86393-33-1

Usage

Uses

Used in Pharmaceutical Industry:
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is used as an intermediate in the synthesis of Ciprofloxacin, a fluorinated quinolone antibacterial. It plays a crucial role in the production process of this widely used antibiotic medication.
Used in Metabolism Studies:
As a metabolite of Ciprofloxacin, 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid is utilized in research and studies to understand the metabolic pathways and pharmacokinetics of the antibiotic, contributing to the optimization of its therapeutic use and potential improvements in drug design.
Used in Quality Control:
7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic Acid (Ciprofloxacin EP Impurity A) is recognized as a metabolite of Ciprofloxacin and is used in quality control processes to ensure the purity and efficacy of the final antibiotic product. This helps maintain the safety and effectiveness of Ciprofloxacin as a fluorinated quinolone antibacterial.

InChI:InChI=1/C13H9ClFNO3/c14-9-4-11-7(3-10(9)15)12(17)8(13(18)19)5-16(11)6-1-2-6/h3-6H,1-2H2,(H,18,19)/p-1

Upstream product

• 86483-54-7 ethyl 1-cyclopropyl-7-chloro-6-fluoro-1,4-dihydro-4-oxo-3-quinoline-carboxylate 
• 122-51-0 orthoformic acid triethyl ester 
• 765-30-0 Cyclopropylamine 
• 104600-30-8 ethyl 2-(2,4-dichloro-5-fluoro-benzoyl)-3-cyclopropylamino-acrylate 
• 1310-58-3 potassium hydroxide 
• 103318-78-1 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid nitrile 
• 7664-93-9 sulfuric acid 
• 16173-58-3 N,N-dimethylaminoacrylic acid ethyl ester 
• 86393-34-2 2,4-dichloro-5-fluorobenzoyl chloride 
• 93107-08-5 ciprofloxacin hydrochloride 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 70032-30-3 diethyl 2-[(3-chloro-4-fluorophenylamino)methylene]malonate 
• 75073-15-3 ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate 
• 104600-41-1 3-(2,4-dichloro-5-fluorophenyl)-3-oxo-2-ethoxymethylenepropanoic acid ethyl ester 

Downstream Products

• 85721-33-1 ciprofloxacin 
• 93106-60-6 enrofloxacin 
• 133210-96-5 1-cyclopropyl-7-chloro-6-piperazinyl-4-oxo-1,2-dihydroquinoline-3-carboxylic acid 
• 104599-90-8 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 
• 526204-10-4 7-chloro-1-cyclopropyl-4-oxo-6-piperazin-1-yl-1,4-dihydro-quinoline-3-carboxylic acid; hydrochloride 
• 93107-08-5 ciprofloxacin hydrochloride 
• 528851-85-6 6-[(2-aminoethyl)amino]-7-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 528851-30-1 6-[(2-aminoethyl)amino]-7-chloro-1-cyclopropyl-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid hydrochloride 
• 528851-31-2 2-((3-carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)amino)ethan-1-aminium chloride 
• 1187831-29-3 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-chloro-3-[N-(benzalhydrazinyl)-carbonyl]quinoline 
• 1187831-30-6 C₂₁H₁₇ClFN₃O₃ 
• 1187831-31-7 C₂₁H₁₇ClFN₃O₄ 
• 1187831-32-8 C₂₀H₁₄ClF₂N₃O₂ 
• 1187831-33-9 C₂₀H₁₅ClFN₃O₃ 

Relevant academic research and scientific papers

An operational transformation of 3-carboxy-4-quinolones into 3-nitro-4-quinolones via ipso-nitration using polysaccharide supported copper nanoparticles: Synthesis of 3-tetrazolyl bioisosteres of 3-carboxy-4-quinolones as antibacterial agents

Chitosan supported Cu nano-particles have been synthesized, and utilized for the synthesis of 3-nitro-4-quinolones from 3-carboxy-4-quinolones via ipso nitration. The synthesized 3-nitro derivatives of 4-quinolones were successfully converted into their 3-tetrazolyl bioisosteres which showed increased antibacterial activity as compared to the standard ciprofloxacin.

ANTIVIRAL AND ANTIMICROBIAL COMPOUNDS

Disclosed are guanidine and biguanidine derivatives which have anti-viral and antibacterial activity. Also disclosed are pharmaceutical compositions containing such compounds as an active ingredient, and anti-viral and anti-bacterial methods utilizing such compounds. Methods of treating infections using the guanidine and biguanidine derivatives are also disclosed.

Synthesis, characterization and biological studies of some homodinuclear complexes of zinc with second-generation quinolone drug and neutral bidentate ligands

The novel homodinuclear zinc(II) complexes with the quinolone antibacterial drugs ciprofloxacine and neutral bidentate ligands have been synthesized and characterized by elemental analysis, TG analyses and various spectroscopic techniques. The metal ion exhibits octahedral geometry with two water molecule in the inner sphere cavity environment. The interaction of complexes with DNA was determined using absorption titration, viscosity measurements and electrophoresis technique. The intrinsic binding constants (Kb) of complexes were determined, which were ranging from 1.0 × 104 to 3.5 × 104 per mole. Suggesting that complexes bind more strongly to DNA. Effect on viscosity has also been checked to authenticate the binding of metal complexes with DNA. An antimicrobial activity of all the ligands and metal complexes has been examined by minimum inhibitory concentration method (MIC).

Synthesis of amide derivatives of quinolone and their antimicrobial studies

A series of 1 -cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[chloro/1 -piperazinyl/4-methyl-1-piperazinyl/4-ethyl-1-piperazinyl/ 4-hydroxyethyl-1- piperazinyl/imidazolyl/morpholinyl]-3[N-(substituted phenyl amino) carbonyl]quinoline 5-11a-j have been prepared by using substituted arylamine at C-3 position and 1-piperazine/4-methyl-1-piperazine/4-ethyl-1-piperazine/4- hydroxyethyl-1-piperazine/imidazole/morpholine at C-7 position of newly synthesized quinolone 3. Biological profile like antibacterial activity against four different strain viz. S. aureus and B. subtilis (gram-positive bacteria) and E. coli and P. aeruginosa (gram-negative bacteria) and C. albicans (fungi) by cup plate method have been studied.

Compounds with antibacterial and antiparasitic properties

There are provided novel compounds which have both antibacterial and antiparasitic properties, thereby reducing the need for using several compounds in combined antibacterial and antiparasitic treatment of livestock. The present novel compounds are especially well suited for treatment of coccidiosis, and they are represented by general formula (I) wherein R1-R6, X and A are as defined in the specification.

An expeditious synthesis of quinolone antibacterials

A facile and rapid synthesis of ciprofloxacin under microwave irradiation is described. The product ciprofloxacin was isolated and the impurity was characterized as the product of substitution of fluorine instead of chlorine in acid 1. Similarly norfloxacin was synthesized.

Process for preparing quinolone- and naphthyridone- carboxylic acids and esters thereof

An improved process for preparing quinolone- and naphthyridonecarboxylic acids and esters thereof from benzoyl chlorides and nicotinoyl chlorides, respectively, in which the reaction carried out in the presence of a non-polar to slightly polar solvent without separation of intermediaries that form during the process.

Electrochemical studies of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(N- piperazinyl)-4-oxo-3-quinoline carboxylic acid and its synthetic precursors

Electrochemical studies of 1-cyclopropyl-6-fluoro-1,4-dihydro-7-(N- piperazinyl)-4-oxo-3-quinoline carboxylic acid 5 and its synthetic precursors, viz., 2, 4-dichloro-5-fluoroacetophenone 1, 3-cyclopropylamino-2- (2,4-dichloro-5-fluorobenzoyl)acrylic acid methyl ester 2, 7-chloro-1- cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid methyl ester 3 and 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3- carboxylic acid 4 are reported. Plausible electrochemical mechanism for the reduction of the series of compounds is suggested based on cyclic voltammetry, coulometry and spectral studies. The role of resonance isomerism aided by intramolecular hydrogen bonding and aromaticity, in the electrochemistry of compounds 2-5, is discussed. The acid-base equilibria of the compounds are revisited based on PCMODEL MMX Molecular Energy Minimisation Software and cyclic voltammetry. An excellent electroanalytical method in differential pulse polarography for the quantitative analysis of the drug 5 and its synthetic precursors 14 is developed.

Process for the preparation of quinolonecarboxylic acid esters

A process for the preparation of quinolone-carboxylic acid esters of the formulae I and II STR1 in which A represents nitrogen or =C--R4, R4 represents hydrogen, fluorine, chlorine, nitro or methyl, B represents halogen, nitro, alkoxy, alkylsulphonyloxy or the radical STR2 and B additionally represents STR3 if R1 does not denote cyclopropyl, and R5 represents a branched or unbranched alkyl group which has 1 to 4 carbon atoms and which can optionally be substituted by a hydroxyl or methoxy group, R6 represents hydrogen, methyl or phenyl, R7 represents hydrogen or methyl, R8 represents dialkylamino having 1 or 2 carbon atoms in the alkyl group or dialkylaminomethyl having 1 or 2 carbon atoms in the alkyl group, or aminomethyl R1 represents hydrogen, optionally substituted alkyl having 1 to 3 carbon atoms, optionally substituted cycloalkyl, 2-fluoroethyl, vinyl, methoxy or 4-fluorophenyl, R2 represents optionally substituted alkyl having 1 to 6 carbon atoms and also cyclohexyl and benzyl, R3 represents hydrogen, methyl or ethyl, and Z represents oxygen, nitrogen which is substituted by methyl or phenyl, and =CH2, characterized in that quinolonecarboxylic acids of the formulae III and IV STR4 in which A, B, Z, R1 and R3 have the meanings indicated above, are reacted with chloroformic acid esters of the formula V in which R2 has the meaning indicated above.

7-(substituted)piperazinyl-1-ethyl-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids

7-(substituted)piperazinyl-1-ethyl-6-fluoro-4-oxo-3-quinolinecarboxylic acids, the pharmacologically acceptable salts thereof, compositions containing them, processes and intermediates for producing them, and methods of using them to treat bacterial infections in warm-blooded animals.