Synthesis and in vitro activity of 1,2,4-triazole-ciprofloxacin hybrids against drug-susceptible and drug-resistant bacteria

European Journal of Medicinal Chemistry

Volumn 60, Issue , 2013, Pages 128-134

  Plech, Tomasz ^a   Wujec, Monika ^a   Kosikowska, Urszula ^a   Malm, Anna ^a   Rajtar, Barbara ^a   Polz Dacewicz, Małgorzata ^a  

^a MEDICAL UNIVERSITY OF LUBLIN   (Poland)

Author keywords

Bactericidal effect; Fluoroquinolones; Mannich reaction; MRSA

Indexed keywords

1 CYCLOPROPYL 6 FLUORO 7 [4 [[3 (3 HYDROXYPHENYL) 4 (3 IODOPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [[3 (3 HYDROXYPHENYL) 4 (3 NITROPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [[4 (3 IODOPHENYL) 3 (N PROPYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [[4 (3 IODOPHENYL) 3 METHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1 CYCLOPROPYL 6 FLUORO 7 [4 [[4 (3 IODOPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 1,2,4 TRIAZOLE DERIVATIVE; 7 [4 [[3 (3 CHLOROPHENYL) 4 (2,4 DICHLOROPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (2,4 DIFLUOROPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (3 IODOPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (3,5 DICHLOROPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (4 IODOPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (4 METHOXYPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINONE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (N BUTYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 (N HEXYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 ETHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[3 (3 CHLOROPHENYL) 4 METHYL 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[4 (2,4 DICHLOROPHENYL) 3 (3 HYDROXYPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[4 (3,5 DICHLOROPHENYL) 3 (3 HYDROXYPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; 7 [4 [[4 (4 BROMOPHENYL) 3 (3 CHLOROPHENYL) 5 THIOXO 4,5 DIHYDRO 1H 1,2,4 TRIAZOL 1 YL]METHYL]PIPERAZIN 1 YL] 1 CYCLOPROPYL 6 FLUORO 4 OXO 1,4 DIHYDROQUINOLINE 3 CARBOXYLIC ACID; ANTIINFECTIVE AGENT; CIPROFLOXACIN; UNCLASSIFIED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ANTIBIOTIC SENSITIVITY; ARTICLE; BACILLUS CEREUS; BACTERICIDAL ACTIVITY; CELL DENSITY; CELL STRAIN HEK293; CYTOTOXICITY; DRUG SYNTHESIS; ESCHERICHIA COLI; HUMAN; HUMAN CELL; IN VITRO STUDY; LIPOPHILICITY; MANNICH REACTION; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MICROCOCCUS LUTEUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PROTEUS MIRABILIS; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS EPIDERMIDIS; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; CELLS, CULTURED; CIPROFLOXACIN; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG RESISTANCE, BACTERIAL; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HEK293 CELLS; HUMANS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 84871689627     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.11.040     Document Type: Article

References (30)

1. J.T. Cross Jr. Fluoroquinolones Semin. Pediatr. Infect. Dis. 12 2001 211 223
2. S. Emami, A. Shafiee, and A. Foroumadi Structural features of new quinolones and relationship to antibacterial activity against Gram-positive bacteria Mini Rev. Med. Chem. 6 2006 375 386
3. M. Berlanga, M.T. Montero, J. Hernandez-Borrell, and M. Vinas Influence of the cell wall on ciprofloxacin susceptibility in selected wild-type Gram-negative and Gram-positive bacteria Int. J. Antimicrob. Agents 23 2004 627 630
4. P.S. Charifson, A.L. Grillot, T.H. Grossman, J.D. Parsons, M. Badia, S. Bellon, D.D. Deininger, J.E. Drumm, C.H. Gross, A. LeTiran, Y.S. Liao, N. Mani, D.P. Nicolau, E. Perola, S. Ronkin, D. Shannon, L.L. Swenson, Q. Tang, P.R. Tessier, S.K. Tian, M. Trudeau, T.S. Wang, Y.Y. Wei, H. Zhang, and D. Stamos Novel dual-targeting benzimidazole urea inhibitors of DNA gyrase and topoisomerase IV possessing potent antibacterial activity: intelligent design and evolution through the judicious use of structure-guided design and structure-activity relationships J. Med. Chem. 51 2008 5243 5263
5. F. Alovero, X.-S. Pan, J. Morris, R. Manzo, and L. Fisher Engineering the specificity of antibacterial fluoroquinolones: benzenesulfonamide modifications at C-7 of ciprofloxacin change its primary target in Streptococcus pneumoniae from topoisomerase IV to gyrase Antimicrob. Agents Chemother. 44 2000 320 325
6. H. Nikaido, and D.G. Thanassi Penetration of lipophilic agents with multiple protonation sites into bacterial cells: tetracyclines and fluoroquinolones as examples Antimicrob. Agents Chemother. 37 1993 1393 1399
7. J.S. Chapman, and N.H. Georgopapadakou Routes of quinolone permeation in Escherichia coli Antimicrob. Agents Chemother. 32 1988 438 442
8. A.J.H. Marshall, and L.J.V. Piddock Interaction of divalent cations, quinolones and bacteria J. Antimicrob. Chemother. 34 1994 465 483
9. T.D. Gootz, and K.E. Brighty Fluoroquinolone antibacterials: SAR, mechanism of action, resistance, and clinical aspects Med. Res. Rev. 16 1996 433 486
10. L.L. Shen, L.A. Mitscher, P.N. Sharma, T.J. O'Donnell, D.W.T. Chu, C.S. Cooper, T. Rosen, and A.G. Pernet Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug-DNA binding model Biochemistry 28 1989 3886 3894
11. A. Foroumadi, S. Mansouri, Z. Kiani, and A. Rahmani Synthesis and in vitro antibacterial evaluation of N-[5-(5-nitro-2-thienyl)-1,3,4-thiadiazole-2- yl] piperazinyl quinolones Eur. J. Med. Chem. 38 2003 851 854
12. A. Foroumadi, F. Soltani, M.H. Moshafi, and R. Ashraf-Askari Synthesis and in vitro antibacterial activity of some N-(5-aryl-1,3,4-thiadiazole-2-yl) piperazinyl quinolone derivatives Il Farmaco 58 2003 1023 1028
13. A. Foroumadi, R. Ashraf-Askari, M.H. Moshafi, S. Emami, and A. Zeynali Synthesis and in vitro antibacterial activity of N-[5-(5-nitro-2-furyl)-1,3,4- thiadiazole-2-yl]piperazinyl quinolone derivatives Pharmazie 58 2003 432 433
14. A. Foroumadi, S. Mansouri, S. Emami, J. Mirzaei, M. Sorkhi, N. Saeid-Adeli, and A. Shafiee Synthesis and antibacterial activity of nitroaryl thiadiazole-levofloxacin hybrids Arch. Pharm. Chem. Life Sci. 339 2006 621 624
15. A. Foroumadi, S. Emami, A. Hassanzadeh, M. Rajaee, K. Sokhanvar, M.H. Moshafi, and A. Shafiee Synthesis and antibacterial activity of N-(5-benzylthio-1,3,4-thiadiazol-2-yl) and N-(5-benzylsulfonyl-1,3,4-thiadiazol- 2-yl)piperazinyl quinolone derivatives Bioorg. Med. Chem. Lett. 15 2005 4488 4492
16. 3 ciprofloxacin methylene and ethylene isatin derivatives Eur. J. Med. Chem. 46 2011 341 348
17. A. Foroumadi, S. Emami, M. Mehni, M.H. Moshafi, and A. Shafiee Synthesis and antibacterial activity of N-[2-(5-bromothiophen-2-yl)-2-oxoethyl] and N-[(2-5-bromothiophen-2-yl)-2-oximinoethyl]derivatives of piperazinyl quinolones Bioorg. Med. Chem. Lett. 15 2005 4536 4539
18. M.G. Rabbani, M.R. Islam, M. Ahmad, and A.M.L. Hossion Synthesis of some NH-Derivatives of ciprofloxacin as antibacterial and antifungal agents Bangladesh J. Pharmacol. 6 2011 8 13
19. R. Cormier, W.N. Burda, L. Harrington, J. Edlinger, K.M. Kodigepalli, J. Thomas, R. Kapolka, G. Roma, B.E. Anderson, E. Turos, and L.N. Shaw Studies on the antimicrobial properties of N-acylated ciprofloxacins Bioorg. Med. Chem. Lett. 22 2012 6513 6520
20. J.C. McPherson III, R. Runner, T.B. Buxton, J.F. Hartmann, D. Farcasiu, I. Bereczki, E. Roth, S. Tollas, E. Ostorházi, F. Rozgonyi, and P. Herczegh Synthesis of osteotropic hydroxybisphosphonate derivatives of fluoroquinolone antibacterials Eur. J. Med. Chem. 47 2012 615 618
21. S. Wang, X.-D. Jia, M.-L. Liu, Y. Lu, and H.-Y. Guo Synthesis, antimycobacterial and antibacterial activity of ciprofloxacin derivatives containing a N-substituted benzyl moiety Bioorg. Med. Chem. Lett. 22 2012 5971 5975
22. A. Foroumadi, S. Ghodsi, S. Emami, S. Najjari, N. Samadi, M.H. Faramarzi, L. Beikmohammadi, F.H. Shirazi, and A. Shafiee Synthesis and antibacterial activity of new fluoroquinolones containing a substituted N-(phenethyl) piperazine moiety Bioorg. Med. Chem. Lett. 16 2006 3499 3503
23. T. Plech, M. Wujec, A. Siwek, U. Kosikowska, and A. Malm Synthesis and antimicrobial activity of thiosemicarbazides, s-triazoles and their Mannich bases bearing 3-chlorophenyl moiety Eur. J. Med. Chem. 46 2011 241 248
24. T.D. Tran, T.H. Do, N.C. Tran, T.D. Ngo, T.N.P. Huynh, C.D. Tran, and K.M. Thai Synthesis and anti methicillin resistant Staphylococcus aureus activity of substituted chalcones alone and in combination with non-beta-lactam antibiotics Bioorg. Med. Chem. Lett. 22 2012 4555 4560
25. T. Welte, and M.W. Pletz Antimicrobial treatment of nosocomial methicillin-resistant Staphylococcus aureus (MRSA) pneumonia: current and future options Int. J. Antimicrob. Agents 36 2010 391 400
26. G.A. Pankey, and L.D. Sabath Clinical relevance of bacteriostatic versus bactericidal mechanisms of action in the treatment of Gram-positive bacterial infections Clin. Infect. Dis. 38 2004 864 870
27. F. Kautzky, A. Hartinger, L.D. Köhler, and H.J. Vogt In vitro cytotoxicity of antimicrobial agents to human keratinocytes J. Eur. Acad. Dermatol. Venereol. 6 1996 159 166
28. M.J. Nieto, F.L. Alovero, R.H. Manzo, and M.R. Mazzieri Benzenesulfonamide analogs of fluoroquinolones. Antibacterial activity and QSAR studies Eur. J. Med. Chem. 40 2005 361 369
29. H. Nikaido Antibiotic resistance caused by Gram-negative multidrug efflux pump Clin. Infect. Dis. 27 1998 23 41
30. T. Takenouchi, and E. Munekata Amyloid beta-peptide-induced inhibition of MTT reduction in PC12h and C1300 neuroblastoma cells: effect of nitroprusside Peptides 19 1998 365 372