WHO co-operative studies on a simple culture technique for isolation of mycobacteria. 1. Preparation, lyophylization and reconstitution of a simple semi-synthetic concentrated liquid medium - culture technique - growth patternal or different mycobacteria Bull. World Health Organ. 29 1963 589
19. L. Sula, and T.K. Sundares WHO co-operative studies on a simple culture technique for isolation of mycobacteria. 2. Comparison of efficacy of lyophylized liquid medium with that of Lowenstein-Jensen (L-J) medium Bull. World Health Organ. 29 1963 607
20. J. Vinsova, K. Cermakova, A. Tomeckova, M. Ceckova, J. Jampilek, P. Cermak, J. Kunes, M. Dolezal, and F. Staud Synthesis and antimicrobial evaluation of new 2-substituted 5,7-di-tert-butylbenzoxazoles Bioorg. Med. Chem. 14 2006 5850 5865 (Pubitemid 44080590)
21. K.A. Jensen Zentralb. Bakteriol. Parasitenkd. Infektionskr Hyg. Abt. I Orig 125 1932 222
22. E. Löwenstein Zentralb. Bakteriol. Parasitenkd. Infektionskr Hyg. Abt. I Orig 120 1931 127
23. S. Jurcevic, A. Hills, G. Pasvol, R.N. Davidson, J. Ivanyi, and R.J. Wilkinson T cell responses to a mixture of Mycobacterium tuberculosis peptides with complementary HLA-DR binding profiles Clin. Exp. Immunol. 105 1996 416 421 (Pubitemid 26297884)
24. B.B. Knowles, D. Aden, U.S. Patent 4,393,133, 1983.
25. B.B. Knowles, C.C. Howe, and D.P. Aden Human hepatocellular carcinoma cell lines secrete the major plasma proteins and hepatitis B surface antigen Science 209 1980 497 499
26. J.L. Biedler, L. Helson, and B.A. Spengler Morphology and growth, tumorigenicity, and cytogenetics of human neuroblastoma cells in continuous culture Cancer Res. 33 1973 2643 2652
27. J.L. Biedler, S. Roffler-Tarlov, M. Schachner, and L.S. Freedman Multiple neurotransmitter synthesis by human neuroblastoma cell lines and clones Cancer Res. 38 1978 3751 3757 (Pubitemid 9045201)
28. T.F. Slater, B. Sawyer, and U. Sträuli Studies on succinate-tetrazolium reductase systems: III. Points of coupling of four different tetrazolium salts III. Points of coupling of four different tetrazolium salts Biochim. Biophys. Acta 77 1963 383 393
29. T.J. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays Immunol. Methods 65 1983 55 63
30. Y.B. Liu, D.A. Peterson, H. Kimura, and D.J. Schubert Mechanism of cellular 3-(4,5- dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction Neurochem. 69 1997 581 593 (Pubitemid 27327958)
31. F.P. Altman Tetrazolium salts and formazans Prog. Histochem. Cytochem. 9 1976 1 56
32. F. Denizot, and R. Lang Rapid colorimetric assay for cell growth and survival: modifications to the tetrazolium dye procedure giving improved sensitivity and reliability J. Immunol. Methods 89 1986 271 277 (Pubitemid 16080782)