메뉴 건너뛰기




Volumn 47, Issue 19, 2004, Pages 4693-4709

A prodrug approach toward the development of water soluble fluoroquinolones and structure-activity relationships of quinoline-3-carboxylic acids

Author keywords

[No Author keywords available]

Indexed keywords

3 QUINOLINECARBOXYLIC ACID DERIVATIVE; ALKALINE PHOSPHATASE; CARBOXYLIC ACID DERIVATIVE; CIPROFLOXACIN; CYCLOPROPANE; NALIDIXIC ACID; OFLOXACIN; PA 2789; PA 2808; PRODRUG; PYRROLIDINE DERIVATIVE; QUINOLONE DERIVATIVE; TOBRAMYCIN; TOSUFLOXACIN; UNCLASSIFIED DRUG;

EID: 4444282620     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0497895     Document Type: Article
Times cited : (43)

References (29)
  • 2
    • 0028316927 scopus 로고
    • Structure-activity and structure-side-effect relationships for the quinolone antibacterials
    • (a) Domagala, J. M. Structure-activity and structure-side-effect relationships for the quinolone antibacterials. J. Antimicrob. Chemother. 1994, 33, 685-706.
    • (1994) J. Antimicrob. Chemother. , vol.33 , pp. 685-706
    • Domagala, J.M.1
  • 3
    • 0035884910 scopus 로고    scopus 로고
    • Quinolone molecular structure-activity relationships: What have we learned about improving antimicrobial activity
    • (b) Peterson, L. R. Quinolone molecular structure-activity relationships: What have we learned about improving antimicrobial activity. Clin. Infect. Dis. 2001, 33, S180-S186.
    • (2001) Clin. Infect. Dis. , vol.33
    • Peterson, L.R.1
  • 4
    • 0033839497 scopus 로고    scopus 로고
    • The fluoroquinolone antibacterials: Past, present and future perspectives
    • (c) Applebaum, P. C.; Hunter, P. A. The fluoroquinolone antibacterials: past, present and future perspectives. Int. J. Antimicrob. Agents 2000, 16, 5-15.
    • (2000) Int. J. Antimicrob. Agents , vol.16 , pp. 5-15
    • Applebaum, P.C.1    Hunter, P.A.2
  • 5
    • 0034070653 scopus 로고    scopus 로고
    • Comparison of the fluoroquinolones based on pharmacokenetic and pharmacodynamic parameters
    • (d) Pickerill, K. E.; Paladino, J. A.; Schentag, J. J. Comparison of the fluoroquinolones based on pharmacokenetic and pharmacodynamic parameters. Pharmacotherapy 2000, 20, 417-428.
    • (2000) Pharmacotherapy , vol.20 , pp. 417-428
    • Pickerill, K.E.1    Paladino, J.A.2    Schentag, J.J.3
  • 6
    • 0032708146 scopus 로고    scopus 로고
    • Pharmacokenetics and pharmacodynamics of fluoroquinolones
    • (e) Turnridge, J. Pharmacokenetics and pharmacodynamics of fluoroquinolones. Drugs 1999, 58, 29-36.
    • (1999) Drugs , vol.58 , pp. 29-36
    • Turnridge, J.1
  • 7
    • 0032750067 scopus 로고    scopus 로고
    • Activity of newer fluoroquinolones in vitro against Gram-positive bacteria
    • (f) Eliopoulos, G. M. Activity of newer fluoroquinolones in vitro against Gram-positive bacteria. Drugs 1999, 58, 23-28.
    • (1999) Drugs , vol.58 , pp. 23-28
    • Eliopoulos, G.M.1
  • 8
    • 0032422691 scopus 로고    scopus 로고
    • An overview of the new fluoroquinolone antibiotics
    • (g) Bosso, J. A. An overview of the new fluoroquinolone antibiotics. J. Infect. Dis. Pharmacother. 1998, 3, 1-8.
    • (1998) J. Infect. Dis. Pharmacother. , vol.3 , pp. 1-8
    • Bosso, J.A.1
  • 9
    • 0032971470 scopus 로고    scopus 로고
    • Expanded activity and utility of the new fluoroquinolones: A review
    • (h) Blondeau, J. M. Expanded activity and utility of the new fluoroquinolones: a review. Clin. Ther. 1999, 21, 3-40.
    • (1999) Clin. Ther. , vol.21 , pp. 3-40
    • Blondeau, J.M.1
  • 11
    • 0031460693 scopus 로고    scopus 로고
    • The role of fluoroquinolones in respiratory tract infections
    • (j) Grossman, R. F. The role of fluoroquinolones in respiratory tract infections. J. Antimicrob. Chemother. 1997, 40, 59-62.
    • (1997) J. Antimicrob. Chemother. , vol.40 , pp. 59-62
    • Grossman, R.F.1
  • 12
    • 0024555842 scopus 로고
    • Structure-activity relationships of the fluoroquinolones
    • (k) Chu, D. T. W.; Fernandes, P. B. Structure-activity relationships of the fluoroquinolones. Antimicrob. Agents Chemother. 1989, 33, 131-135.
    • (1989) Antimicrob. Agents Chemother. , vol.33 , pp. 131-135
    • Chu, D.T.W.1    Fernandes, P.B.2
  • 13
    • 0035866965 scopus 로고    scopus 로고
    • Mechanisms of action of antimicrobials: Focus on fluoroquinolones
    • (a) Hooper, D. C. Mechanisms of action of antimicrobials: focus on fluoroquinolones. Clin. Infect. Dis. 2001, 32, S9-S15.
    • (2001) Clin. Infect. Dis. , vol.32
    • Hooper, D.C.1
  • 14
    • 0032856370 scopus 로고    scopus 로고
    • Mechanism of fluoroquinolone action
    • (b) Drlica, K. Mechanism of fluoroquinolone action. Curr. Opin. Microbiol. 1999, 2, 504-508.
    • (1999) Curr. Opin. Microbiol. , vol.2 , pp. 504-508
    • Drlica, K.1
  • 17
    • 0031036875 scopus 로고    scopus 로고
    • Lung alkaline phosphatase as a marker of fibrosis in chronic interstitial discorders
    • (b) Capelli, A.; Lusuardi, M.; Cerutti, C. G.; Donner, C. F. Lung alkaline phosphatase as a marker of fibrosis in chronic interstitial discorders. Am. J. Respir. Crit. Care Med. 1997, 155, 249-253.
    • (1997) Am. J. Respir. Crit. Care Med. , vol.155 , pp. 249-253
    • Capelli, A.1    Lusuardi, M.2    Cerutti, C.G.3    Donner, C.F.4
  • 18
    • 0033598377 scopus 로고    scopus 로고
    • Glycosylation of fluoroquinolones through direct and oxygenated polymethylene linkages as a sugar-mediated active transport system for antimicrobials
    • Jung, M. E.; Yang, E. C.; Vu, B. T.; Kiankarimi, M.; Spyrou, E.; Kaunitz, J. Glycosylation of fluoroquinolones through direct and oxygenated polymethylene linkages as a sugar-mediated active transport system for antimicrobials. J. Med. Chem. 1999, 42, 3899-3909.
    • (1999) J. Med. Chem. , vol.42 , pp. 3899-3909
    • Jung, M.E.1    Yang, E.C.2    Vu, B.T.3    Kiankarimi, M.4    Spyrou, E.5    Kaunitz, J.6
  • 19
    • 0025882895 scopus 로고
    • Recent developments in the field of quinolone antibacterial agents
    • Chu, D. T. W.; Fernandes, P. B. Recent developments in the field of quinolone antibacterial agents. Adv. Drug Res. 1991, 21, 39-144.
    • (1991) Adv. Drug Res. , vol.21 , pp. 39-144
    • Chu, D.T.W.1    Fernandes, P.B.2
  • 20
    • 0027447243 scopus 로고
    • A safe, economical method for the preparation of β-oxo esters
    • Clay, R. J.; Collom, T. A.; Karrick, G. L.; Wemple, J. A safe, economical method for the preparation of β-oxo esters. Synthesis 1993, 290-292.
    • (1993) Synthesis , pp. 290-292
    • Clay, R.J.1    Collom, T.A.2    Karrick, G.L.3    Wemple, J.4
  • 21
    • 0034840124 scopus 로고    scopus 로고
    • Manoharan, Muthiah A novel protecting strategy for internucleoside phosphate and phosphorothiate groups
    • (a) Guzaev, Andrei P.; Manoharan, Muthiah A novel protecting strategy for internucleoside phosphate and phosphorothiate groups. Nucleosides, Nucleotides Nucleic Acids 2001, 20, 1011-1014.
    • (2001) Nucleosides, Nucleotides Nucleic Acids , vol.20 , pp. 1011-1014
    • Guzaev, A.P.1
  • 22
    • 0033550261 scopus 로고    scopus 로고
    • Synthesis, reactivity and biochemical evaluation of 1,3-substituted azetidin-2-ones as enzyme inhibitors
    • (b) Beauve, C.; Bouchet, M.; Touillaux, R.; Fastrez, J. Marchand-Brynaert, J. Synthesis, reactivity and biochemical evaluation of 1,3-substituted azetidin-2-ones as enzyme inhibitors. Tetrahedron 1999, 55, 13301-13320.
    • (1999) Tetrahedron , vol.55 , pp. 13301-13320
    • Beauve, C.1    Bouchet, M.2    Touillaux, R.3    Fastrez, J.4    Marchand-Brynaert, J.5
  • 24
    • 0032711437 scopus 로고    scopus 로고
    • Comparative tolerability of the newer fluoroquinolone antibacterials
    • (b) Ball, P.; Mandell, L.; Yoshihito, N.; Tillotson, G. Comparative tolerability of the newer fluoroquinolone antibacterials. Drug Saf. 1999, 21, 407-421.
    • (1999) Drug Saf. , vol.21 , pp. 407-421
    • Ball, P.1    Mandell, L.2    Yoshihito, N.3    Tillotson, G.4
  • 25
    • 0027070672 scopus 로고
    • Fluoroquinolones: Relationships between structural variations, mammalian cell cytotoxicity and antimicrobial activity
    • (c) Suto, M. J.; Domagala, J. M.; Rolang, G. E.; Mailloux, G. B.; Cohen, M. A. Fluoroquinolones: relationships between structural variations, mammalian cell cytotoxicity and antimicrobial activity. J. Med. Chem. 1992, 35, 4745-4750.
    • (1992) J. Med. Chem. , vol.35 , pp. 4745-4750
    • Suto, M.J.1    Domagala, J.M.2    Rolang, G.E.3    Mailloux, G.B.4    Cohen, M.A.5
  • 26
    • 0028805042 scopus 로고
    • The synthesis, structure-activity, and structure-side effect relationships of a series of 8-alkoxy- and 5-amino-8-alkoxyquinolone antibacterial agents
    • Sanchez, J. P.; Gogliotti, R. D.; Domagala, J. M.; Gracheck, S. J.; Huband, M. D.; Sesnie, J. A.; Cohen, M. A.; Shapiro, M. A. The synthesis, structure-activity, and structure-side effect relationships of a series of 8-alkoxy- and 5-amino-8-alkoxyquinolone antibacterial agents. J. Med. Chem. 1995, 38, 4478-4487.
    • (1995) J. Med. Chem. , vol.38 , pp. 4478-4487
    • Sanchez, J.P.1    Gogliotti, R.D.2    Domagala, J.M.3    Gracheck, S.J.4    Huband, M.D.5    Sesnie, J.A.6    Cohen, M.A.7    Shapiro, M.A.8
  • 27
    • 0023939458 scopus 로고
    • Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinolone-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids
    • Sanchez, J. P.; Domagala, J. M.; Hagen, S. E.; Heifetz, C. L.; Hutt, M. P.; Nichols, J. B.; Trehan, A. K. Quinolone antibacterial agents. Synthesis and structure-activity relationships of 8-substituted quinolone-3-carboxylic acids and 1,8-naphthyridine-3-carboxylic acids. J. Med. Chem. 1988, 31, 989-991.
    • (1988) J. Med. Chem. , vol.31 , pp. 989-991
    • Sanchez, J.P.1    Domagala, J.M.2    Hagen, S.E.3    Heifetz, C.L.4    Hutt, M.P.5    Nichols, J.B.6    Trehan, A.K.7
  • 28
    • 0026507066 scopus 로고
    • Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7-(cycloalkylamino)- 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids
    • Bouzard, D.; Di Cesare, P.; Essiz, M.; Jacquet, J. P.; Ledoussal, B.; Remuzon, P. Kessler, R. E.; Fung-Tomc, J. Fluoronaphthyridines as antibacterial agents. 4. Synthesis and structure-activity relationships of 5-substituted-6-fluoro-7-(cycloalkylamino)-1,4-dihydro-4-oxo-1, 8-naphthyridine-3-carboxylic acids. J. Med. Chem. 1992, 35, 518-525.
    • (1992) J. Med. Chem. , vol.35 , pp. 518-525
    • Bouzard, D.1    Di Cesare, P.2    Essiz, M.3    Jacquet, J.P.4    Ledoussal, B.5    Remuzon, P.6    Kessler, R.E.7    Fung-Tomc, J.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.