Synthesis, and antibacterial activity of novel 4,5-dihydro-1H-pyrazole derivatives as DNA gyrase inhibitors

Organic and Biomolecular Chemistry

Volumn 12, Issue 6, 2014, Pages 998-1008

  Liu, Jia Jia ^a   Sun, Juan ^a   Fang, Yun Bin ^a   Yang, Yong An ^a   Jiao, Rui Hua ^a   Zhu, Hai Liang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIA; BIOMATERIALS; ESCHERICHIA COLI;

ANTI-BACTERIAL ACTIVITY; ANTI-BACTERIAL AGENTS; BINDING CONFORMATIONS; DOCKING SIMULATIONS; INHIBITORY ACTIVITY; MINIMUM INHIBITORY CONCENTRATION; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS;

DNA;

1-(5-(3,5-DICHLORO-2-(2,6-DINITRO-4-(TRIFLUOROMETHYL)PHENOXY)PHENYL)-3-(4-METHOXYPHENYL)-4,5-DIHYDRO-1H-PYRAZOL-1-YL)ETHANONE; 1-(5-(5-CHLORO-2-(2,6-DINITRO-4-(TRIFLUOROMETHYL)PHENOXY)PHENYL)-3-(P-TOLYL)-4,5-DIHYDRO-1H-PYRAZOL-1-YL)ETHANONE; 1 (5 (3,5 DICHLORO 2 (2,6 DINITRO 4 (TRIFLUOROMETHYL)PHENOXY)PHENYL) 3 (4 METHOXYPHENYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL)ETHANONE; 1 (5 (5 CHLORO 2 (2,6 DINITRO 4 (TRIFLUOROMETHYL)PHENOXY)PHENYL) 3 (P TOLYL) 4,5 DIHYDRO 1H PYRAZOL 1 YL)ETHANONE; ANTIINFECTIVE AGENT; DIPHENYL ETHER DERIVATIVE; DNA TOPOISOMERASE (ATP HYDROLYSING); GYRASE INHIBITOR; PYRAZOLE DERIVATIVE;

ARTICLE; BACILLUS SUBTILIS; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECT; ENZYMOLOGY; ESCHERICHIA COLI; METABOLISM; MICROBIAL SENSITIVITY TEST; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; BACILLUS SUBTILIS; DNA GYRASE; DOSE-RESPONSE RELATIONSHIP, DRUG; ESCHERICHIA COLI; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHENYL ETHERS; PSEUDOMONAS AERUGINOSA; PYRAZOLES; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP; TOPOISOMERASE II INHIBITORS;

EID: 84892586388     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c3ob41953c     Document Type: Article

References (34)

1. J. Wang et al. Nature 2006 441 358 361
2. M. Leeb Nature 2004 431 892 893
3. R. J. Reece A. Maxwell Crit. Rev. Biochem. Mol. Biol. 1991 26 335 375
4. L. Gomez M. D. Hack J. Wu J. J. M. Wiener H. Venkatesan A. Santilln D. J. Pippel Jr. N. Mani B. J. Motley S. T. Morrow K. J. Shaw R. Wolin C. A. Grice T. K. Jones Bioorg. Med. Chem. Lett. 2007 17 2723 2727
5. T. Miyamoto J. Matsumoto K. Chiba H. Egawa K. Shibamori A. Minamida Y. Nishimura H. Okada M. Kataoka M. Fujita J. Med. Chem. 1990 33 1645 1656
6. T. P. Tran E. L. Ellsworth J. P. Sanchez B. M. Watson M. A. Stier H. D. Hollis Showalter J. M. Domagala M. A. Shapiro E. T. Joannides S. J. Gracheck D. Q. Nguyen P. Bird J. Sharadendu A. Yip C. Ha S. Ramezani X. Wuc R. Singh Bioorg. Med. Chem. Lett. 2007 17 1312 1320
7. A. Tanitame Y. Oyamada K. Ofuji Y. Kyoya K. Suzuki H. Ito M. Kawasaki K. Nagai M. Wachid J. I. Yamagishi Bioorg. Med. Chem. Lett. 2004 14 2857 2862
8. A. A. Bekhita T. Abdel-Aziem Bioorg. Med. Chem. 2004 12 1935 1945
9. A. Tanitame Y. Oyamada K. Ofuji M. Fujimoto K. Suzuki T. Ueda H. Terauchi M. Kawasaki K. Nagai M. Yamagishib J. I. Wachie Bioorg. Med. Chem. 2004 12 5515 5524
10. A. A. Bekhit H. M. A. Ashour Y. S. AbdelGhany A. E.-D. A. Bekhit A. Baraka Eur. J. Med. Chem. 2008 43 456 463
11. X.-H. Liu B.-F. Ruan J.-X. Liu B.-A. Song L.-H. Jing J. Li Y. Yang X.-B. Qi H.-L. Zhu Bioorg. Med. Chem. Lett. 2011 21 2916 2920
12. R. G. Ridley W. Hofheinz H. Matile C. Jaquet A. Dorn R. Masciadri S. Jolidon W. F. Richter A. Guenzi M. A. Girometta H. Urwyler W. Huber S. Thaithong W. Peters Antimicrob. Agents Chemother. 1996 40 1846 1854
13. D. Y. D. De F. M. Krogstad L. D. Byers D. J. Krogstad J. Med. Chem. 1998 41 4918 4926
14. D. Azarifar H. Ghasemnejad Molecules 2003 8 642 648
15. X.-H. Liu J. Zhu A.-n. Zhou B.-A. Song H.-L. Zhu L.-S. bai P. S. Bhadury C.-X. Pan Bioorg. Med. Chem. 2009 17 1207 1213
16. R. N. Comber R. J. Gray J. A. Secrist Carbohydr. Res. 1991 216 441 452
17. H. J. Boehm M. Boehringer D. Bur H. Gmuender W. Huber W. Klaus D. Kostrewa H. Kuehne T. Lübbers M. K. Nathalie F. Mueller J. Med. Chem. 2000 43 2664 2674
18. T. Lübbers P. Angehrn H. Gmunder S. Herzig J. Kulhanek Bioorg. Med. Chem. Lett. 2000 10 821 826
19. A. Tanitame Y. Oyamada K. Ofuji M. Fujimoto N. Iwai Y. Hiyama K. Suzuki H. Ito H. Terauchi M. Kawasaki K. Nagai M. Wachi J. I. Yamagishi J. Med. Chem. 2004 47 3693 3696
20. J. Sun P. C. Lv Y. Yin R. J. Yuan J. Ma H. L. Zhu PLoS One 2013 8 e69751
21. K. L. Kees J. J. Fitzgerald K. E. Steimer J. F. Mattes B. Mihan T. Tosi D. Mondoro M. L. McCaleb J. Med. Chem. 1996 39 3920 3928
22. T. P. Gregory C. D. Darlene M. S. David Pestic. Biochem. Physiol. 1998 60 177 186
23. S. G. Kucukguzel S. Rollas H. Erdeniz A. C. Kiraz M. Ekinci A. Vidin Eur. J. Med. Chem. 2000 35 761 771
24. S. M. Ronkin M. Badia S. Bellon A. L. Grillot C. H. Gross T. H. Grossman N. Mani J. D. Parsons D. Stamos M. Trudeau Y. Wei P. S. Charifson Bioorg. Med. Chem. Lett. 2010 20 2828 2831
25. J. D. MacLowry M. J. Jaqua S. T. Selepak Appl. Microbiol. 1970 20 46 53
26. F. Smaill J. Can Gastroenterology 2000 14 871 875
27. J.-Y. Lee K.-W. Jeong S. Shin J.-U. Lee Y. Kim Eur. J. Med. Chem. 2012 47 261 269
28. X. He M. R. Anne R. D. Umesh E. K. Glen A. R. Kevin Antimicrob. Agents Chemother. 2004 48 3093 3102
29. P. Kirkpatrick Nat. Rev. Drug Discovery 2004 3 299 299
30. F. Blanche B. Cameron F. Bernard L. Maton B. Manse L. Ferro N. Ratet C. Lecoq A. Goniot D. Bisch J. Crouzet Antimicrob. Agents Chemother. 1996 40 2714 2720
31. K. Sato Y. Inoue T. Fujii H. Anoyama M. Inoue S. Mitsuhashi Antimicrob. Agents Chemother. 1990 34 1088 1097
32. O. Elisha L. S. Walter J. Bacteriol. 1982 151 524 535
33. U.S. National Library of Medicine, Toxicology Data Network (Toxnet), 2011. Available from http://toxnet.nlm.nih.gov/
34. G. S. Wu D. H. Robertson C. L. Brooks M. Vieth J. Comput. Chem. 2003 24 1549 1562