Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring

Bioorganic and Medicinal Chemistry

Volumn 12, Issue 21, 2004, Pages 5515-5524

  Tanitame, Akihiko ^a   Oyamada, Yoshihiro ^a   Ofuji, Keiko ^a   Fujimoto, Mika ^a   Suzuki, Kenji ^a   Ueda, Tomohiko ^a   Terauchi, Hideo ^a   Kawasaki, Motoji ^a   Nagai, Kazuo ^b   Wachi, Masaaki ^c   Yamagishi, Jun Ichi ^a  

^a DAINIPPON SUMITOMO PHARMA CO LTD   (Japan)

^b CHUBU UNIVERSITY   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

DNA gyrase inhibitor; Multidrug resistant strains; Pyrazole, oxazole and imidazole derivatives

Indexed keywords

1 (3 CHLOROPHENYL) 3 (4 PHENOXYPHENYL) 5 (3 PIPERIDYL)PYRAZOLE; 1 (3 CHLOROPHENYL) 3 (N METHYLAMINOMETHYL) 5 (4 PHENOXYPHENYL)PYRAZOLE FUMARATE; 1 (3 CHLOROPHENYL) 3 [3 (N METHYL)AMINOPROPYL] 5 (4 PHENOXYPHENYL)PYRAZOLE; 1 (3 CHLOROPHENYL) 5 (4 PHENOXYPHENYL) 3 (2 PIPERIDYL)PYRAZOLE; 1 (3 CHLOROPHENYL) 5 (4 PHENOXYPHENYL) 3 (3 PIPERIDYL)PYRAZOLE; 1 (3 CHLOROPHENYL) 5 (4 PHENOXYPHENYL) 3 (4 PIPERIDYL)PYRAZOLE; 1 (3 CHLOROPHENYL) 5 (N METHYLAMINOMETHYL) 3 (4 PHENOXYPHENYL)PYRAZOLE; 1 [(TERT BUTOXYCARBONYL) N METHYL]AMINO 4 (4 PHENOXYPHENYL)BUTANE 2,4 DIONE; 1 [(TERT BUTOXYCARBONYL) N METHYL]AMINO 6 (4 PHENOXYPHENYL)HEXANE 4,6 DIONE; 1 [N BENZYL(TERT BUTOXYCARBONYL)]AMINO 4 (4 PHENOXYPHENYL)BUTANE 2,4 DIONE; 1 CYCLOHEXYL 3 (4 PHENOXYPHENYL)PROPANE 1,3 DIONE; 3 (N BENZYLAMINOMETHYL) 1 (3 CHLOROPHENYL) 5 (4 PHENOXYPHENYL)PYRAZOLE; 5 (3 BENZYLOXYPHENYL) 1 (3 CHLOROPHENYL) 3 (4 PIPERIDYL)PYRAZOLE; AMPICILLIN; ANTIINFECTIVE AGENT; CLARITHROMYCIN; COUMARIN; DNA TOPOISOMERASE IV; GYRASE INHIBITOR; IMIDAZOLE DERIVATIVE; NOVOBIOCIN; OXAZOLE DERIVATIVE; PYRAZOLE DERIVATIVE; QUINOLONE; SPARFLOXACIN; TERT BUTYL 2 [1,3 DIOXO 3 (4 PHENOXYPHENYL)PROPYL]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 3 [1,3 DIOXO 3 (4 PHENOXYPHENYL) 1 PROPYL]PIPERIDINE 1 CARBOXYLATE; TERT BUTYL 4 [3 (3 BENZYLOXYPHENYL) 1,3 DIOXO 1 PROPYL]PIPERIDINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VANCOMYCIN;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL STRAIN; DRUG POTENCY; DRUG SYNTHESIS; GRAM POSITIVE BACTERIUM; LABORATORY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ANTI-BACTERIAL AGENTS; AZOLES; DNA GYRASE; ENZYME INHIBITORS; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS;

POSIBACTERIA;

EID: 4644248307     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2004.08.010     Document Type: Article

References (27)

1. S.J. Brickner, D.K. Hutchinson, M.R. Barbachyn, P.R. Manninen, D.A. Ulanowicz, S.A. Garmon, K.C. Grega, S.K. Hendges, D.S. Toops, C.W. Ford, and G.E. Zurenko J. Med. Chem. 39 1996 673 679
2. L. Ferrero, B. Cameron, B. Manse, D. Lagneaux, J. Crouzet, A. Famechon, and F. Blanche Mol. Microbiol. 13 1994 641 653
3. O.K. Kim, and K.A. Ohemeng Expert Opin. Ther. Pat. 8 1998 959 969
4. T. Miyamoto, J. Matsumoto, K. Chiba, H. Egawa, K. Shibamori, A. Minamida, Y. Nishimura, H. Okada, M. Kataoka, M. Fujita, T. Hirose, and J. Nakano J. Med. Chem. 33 1990 1645 1656
5. A. Maxwell Mol. Microbiol. 9 1993 681 686
6. N. Nakada, H. Gmuender, T. Hirata, and M. Arisawa Antimicrob. Agents Chemother. 38 1994 1966 1973
7. N. Nakada, H. Gmunder, T. Hirata, and M. Arisawa J. Biol. Chem. 270 1995 14286 14291
8. J. Rudolph, H. Theis, R. Hanke, R. Endermann, L. Johannsen, and F. Geschke J. Med. Chem. 44 2001 619 626
9. P. Angehrn, S. Buchmann, C. Funk, E. Goetschi, H. Gmuender, P. Hebeisen, D. Kostrewa, H. Link, T. Luebbers, R. Masciadri, J. Nielsen, P. Reindl, F. Ricklin, A. Schmitt-Hoffmann, and F. Theil J. Med. Chem. 47 2004 1487 1513
10. H. Boehm, M. Boehringer, D. Bur, H. Gmuender, W. Hunber, W. Klaus, D. Kostrewa, H. Kuehne, T. Luebbers, N. Meunier-Keller, and F. Mueller J. Med. Chem. 43 2000 2664 2674
11. T. Lubbers, P. Angehrn, H. Gmunder, S. Herzig, and J. Kulhanek Bioorg. Med. Chem. Lett. 10 2000 821 826
12. U. Galm, S. Heller, S. Shapiro, M. Page, S. Li, and L. Heide Antimicrob. Agents Chemother. 48 2004 1307 1312
13. A. Tanitame, Y. Oyamada, K. Ofuji, Y. Kyoya, K. Suzuki, H. Ito, M. Kawasaki, K. Nagai, M. Wachi, and J. Yamagishi Bioorg. Med. Chem. Lett. 14 2004 2857 2862
14. A. Tanitame, Y. Oyamada, K. Ofuji, K. Suzuki, H. Ito, M. Kawasaki, M. Wachi, and J. Yamagishi Bioorg. Med. Chem. Lett. 14 2004 2863 2866
15. M. Wachi, N. Iwai, A. Kunihisa, and K. Nagai Biochimie 81 1999 909 913
16. S. Hiraga, H. Niki, T. Ogura, C. Ichinose, H. Mori, B. Ezaki, and A. Jaffe J. Bacteriol. 171 1989 1496 1505
17. A. Tanitame, Y. Oyamada, K. Ofuji, M. Fujimoto, N. Iwai, Y. Hiyama, K. Suzuki, H. Ito, H. Terauchi, M. Kawasaki, K. Nagai, M. Wachi, and J. Yamagishi J. Med. Chem. 14 2004 3693 3696
18. M. Rowley, H.B. Broughton, I. Collins, R. Baker, F. Emms, R. Marwood, S. Patel, S. Patel, C.I. Ragan, S.B. Freedman, and P.D. Leeson J. Med. Chem. 39 1996 1943 1945
19. M. Rowley, I. Collins, H.B. Broughton, W.B. Davey, R. Baker, F. Emms, R. Marwood, S. Patel, S. Patel, C.I. Ragan, S.B. Freedman, R. Ball, and P.D. Leeson J. Med. Chem. 40 1997 2374 2385
20. J.F. Cameron, C.G. Willson, and J.M.J. Frechet J. Chem. Soc., Perkin Trans. 1 16 1997 2429 2442
21. N.A. Meanwell, M.J. Rosenfeld, A.K. Trehan, J.L. Romine, J.J.K. Wright, C.L. Brassard, J.O. Buchanan, M.E. Federici, J.S. Fleming, M. Gamberdella, G.B. Zavoico, and S.M. Seiler J. Med. Chem. 35 1992 3498 3512
22. M.F. Brackeen, J.A. Stafford, P.L. Feldman, and D.S. Karanewsky Tetrahedron Lett. 35 1994 1635 1638
23. K. Sato, Y. Inoue, T. Fujii, H. Aoyama, M. Inoue, and S. Mitsuhashi Antimicrob. Agents Chemother. 30 1986 777 780
24. H. Peng, and K.J. Marians J. Biol. Chem. 268 1993 24481 24490
25. M. Stieger, P. Angehrn, B. Wohlgensinger, and H. Gmunder Antimicrob. Agents Chemother. 40 1996 1060 1062
26. N.G. Galakatos, and D.S. Kemp J. Org. Chem. 50 1985 1302 1304
27. W.J. Hoekstra, B.E. Maryanoff, B.P. Damiano, P. Andrade-Gordon, J.H. Cohen, M.J. Costanzo, B.J. Haertlein, L.R. Hecker, B.L. Hulshizer, J.A. Kauffman, P. Keane, D.F. McComsey, J.A. Mitchell, L. Scott, R.D. Shah, and S.C. Yabut J. Med. Chem. 42 1999 5254 5265