127625-17-6

Basic information

• Product Name: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• Synonyms: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate
• CAS NO: 127625-17-6
• Molecular Formula: C₁₅H₁₃ClN₂O₅
• Molecular Weight: 337
• Mol File: 127625-17-6.mol

Chemical Properties

• Melting Point: >280 °C
• Boiling Point: 518.5±50.0 °C(Predicted)
• Appearance: /
• Density: 1.531±0.06 g/cm3(Predicted)
• PKA: -8.35±0.40(Predicted)
• CAS DataBase Reference: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate(127625-17-6)
• EPA Substance Registry System: Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate(127625-17-6)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 127625-17-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate is used as an active ingredient in pharmaceutical formulations for its antimicrobial properties. It is particularly effective in treating bacterial infections caused by Gram-negative bacteria due to its ability to inhibit bacterial DNA replication and protein synthesis.
Used in Medicine:
Ethyl 7-chloro-1-cyclopropyl-6-nitro-4-oxo-1,4-dihydro-3-quinolinecarboxylate is used as an antibiotic for the treatment of various bacterial infections. Its complex molecular structure, including the cyclopropyl ring, nitro group, and quinolinecarboxylate moiety, contributes to its therapeutic effects, making it a valuable compound in the medical field.

Upstream product

• 148926-95-8 ethyl ester of 3-cyclopropylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid 
• 713-28-0 2,4-dichloro-5-nitro benzoyl chloride 
• 174312-93-7 ethyl ester of (5-nitro-2,4-dichlorobenzoyl)acetic acid 
• 148926-94-7 ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid 
• 174312-92-6 diethyl 2,4-dichloro-5-nitrobenzoylmalonate 
• 924-99-2 ethyl 3-(dimethylamino)acrylate 
• 19861-62-2 2,4-dichloro-5-nitrobenzoic acid 

Downstream Products

• 1026479-59-3 1-cyclopropyl-7-[4-(2-methoxy-phenyl)-piperazin-1-yl]-6-nitro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1025804-75-4 1-cyclopropyl-6-nitro-4-oxo-7-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1027274-26-5 6-amino-1-cyclopropyl-7-[4-(2-methoxy-phenyl)-piperazin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 1027375-42-3 6-amino-1-cyclopropyl-4-oxo-7-[4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 

Relevant articles and documents

Advantageous Use of Ionic Liquids for the Synthesis of Pharmaceutically Relevant Quinolones

The advantageous use of ionic liquids (ILs) as alternatives to common DMF as solvent in the Grohe cycloaracylation for the synthesis of pharmaceutically relevant quinolones is reported. ILs showed in many cases shorter reaction times and higher yields, complete conversions of the reactants and easy work-up procedures compared with DMF. Of the ILs screened, tributylmethylammonium methanesulfonate ([TBMA][MsO]) was selected as the most suitable for further studies. Interestingly, a wide substrate scope was observed and the IL was recycled by a green process. A further step forward in the use of [TBMA][MsO] for quinolone synthesis was the preparation by a one-pot/three-step procedure of the representative 3-carboxy-4-quinolone acid 16, which was obtained in high yield in a short time. The greener properties of ILs in comparison with DMF and their non-volatility appoint this method as a potentially efficient and alternative approach to the industrial production of quinolones.

Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids

Various 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids were synthesized from 2,4-dichlorobenzoic acid by six step synthesis. The compounds were evaluated for antimycobacterial in vitro and in vivo against My

6-Aminoquinolones: A new class of quinolone antibacterials?

A series of quinolone- and 1,8-naphthyridone-3-carboxylic acids, designed by previous QSAR studies and characterized by an amino group at the C-6 position instead of the usual fluorine atom, were synthesized for the first time and evaluated for in vitro antibacterial activity. All of the synthesized compounds maintain good activity against Gram-negative bacteria (Pseudomonas aeruginosa excluded), and those compounds having a thiomorpholine group as the C-7 substituent also have good activity against Gram-positive bacteria. Some aspects of structure activity relationships associated with the C-1, C-5, C-7, and C-8 substituents are also discussed. Derivatives 18g and 38g displayed the best activity with geometric mean MICs of 0.45 and 0.66-0.76 μg/mL against Gram-negative and Gram-positive bacteria, respectively. This antimicrobial activity reflects their ability to inhibit bacterial DNA-gyrase. The results of this study show that, while the C-6 fluorine is still the preferred substituent, good activity can still be obtained by replacing it with an amino group.

Imidazo- and triazoloquinolones as antibacterial agents. Synthesis and structure-activity relationships

4,5-Disubstituted 6-cyclopropyl-6,9-dihydro-9-oxo-1H-imidazo- (30-32) and triazolo[4,5-f]quinoline-8-carboxylic acids (33-35) were synthesized starting from 5,6-diaminoquinolones 25. The imidazoquinolones 30-32 were equal or superior to the corresponding triazoloquinolone analogues 33-35 in in vitro antibacterial activity. As for the C-5 substituents, a fluorine atom was the most favorable of the three groups, H, F, and Cl. Among the compounds prepared, 4-(cyclic amino)-5-fluoro-imidazoquinolones 31a-d showed potent and well-balanced antibacterial activity against both gram-positive and gram- negative bacteria. Structure-activity relationships for the C-4 substituents (cyclic amino groups) were also examined in detail.