99726-76-8

Basic information

• Product Name: 1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid
• Synonyms: 1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid;1-Ethyl-4-oxo-6-fluoro-7-(1-piperazinyl)-8-fluoro-1,4-dihydro-3-quinolinecarboxylic acid;1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)quinoline-3-carboxylic acid;1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-piperazino-3-quinolinecarboxylic acid;8-Fluoronorfloxacin;PD-0117731;Lomefloxacin Impurity 6
• CAS NO: 99726-76-8
• Molecular Formula: C₁₆H₁₇F₂N₃O₃
• Molecular Weight: 337.3213
• Mol File: 99726-76-8.mol

Chemical Properties

• Boiling Point: 544.2°Cat760mmHg
• Flash Point: 282.9°C
• Appearance: /
• Density: 1.395g/cm³
• Vapor Pressure: 1.12E-12mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: 1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid(99726-76-8)
• EPA Substance Registry System: 1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid(99726-76-8)

Safety Data

• Hazardous Substances Data: 99726-76-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-Ethyl-4-oxo-6,8-difluoro-7-piperazino-1,4-dihydroquinoline-3-carboxylic acid is used as an impurity in Lomefloxacin, a fluorinated quinolone antibacterial agent, for its role as a DNA gyrase antagonist, which helps in inhibiting bacterial growth and treating various infections.

InChI:InChI=1/C16H17F2N3O3/c1-2-20-8-10(16(23)24)15(22)9-7-11(17)14(12(18)13(9)20)21-5-3-19-4-6-21/h7-8,19H,2-6H2,1H3,(H,23,24)

Upstream product

• 110-85-0 piperazine 
• 75338-42-0 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 
• 100501-60-8 diethyl 2-((2,3,4-trifluorophenylamino)methylene)malonate 
• 79660-46-1 ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 100501-62-0 ethyl 1-ethyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylate 
• 3862-73-5 2,3,4-trifluoroaniline 

Downstream Products

• 353793-90-5 1-ethyl-7-{4-[2-(4-chlorophenyl)-2-oxoethyl]-1-piperazinyl}-6,8-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxykic acid 
• 353793-89-2 1-ethyl-6,8-difluoro-7-{4-[2-(4-fluorophenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 353793-91-6 1-ethyl-6,8-difluoro-7-{4-[2-(4-methoxyphenyl)-2-oxoethyl]-1-piperazinyl}-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 353793-88-1 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(4-phenacyl-1-piperazinyl)-quinoline-3-carboxylic acid 
• 158437-33-3 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(4-methylbenzenesulfonyl)-1-piperazinyl]-3-quinolinecarboxylic acid 
• 158437-31-1 1-ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-[4-(4-acetamidobenzenesulfonyl)-1-piperazinyl]-3-quinolinecarboxylic acid 
• 158437-32-2 1-Ethyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(4-benzenesulfonyl-1-piperazinyl)-3-quinolinecarboxylic acid 
• 1393927-87-1 C₃₀H₂₉F₂N₇O₄ 

Relevant articles and documents

Synthesis and antibacterial evaluation of novel 8-fluoro Norfloxacin derivatives as potential probes for methicillin and vancomycin-resistant Staphylococcus aureus

A series of novel 8-fluoro Norfloxacin derivatives and the hybrids of its piperazinyl derivatives incorporated with 1,3,5-triazine and pyrimidine were synthesized. All the above compounds were evaluated for their antibacterial activity against Klebsiella pneumoniae, methicillin-resistant Staphylococcus aureus and methicillin & vancomycin-resistant S. aureus. Among all, compounds having Morpholine, N-methyl/phenyl/benzyl/pyrimidinyl piperazines and n-butylamine substitution at C-7 position, have shown increased potency in comparison to norfloxacin and ciprofloxacin.

NOVEL METHOD OF SYNTHESIS OF FLUOROQUINOLONES

The invention relates to a method of preparation of fluoroquinolones of formula (I) from compounds of formula (II): in which R1, R2, R3, R4, R5, R6, R7, and X are as defined in Claim 1.

Microwave assisted amination of quinolone carboxylic acids: An expeditious synthesis of fluoroquinolone antibacterials

A facile amination of quinolone carboxylic acids to fluoroquinolone antibacterials under microwave irradiation is described.

Process for the preparation of quinoline carboxylic acid derivatives

The invention relates to a new process for the preparation of antibacterial compounds of the Formula I STR1 wherein R1 stands for phenyl substituted by 1 or 2 halogen atoms; R2 stands for piperazinyl or 4-methyl-piperazinyl; and pharmaceutically acceptable salts thereof which comprises using a compound of the Formula II STR2 wherein R stands for halogen or an aliphatic acyloxy group containing 2 to 6 carbon atoms or an aromatic acyloxy group containing 7 to 11 carbon atoms and R4 stands for fluorine or chlorine as a starting material.