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Volumn 8, Issue 7, 2013, Pages

Synthesis, Structure and Antibacterial Activity of Potent DNA Gyrase Inhibitors: N′-Benzoyl-3-(4-Bromophenyl)-1H-Pyrazole-5-Carbohydrazide Derivatives

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 BROMOPHENYL) 1H PYRAZOLE 5 CARBOHYDRAZIDE; DNA TOPOISOMERASE (ATP HYDROLYSING); ETHYL 4 (4 BROMOPHENYL) 2,4 DIOXOBUTANOATE; GYRASE INHIBITOR; N9 BENZOYL 3 (4 BROMOPHENYL) 1H PYRAZOLE 5 CARBOHYDRAZIDE DERIVATIVE; NOVOBIOCIN; PENICILLIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84880805844     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0069751     Document Type: Article
Times cited : (27)

References (29)
  • 2
    • 0028855453 scopus 로고
    • Effect of pyrimido [1,6-a] benzimidazoles, quinolones, and Ca2+ on the DNA gyrase-mediated cleavage reaction
    • Gmünder H, Kuratli K, Keck W, (1995) Effect of pyrimido [1,6-a] benzimidazoles, quinolones, and Ca2+ on the DNA gyrase-mediated cleavage reaction. Antimicrob Agents Chemother 39: 163-169.
    • (1995) Antimicrob Agents Chemother , vol.39 , pp. 163-169
    • Gmünder, H.1    Kuratli, K.2    Keck, W.3
  • 3
    • 84864268953 scopus 로고    scopus 로고
    • Structure-Based Discovery of Substituted 4,5′-Bithiazoles as Novel DNA Gyrase Inhibitors
    • Matjaz B, Andrej P, Miha R, Gregor A, Dusan T, et al. (2012) Structure-Based Discovery of Substituted 4,5′-Bithiazoles as Novel DNA Gyrase Inhibitors. J Med Chem 55: 6413-6426.
    • (2012) J Med Chem , vol.55 , pp. 6413-6426
    • Matjaz, B.1    Andrej, P.2    Miha, R.3    Gregor, A.4    Dusan, T.5
  • 4
    • 82355173219 scopus 로고    scopus 로고
    • Exploiting bacterial DNA gyrase as a drug target: current state and perspectives
    • Collin Frédéric, Shantanu K, Anthony M, (2011) Exploiting bacterial DNA gyrase as a drug target: current state and perspectives. Appl Microbiol Biotechnol 92: 479-497.
    • (2011) Appl Microbiol Biotechnol , vol.92 , pp. 479-497
    • Collin, F.1    Shantanu, K.2    Anthony, M.3
  • 5
    • 84874468435 scopus 로고    scopus 로고
    • Application of a Novel Microtitre Plate-Based Assay for the Discovery of New Inhibitors of DNA Gyrase and DNA Topoisomerase VI
    • Taylor JA, Mitchenall LA, Rejzek M, Field RA, Maxwell A, (2013) Application of a Novel Microtitre Plate-Based Assay for the Discovery of New Inhibitors of DNA Gyrase and DNA Topoisomerase VI. PLoS ONE 8 (2):: e58010.
    • (2013) PLoS ONE , vol.8 , Issue.2
    • Taylor, J.A.1    Mitchenall, L.A.2    Rejzek, M.3    Field, R.A.4    Maxwell, A.5
  • 6
    • 76749106664 scopus 로고    scopus 로고
    • Molecular Modeling of Mycobacterium Tuberculosis DNA Gyrase and its Molecular Docking Study with Gatifloxacin Inhibitors
    • Elaine FFC, Edilaine FB, Aline AO, Teodorico CR, (2010) Molecular Modeling of Mycobacterium Tuberculosis DNA Gyrase and its Molecular Docking Study with Gatifloxacin Inhibitors. J Biomol Struct Dyn 27: 619-625.
    • (2010) J Biomol Struct Dyn , vol.27 , pp. 619-625
    • Elaine, F.F.C.1    Edilaine, F.B.2    Aline, A.O.3    Teodorico, C.R.4
  • 8
    • 0012684806 scopus 로고    scopus 로고
    • The ATP-binding site of type II topoisomerases as a target for antibacterial drugs
    • Maxwell A, Lawson DM, (2003) The ATP-binding site of type II topoisomerases as a target for antibacterial drugs. Curr Top Med Chem 3: 283-303.
    • (2003) Curr Top Med Chem , vol.3 , pp. 283-303
    • Maxwell, A.1    Lawson, D.M.2
  • 9
    • 0030005040 scopus 로고    scopus 로고
    • GyrB mutations in Staphylococcus aureus strains resistant to cyclothialidine, coumermycin, and novobiocin
    • Stieger M, Angehrn P, Wohlgensinger B, Gmunder H, (1996) GyrB mutations in Staphylococcus aureus strains resistant to cyclothialidine, coumermycin, and novobiocin. Antimicrob Agents Chemother 40: 1060-1062.
    • (1996) Antimicrob Agents Chemother , vol.40 , pp. 1060-1062
    • Stieger, M.1    Angehrn, P.2    Wohlgensinger, B.3    Gmunder, H.4
  • 10
    • 0025313814 scopus 로고
    • Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency
    • Miyamoto T, Matsumoto J, Chiba K, Egawa H, Shibamori K, et al. (1990) Synthesis and structure-activity relationships of 5-substituted 6,8-difluoroquinolones, including sparfloxacin, a new quinolone antibacterial agent with improved potency. J Med Chem 33: 1645-1656.
    • (1990) J Med Chem , vol.33 , pp. 1645-1656
    • Miyamoto, T.1    Matsumoto, J.2    Chiba, K.3    Egawa, H.4    Shibamori, K.5
  • 11
    • 33846897468 scopus 로고    scopus 로고
    • Structure-activity relationships of 3-aminoquinazolinediones, a new class of bacterial type-2 topoisomerase (DNA gyrase and topo IV) inhibitors
    • Tran TP, Ellsworth EL, Sanchez JP, Watson BM, Stier MA, et al. (2007) Structure-activity relationships of 3-aminoquinazolinediones, a new class of bacterial type-2 topoisomerase (DNA gyrase and topo IV) inhibitors. Bioorg Med Chem Lett 17: 1312-1320.
    • (2007) Bioorg Med Chem Lett , vol.17 , pp. 1312-1320
    • Tran, T.P.1    Ellsworth, E.L.2    Sanchez, J.P.3    Watson, B.M.4    Stier, M.A.5
  • 12
    • 3042552189 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors. Pyrazole derivatives
    • Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Iwai N, et al. (2004) Synthesis and antibacterial activity of a novel series of potent DNA gyrase inhibitors. Pyrazole derivatives. J Med Chem 47: 3693-3696.
    • (2004) J Med Chem , vol.47 , pp. 3693-3696
    • Tanitame, A.1    Oyamada, Y.2    Ofuji, K.3    Fujimoto, M.4    Iwai, N.5
  • 13
    • 2342485135 scopus 로고    scopus 로고
    • Design, synthesis and structure-activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity
    • Tanitame A, Oyamada Y, Ofuji K, Kyoya Y, Suzuki K, et al. (2004) Design, synthesis and structure-activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity. Bioorg Med Chem Lett 14: 2857-2862.
    • (2004) Bioorg Med Chem Lett , vol.14 , pp. 2857-2862
    • Tanitame, A.1    Oyamada, Y.2    Ofuji, K.3    Kyoya, Y.4    Suzuki, K.5
  • 14
    • 1642461641 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents
    • Bekhita AA, Abdel-Aziem T, (2004) Design, synthesis and biological evaluation of some pyrazole derivatives as anti-inflammatory-antimicrobial agents. Bioorg Med Chem 12: 1935-1945.
    • (2004) Bioorg Med Chem , vol.12 , pp. 1935-1945
    • Bekhita, A.A.1    Abdel-Aziem, T.2
  • 15
    • 4644248307 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring
    • Tanitame A, Oyamada Y, Ofuji K, Fujimoto M, Suzuki K, et al. (2004) Synthesis and antibacterial activity of novel and potent DNA gyrase inhibitors with azole ring. Bioorg Med.Chem 12: 5515-5524.
    • (2004) Bioorg Med.Chem , vol.12 , pp. 5515-5524
    • Tanitame, A.1    Oyamada, Y.2    Ofuji, K.3    Fujimoto, M.4    Suzuki, K.5
  • 16
    • 40049108415 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents
    • Bekhit AA, Ashour HMA, Abdel Ghany YS, Bekhit AE-DA, Baraka A, (2008) Synthesis and biological evaluation of some thiazolyl and thiadiazolyl derivatives of 1H-pyrazole as anti-inflammatory antimicrobial agents. Eur J Med Chem 43: 456-463.
    • (2008) Eur J Med Chem , vol.43 , pp. 456-463
    • Bekhit, A.A.1    Ashour, H.M.A.2    Abdel Ghany, Y.S.3    Bekhit, A.E.-D.A.4    Baraka, A.5
  • 17
    • 1642288258 scopus 로고    scopus 로고
    • Novel Inhibitors of DNA Gyrase: 3D Structure Based Biased Needle Screening, Hit Validation by Biophysical Methods, and 3D Guided Optimization. A Promising Alternative to Random Screening
    • Boehm HJ, Boehringer M, Bur D, Gmuender H, Huber W, et al. (2000) Novel Inhibitors of DNA Gyrase: 3D Structure Based Biased Needle Screening, Hit Validation by Biophysical Methods, and 3D Guided Optimization. A Promising Alternative to Random Screening. J Med Chem 43: 2664-2674.
    • (2000) J Med Chem , vol.43 , pp. 2664-2674
    • Boehm, H.J.1    Boehringer, M.2    Bur, D.3    Gmuender, H.4    Huber, W.5
  • 18
    • 0342313482 scopus 로고    scopus 로고
    • Design, synthesis, and structure-activity relationship studies of ATP analogues as DNA gyrase inhibitors
    • Kulhanek
    • Lubbers T, Angehrn P, Gmunder H, Herzig S, (2000) Kulhanek (2000) Design, synthesis, and structure-activity relationship studies of ATP analogues as DNA gyrase inhibitors. Bioorg Med Chem Lett 10: 821-826.
    • (2000) Bioorg Med Chem Lett , vol.10 , pp. 821-826
    • Lubbers, T.1    Angehrn, P.2    Gmunder, H.3    Herzig, S.4
  • 19
    • 41649097951 scopus 로고    scopus 로고
    • Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4, 5-dihydropyrazol-1-yl) ethanone oxime ester derivatives
    • Liu XH, Cui P, Song BA, Bhadury PS, Zhu HL, et al. (2008) Synthesis, structure and antibacterial activity of novel 1-(5-substituted-3-substituted-4, 5-dihydropyrazol-1-yl) ethanone oxime ester derivatives. Bioorg Med Chem 16: 4075-4082.
    • (2008) Bioorg Med Chem , vol.16 , pp. 4075-4082
    • Liu, X.H.1    Cui, P.2    Song, B.A.3    Bhadury, P.S.4    Zhu, H.L.5
  • 20
    • 41149147203 scopus 로고    scopus 로고
    • Synthesis, structure, and antibacterial activity of novel 5-arylpyrazole derivatives
    • Liu XH, Li B, Zhu HL, Song BA, (2008) Synthesis, structure, and antibacterial activity of novel 5-arylpyrazole derivatives. Aust J Chem 61: 223-230.
    • (2008) Aust J Chem , vol.61 , pp. 223-230
    • Liu, X.H.1    Li, B.2    Zhu, H.L.3    Song, B.A.4
  • 21
    • 58949096498 scopus 로고    scopus 로고
    • Synthesis, structure and antibacterial activity of new 2-(1-(2-(substituted-phenyl)-5-methyloxazol-4-yl)-3-(2-substitued-phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-7-substitued-1,2,3,4-tetrahydroisoquinoline derivatives
    • Liu XH, Zhu J, Zhou AN, Song BA, Zhu HL, et al. (2009) Synthesis, structure and antibacterial activity of new 2-(1-(2-(substituted-phenyl)-5-methyloxazol-4-yl)-3-(2-substitued-phenyl)-4,5-dihydro-1H-pyrazol-5-yl)-7-substitued-1,2,3,4-tetrahydroisoquinoline derivatives. Bioorg Med Chem 17: 1207-1213.
    • (2009) Bioorg Med Chem , vol.17 , pp. 1207-1213
    • Liu, X.H.1    Zhu, J.2    Zhou, A.N.3    Song, B.A.4    Zhu, H.L.5
  • 22
    • 77955558444 scopus 로고    scopus 로고
    • Development of a sphingosine kinase 1 specific small-molecule inhibitor
    • Sharma AK, Sk UH, Gimbor MA, Hengst JA, Wang XJ, et al. (2010) Development of a sphingosine kinase 1 specific small-molecule inhibitor. Eur J Med Chem 45: 4149-4156.
    • (2010) Eur J Med Chem , vol.45 , pp. 4149-4156
    • Sharma, A.K.1    Sk, U.H.2    Gimbor, M.A.3    Hengst, J.A.4    Wang, X.J.5
  • 23
    • 34248595616 scopus 로고    scopus 로고
    • Tricarbamate of 1,3,5-triaminobenzene via Curtius rearrangement of trimesic acid and subsequent nitration
    • Davis MC, (2007) Tricarbamate of 1,3,5-triaminobenzene via Curtius rearrangement of trimesic acid and subsequent nitration. Synth Commun 37: 1457-1462.
    • (2007) Synth Commun , vol.37 , pp. 1457-1462
    • Davis, M.C.1
  • 24
    • 79961166359 scopus 로고    scopus 로고
    • Oxadiazole derivatives containing 1,4-benzodioxan as potential immunosuppressive agents against RAW264.7 cells
    • Sun J, Cao N, Zhang XM, Yang YS, Zhang YB, et al. (2011) Oxadiazole derivatives containing 1,4-benzodioxan as potential immunosuppressive agents against RAW264.7 cells. Bioorg Med Chem 19: 4895-4902.
    • (2011) Bioorg Med Chem , vol.19 , pp. 4895-4902
    • Sun, J.1    Cao, N.2    Zhang, X.M.3    Yang, Y.S.4    Zhang, Y.B.5
  • 25
    • 10544254692 scopus 로고    scopus 로고
    • Differential behaviors of Staphylococcus aureus and Escherichia coli type II DNA topoisomerases
    • Blanche F, Cameron B, Bernard F, Maton L, Manse L, et al. (1996) Differential behaviors of Staphylococcus aureus and Escherichia coli type II DNA topoisomerases. Antimicrob Agents Chenother 40: 2714-2720.
    • (1996) Antimicrob Agents Chenother , vol.40 , pp. 2714-2720
    • Blanche, F.1    Cameron, B.2    Bernard, F.3    Maton, L.4    Manse, L.5
  • 26
    • 0019904477 scopus 로고
    • Bacillus subtilis DNA gyrase: purification of subunits and reconstitution of supercoiling activity
    • Orr E, Staudenbauer WL, (1982) Bacillus subtilis DNA gyrase: purification of subunits and reconstitution of supercoiling activity. J Bacteriol 151: 524-527.
    • (1982) J Bacteriol , vol.151 , pp. 524-527
    • Orr, E.1    Staudenbauer, W.L.2
  • 27
    • 0041781898 scopus 로고    scopus 로고
    • Detailed analysis of grid-based molecular docking: A case study of CDOCKER-A CHARMm-based MD docking algorithm
    • Wu G, Robertson DH, Brooks CL, Vieth M, (2003) Detailed analysis of grid-based molecular docking: A case study of CDOCKER-A CHARMm-based MD docking algorithm. J Comput Chem 24: 1549-1562.
    • (2003) J Comput Chem , vol.24 , pp. 1549-1562
    • Wu, G.1    Robertson, D.H.2    Brooks, C.L.3    Vieth, M.4


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