메뉴 건너뛰기




Volumn 48, Issue 9, 2005, Pages 3194-3202

Synthesis and antibacterial activity of 1-(2-fluorovinyl)-7-substituted-4- quinolone-3-carboxylic acid derivatives, conformationally restricted analogues of fleroxacin

Author keywords

[No Author keywords available]

Indexed keywords

1 (2 FLUOROVINYL) 4 QUINOLONE 3 CARBOXYLIC ACID DERIVATIVE; 6 DIFLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 8 METHOXY 7 (4 METHYL 1 PIPERAZINYL) 4 OXO 3 QUINOLINECARBOXYLIC ACID; 6 FLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 7 (4 METHYL 1 PIPERAZINYL) 4 OXO 3 QUINOLINECARBOXYLIC ACID; 6,8 DIFLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 7 (4 METHYL 1 PIPERAZINYL) 4 OXO 3 QUINOLINECARBOXYLIC ACID; 7 (3 AMINO 1 PYRROLIDINYL) 6 FLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 4 OXO 3 QUINOLINECARBOXYLIC ACID; 7 (3 AMINO 1 PYRROLIDINYL) 6 FLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 8 METHOXY 4 OXO 3 QUINOLINECARBOXYLIC ACID; 7 (3 AMINO 1 PYRROLIDINYL) 6,8 DIFLUORO 1 (2 FLUOROVINYL) 1,4 DIHYDRO 4 OXO 3 QUINOLINECARBOXYLIC ACID; DNA TOPOISOMERASE (ATP HYDROLYSING); FLEROXACIN; UNCLASSIFIED DRUG;

EID: 18244378266     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0402061     Document Type: Article
Times cited : (92)

References (27)
  • 1
    • 0019252702 scopus 로고
    • Structure-activity relationships of antibacterial 6,7- and 7,8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinolone-3-carboxylic acids
    • Koga, H.; Itoh, A.; Murayama, S.; Suzue, S.; Irikura, T. Structure-Activity Relationships of Antibacterial 6,7- and 7,8-Disubstituted 1-Alkyl-1,4-dihydro-4-oxoquinolone-3-carboxylic Acids. J. Med. Chem. 1980, 23, 1358-1363.
    • (1980) J. Med. Chem. , vol.23 , pp. 1358-1363
    • Koga, H.1    Itoh, A.2    Murayama, S.3    Suzue, S.4    Irikura, T.5
  • 2
    • 0020679387 scopus 로고
    • In vitro antibacterial activity of bay 09867, a new quinolone derivative, compared with those of other antimicrobial agents
    • (a) Wise, R.; Andrews, J. M.; Edwards, L. J. In Vitro Antibacterial Activity of Bay 09867, a New Quinolone Derivative, Compared with Those of Other Antimicrobial Agents. Antimicrob. Agents Chemother. 1983, 23, 559-564.
    • (1983) Antimicrob. Agents Chemother. , vol.23 , pp. 559-564
    • Wise, R.1    Andrews, J.M.2    Edwards, L.J.3
  • 3
    • 84985278773 scopus 로고
    • Cycloaracylation of enamines, I. Synthesis of 4-quinolone-3-carboxylic acids
    • (b) Grohe, K.; Heitzer, H. Cycloaracylation of Enamines, I. Synthesis of 4-Quinolone-3-carboxylic Acids: Liebigs Ann. Chem. 1987, 29-37.
    • (1987) Liebigs Ann. Chem. , pp. 29-37
    • Grohe, K.1    Heitzer, H.2
  • 4
    • 0023340780 scopus 로고
    • Synthesis and antibacterial activity of optically active ofloxacin and its fluoromethyl derivative
    • (a) Atarashi, S.; Yokohama, S.; Yamamzaki, K.; Sakano, K.; Imamura, M.; Hayakawa, I. Synthesis and Antibacterial Activity of Optically Active Ofloxacin and Its Fluoromethyl Derivative. Chem. Pharm. Bull. 1987, 35, 1896-1902.
    • (1987) Chem. Pharm. Bull. , vol.35 , pp. 1896-1902
    • Atarashi, S.1    Yokohama, S.2    Yamamzaki, K.3    Sakano, K.4    Imamura, M.5    Hayakawa, I.6
  • 5
    • 18244403477 scopus 로고
    • Synthesis and antibacterial activity of optically active ofloxacin
    • (b) Une, T.; Fujimoto, T.; Sato, K.; Osada, Y. Synthesis and Antibacterial Activity of Optically Active Ofloxacin. Antimicrob. Agents Chemother. 1988, 32, 559-564.
    • (1988) Antimicrob. Agents Chemother. , vol.32 , pp. 559-564
    • Une, T.1    Fujimoto, T.2    Sato, K.3    Osada, Y.4
  • 6
    • 0026590968 scopus 로고
    • Recent advances in structure activity relationships in new quinolones
    • Mitsuhasi, S., Junker, E., Eds.; Progress in Drug Research; Birkhauser Verlag: Basel, Switzerland
    • (a) Asahina, Y.; Ishizaki, T.; Suzue, S. Recent advances in structure activity relationships in new quinolones. In Fluorinated Quinolones-New Quinolones Antimicrobials; Mitsuhasi, S., Junker, E., Eds.; Progress in Drug Research, Vol. 38; Birkhauser Verlag: Basel, Switzerland, 1992; pp 57-106.
    • (1992) Fluorinated Quinolones-New Quinolones Antimicrobials , vol.38 , pp. 57-106
    • Asahina, Y.1    Ishizaki, T.2    Suzue, S.3
  • 7
    • 0028316927 scopus 로고
    • Structure-activity and structure-side-effect relationships for the quinolone antibacterials
    • (b) Domagara, 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
    • Domagara, J.M.1
  • 8
    • 0027363729 scopus 로고
    • Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents
    • Atarashi, S.; Imamura, M.; Kimura, Y.; Yoshida, A.; Hayakawa, I.; Fluorocyclopropyl Quinolones. 1. Synthesis and Structure-Activity Relationships of 1-(2-Fluorocyclopropyl)-3-pyridonecarboxylic Acid Antibacterial Agents. J. Med. Chem. 1993, 36, 3444-3448.
    • (1993) J. Med. Chem. , vol.36 , pp. 3444-3448
    • Atarashi, S.1    Imamura, M.2    Kimura, Y.3    Yoshida, A.4    Hayakawa, I.5
  • 10
    • 33847799030 scopus 로고
    • New synthetic reactions. Sulfenylation and dehydrosulfenylations of esters and ketones
    • (a) Trost, B. M.; Salzmann, T. N.; Hiroi, K. New Synthetic Reactions. Sulfenylation and Dehydrosulfenylations of Esters and Ketones. J. Am. Chem. Soc. 1976, 98, 4887-4902.
    • (1976) J. Am. Chem. Soc. , vol.98 , pp. 4887-4902
    • Trost, B.M.1    Salzmann, T.N.2    Hiroi, K.3
  • 11
    • 0000086269 scopus 로고
    • Fluoromethyl phenyl slofoxide: Highly convenient synthesis of vinyl fluoride and fluoromethylketone
    • (b) Reutrakul, V.; Rukachaisirikul, V. Fluoromethyl Phenyl Slofoxide: Highly Convenient Synthesis of Vinyl Fluoride and Fluoromethylketone. Tetrahedron Lett. 1983, 24, 725-728.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 725-728
    • Reutrakul, V.1    Rukachaisirikul, V.2
  • 12
    • 0000970230 scopus 로고
    • The preparation of α-fluorosulfoxide and vinyl fluoride
    • (c) Purrington, S. T.; Pittman, J. H. The Preparation of α-Fluorosulfoxide and Vinyl Fluoride. Tetrahedron Lett. 1987, 28, 3901-3904.
    • (1987) Tetrahedron Lett. , vol.28 , pp. 3901-3904
    • Purrington, S.T.1    Pittman, J.H.2
  • 13
  • 14
    • 0025891731 scopus 로고
    • Ethyl phenylsulfenyl fluoroacetare, a new and versatile reagent for the preparation of α-fluoro-α,β-unsaturated carboxylic acid esters
    • (e) Allmendinger, T. Ethyl Phenylsulfenyl Fluoroacetare, a New and Versatile Reagent for the Preparation of α-Fluoro-α,β- unsaturated Carboxylic Acid Esters. Tetrahedron 1991, 47, 4905-4914.
    • (1991) Tetrahedron , vol.47 , pp. 4905-4914
    • Allmendinger, T.1
  • 15
    • 0028344397 scopus 로고
    • Nucleic acid related compounds. 80. Synthesis of 5′-s-(alkyl and aryl)-5′-fluoro-5′-thioadenosines with xenon difluoride or (diethylamino)sulfur trifluoride, hydrolysis in aqueous buffer, and inhibition of S-adenosyl-L-homocysteine hydrolase by derived "adenosine 5′-aldehyde" species
    • (f) Robins, M. J.; Wnuk, S. F.; Mullah, K. B.; Dalley, N. K. Nucleic Acid Related Compounds. 80. Synthesis of 5′-S-(Alkyl and aryl)-5′- fluoro-5′-thioadenosines with Xenon Difluoride or (Diethylamino)sulfur Trifluoride, Hydrolysis in Aqueous Buffer, and Inhibition of S-Adenosyl-L-homocysteine Hydrolase by Derived "Adenosine 5′-Aldehyde" Species. J. Org. Chem. 1994, 59, 544-555.
    • (1994) J. Org. Chem. , vol.59 , pp. 544-555
    • Robins, M.J.1    Wnuk, S.F.2    Mullah, K.B.3    Dalley, N.K.4
  • 16
    • 33845379580 scopus 로고
    • (Diethylamino)sulfur trifluoride in organic synthesis. 2. The transformation of sulfoxide to α-fluoro thioesters
    • McCarthy, J. R.; Peet, N. P.; LeTourneau, M. E.; Inbasekaran, M. (Diethylamino)sulfur Trifluoride in Organic Synthesis. 2. The Transformation of Sulfoxide to α-Fluoro Thioesters. J. Am. Chem. Soc. 1985, 107, 735-737.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 735-737
    • McCarthy, J.R.1    Peet, N.P.2    LeTourneau, M.E.3    Inbasekaran, M.4
  • 17
    • 2542438213 scopus 로고
    • Antimonyl(III) chloride exerts potent catalysis of the conversion of sulfoxide to α-fluoro thioesters with (diethylamino)sulfur trifluoride
    • Wnuk, S. F.; Robins, M. J. Antimonyl(III) Chloride Exerts Potent Catalysis of the Conversion of Sulfoxide to α-Fluoro Thioesters with (Diethylamino)sulfur Trifluoride. J. Org. Chem. 1990, 55, 4757-4760.
    • (1990) J. Org. Chem. , vol.55 , pp. 4757-4760
    • Wnuk, S.F.1    Robins, M.J.2
  • 18
    • 0026031926 scopus 로고
    • Negative hyperconjugation does not play an important role in α-fluoro sulfides: An experimental demonstration
    • Fujita, M.; Suzuki, M.; Ogata, K.; Ogura, K. Negative Hyperconjugation Does Not Play an Important Role in α-Fluoro Sulfides: An Experimental Demonstration. Tetrahedron Lett. 1991, 32, 1463-1466.
    • (1991) Tetrahedron Lett. , vol.32 , pp. 1463-1466
    • Fujita, M.1    Suzuki, M.2    Ogata, K.3    Ogura, K.4
  • 19
    • 18244408216 scopus 로고    scopus 로고
    • Reference 2b
    • (a) Reference 2b.
  • 20
    • 0023939458 scopus 로고
    • Structure-activity relationships of 8-substituted quinolone-3-carboxylic acid and 1,8-naphthylidine-3-carboxylic acids
    • (b) Sanchez, J. P.; Domagara, J. M.; Hagen, S. E.; Heifentz, C. L.; Hutt, M. P.; Nichols, J. B. Structure-Activity Relationships of 8-Substituted Quinolone-3-carboxylic Acid and 1,8-Naphthylidine-3-carboxylic Acids. J. Med. Chem. 1988, 31, 983-991.
    • (1988) J. Med. Chem. , vol.31 , pp. 983-991
    • Sanchez, J.P.1    Domagara, J.M.2    Hagen, S.E.3    Heifentz, C.L.4    Hutt, M.P.5    Nichols, J.B.6
  • 21
    • 18244391423 scopus 로고    scopus 로고
    • Preaparation of 8-Alkoxyquinolonecarbixylic Acids as Antibacterials with Selective Toxicity. EP230295
    • (c) Masuzawa, K.; Suzue, S.; Hirai, K.; Ishizaki, T. Preaparation of 8-Alkoxyquinolonecarbixylic Acids as Antibacterials with Selective Toxicity. EP230295.
    • Masuzawa, K.1    Suzue, S.2    Hirai, K.3    Ishizaki, T.4
  • 22
    • 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
    • (d) Sanchez, J. P.; Gogliotti, R. D.; Domagara, 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    Domagara, J.M.3    Gracheck, S.J.4    Huband, M.D.5    Sesnie, J.A.6    Cohen, M.A.7    Shapiro, M.A.8
  • 23
    • 0028019103 scopus 로고
    • Pyridonecarboxylic acids as antibacterial agents VIII. Synthesis and structure-activity relationships of 7-(1-aminocyclopropyl)-4-oxo-1,8- naphthylidine-3-carbixylic acids and 7-(1-Aminocyclopropyl)-4-oxoquinoline-3- carboxylic acids
    • Todo, Y.; Nitta, J.; Miyazima, M.; Fukuoka, Y.; Yamashiro, Y.; Nishida, N.; Saikawa, I.; Narita, H.; Pyridonecarboxylic Acids as Antibacterial Agents VIII. Synthesis and Structure-Activity Relationships of 7-(1-Aminocyclopropyl)- 4-oxo-1,8-naphthylidine-3-carbixylic Acids and 7-(1-Aminocyclopropyl)-4- oxoquinoline-3-carboxylic Acids. Chem. Pharm. Bull. 1994, 42, 2063-2070.
    • (1994) Chem. Pharm. Bull. , vol.42 , pp. 2063-2070
    • Todo, Y.1    Nitta, J.2    Miyazima, M.3    Fukuoka, Y.4    Yamashiro, Y.5    Nishida, N.6    Saikawa, I.7    Narita, H.8
  • 25
    • 0026100361 scopus 로고
    • Three-dimensional structure-activity relationships and receptor mapping of N1-substituents of quinolone antibacterials
    • (b) Ohta, M.; Koga, H. Three-Dimensional Structure-Activity Relationships and Receptor Mapping of N1-Substituents of Quinolone Antibacterials. J. Med. Chem. 1991, 34, 131-139.
    • (1991) J. Med. Chem. , vol.34 , pp. 131-139
    • Ohta, M.1    Koga, H.2
  • 26
    • 85004565366 scopus 로고
    • Japan Society of Chemotherapy. Chemotherapy 1981, 29, 76.
    • (1981) Chemotherapy , vol.29 , pp. 76
  • 27
    • 0035180501 scopus 로고    scopus 로고
    • Target preference of 15 quinolones against staphylococcus aureus, based on antibacterial activities and target inhibition
    • Takei, M.; Fukuda, H.; Kishii, R.; Hosaka, M.; Target Preference of 15 Quinolones against Staphylococcus aureus, Based on Antibacterial Activities and Target Inhibition. Antimicrob. Agents Chemother. 2001, 45, 3544-3547.
    • (2001) Antimicrob. Agents Chemother. , vol.45 , pp. 3544-3547
    • Takei, M.1    Fukuda, H.2    Kishii, R.3    Hosaka, M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.