Structure-activity relationships of antibacterial 6, 7-and 7, 8-disubstituted 1-alkyl-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids

…, A Itoh, S Murayama, S Suzue, T Irikura

Index: Koga, Hiroshi; Itoh, Akira; Murayama, Satoshi; Suzue, Seigo; Irikura, Tsutomu Journal of Medicinal Chemistry, 1980 , vol. 23, # 12 p. 1358 - 1363

Full Text: HTML

Citation Number: 546

Abstract

Previous quantitative and qualitative structure-activity studies in antibacterial monosubstituted l-ethyl-1, 4-di-hydro-4-oxoquinoline-3-carboxylic acids prompted us to synthesize the 6, 7, 8-polysubstituted compounds. In this paper, the preparation and antibacterial activity of the 6, 7-and 7, 8-disubstituted compounds and their derivatives are described. Among these compounds, l-ethyl-6-fluoro-1, 4-dihydro-4-oxo-7-(l-piperazinyl) ...

 Related Synthetic Route
Piperazine Structure

110-85-0

Piperazine

6,7-dichloro-1-ethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid Structure

67681-88-3

6,7-dichloro-1-...

~64%

6-chloro-1-ethyl-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid Structure

67681-84-9

6-chloro-1-ethy...

ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate Structure

70458-93-4

ethyl 7-chloro-...

Ethyl iodide Structure

75-03-6

Ethyl iodide

~91%

ETHYL 7-CHLORO-1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-QUINOLINE-5-CARBOXYLATE Structure

70458-94-5

ETHYL 7-CHLORO-...

Diethyl ethoxymethylenemalonate Structure

87-13-8

Diethyl ethoxym...

~%

ETHYL 7-CHLORO-1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-QUINOLINE-5-CARBOXYLATE Structure

70458-94-5

ETHYL 7-CHLORO-...

Norfloxacin Structure

70458-96-7

Norfloxacin

allyl bromide Structure

106-95-6

allyl bromide

~90%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

3-Chloro-4-fluoroaniline Structure

367-21-5

3-Chloro-4-fluo...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid Structure

68077-26-9

7-Chloro-1-ethy...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

ETHYL 7-CHLORO-1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-QUINOLINE-5-CARBOXYLATE Structure

70458-94-5

ETHYL 7-CHLORO-...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

ethyl 1-ethyl-6-fluoro-7-(piperazin-1-yl)-4(1H)-quinolone-3-carboxylate Structure

74011-47-5

ethyl 1-ethyl-6...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate Structure

70032-30-3

diethyl [[(3-ch...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate Structure

70458-93-4

ethyl 7-chloro-...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

ethyl 6-fluoro-4-hydroxy-7-(piperazin-1-yl)quinoline-3-carboxylate Structure

75001-56-8

ethyl 6-fluoro-...

~%

1-ethyl-6-fluoro-4-oxo-7-(4-prop-2-enylpiperazin-1-yl)quinoline-3-carboxylic acid Structure

70458-97-8

1-ethyl-6-fluor...

Ethanoic anhydride Structure

108-24-7

Ethanoic anhydride

Norfloxacin Structure

70458-96-7

Norfloxacin

~97%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

3-Chloro-4-fluoroaniline Structure

367-21-5

3-Chloro-4-fluo...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

diethyl [[(3-chloro-4-fluorophenyl)amino]methylene]malonate Structure

70032-30-3

diethyl [[(3-ch...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate Structure

70458-93-4

ethyl 7-chloro-...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

ethyl 6-fluoro-4-hydroxy-7-(piperazin-1-yl)quinoline-3-carboxylate Structure

75001-56-8

ethyl 6-fluoro-...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid Structure

68077-26-9

7-Chloro-1-ethy...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

ETHYL 7-CHLORO-1-ETHYL-6-FLUORO-1,4-DIHYDRO-4-OXO-QUINOLINE-5-CARBOXYLATE Structure

70458-94-5

ETHYL 7-CHLORO-...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

ethyl 1-ethyl-6-fluoro-7-(piperazin-1-yl)-4(1H)-quinolone-3-carboxylate Structure

74011-47-5

ethyl 1-ethyl-6...

~%

7-(4-acetylpiperazin-1-yl)-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

74011-56-6

7-(4-acetylpipe...

Norfloxacin Structure

70458-96-7

Norfloxacin

methyl iodide Structure

74-88-4

methyl iodide

~29%

Pefloxacin Structure

70458-92-3

Pefloxacin

Formaldehyde Structure

50-00-0

Formaldehyde

Norfloxacin Structure

70458-96-7

Norfloxacin

~84%

Pefloxacin Structure

70458-92-3

Pefloxacin

methylpiperazine Structure

109-01-3

methylpiperazine

7-Chloro-1-ethyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic Acid Structure

68077-26-9

7-Chloro-1-ethy...

~68%

Pefloxacin Structure

70458-92-3

Pefloxacin

3-Chloro-4-fluoroaniline Structure

367-21-5

3-Chloro-4-fluo...

~%

ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate Structure

70458-93-4

ethyl 7-chloro-...

Diethyl ethoxymethylenemalonate Structure

87-13-8

Diethyl ethoxym...

~%

ethyl 7-chloro-6-fluoro-4-hydroxyquinoline-3-carboxylate Structure

70458-93-4

ethyl 7-chloro-...

ethyl 7-Chloro-4-hydroxy-6-nitro-3-quinolinecarboxylate Structure

75001-48-8

ethyl 7-Chloro-...

~99%

3-(4-ACETYL-PIPERAZIN-1-YL)-4-FLUOROANILINE Structure

75001-84-2

3-(4-ACETYL-PIP...

1-(2-Fluorophenyl)piperazine Structure

1011-15-0

1-(2-Fluorophen...

~%

3-(4-ACETYL-PIPERAZIN-1-YL)-4-FLUOROANILINE Structure

75001-84-2

3-(4-ACETYL-PIP...

1-(4-(2-fluorophenyl)piperazin-1-yl)ethan-1-one Structure

75012-63-4

1-(4-(2-fluorop...

~%

3-(4-ACETYL-PIPERAZIN-1-YL)-4-FLUOROANILINE Structure

75001-84-2

3-(4-ACETYL-PIP...

3-Chloro-2-fluoroaniline Structure

2106-04-9

3-Chloro-2-fluo...

~%

7-chloro-1-ethyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Structure

75001-60-4

7-chloro-1-ethy...

Ethyl 7-chloro-8-fluoro-4-hydroxyquinoline-3-carboxylate Structure

75001-54-6

Ethyl 7-chloro-...

~%

7-chloro-1-ethyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Structure

75001-60-4

7-chloro-1-ethy...

diethyl 2-(((3-chloro-2-fluorophenyl)amino)methylene)malonate Structure

345625-45-8

diethyl 2-(((3-...

~%

7-chloro-1-ethyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Structure

75001-60-4

7-chloro-1-ethy...

ethyl 7-chloro-1-ethyl-8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate Structure

345221-07-0

ethyl 7-chloro-...

~%

7-chloro-1-ethyl-8-fluoro-4-oxoquinoline-3-carboxylic acid Structure

75001-60-4

7-chloro-1-ethy...

7-amino-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester Structure

91188-89-5

7-amino-1-ethyl...

~%

7-amino-1-ethyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Structure

75001-63-7

7-amino-1-ethyl...


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