93969-13-2

Basic information

• Product Name: 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester
• Synonyms: 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester;6,7,8-trifluoro-1-(2-fluoroethyl)-4-keto-quinoline-3-carboxylic acid ethyl ester;6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxo-3-quinolinecarboxylic acid ethyl ester;ethyl 6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxo-quinoline-3-carboxylate;ethyl 6,7,8-trifluoro-1-(2-fluoroethyl)-4-oxoquinoline-3-carboxylate
• CAS NO: 93969-13-2
• Molecular Formula: C14H11F4NO3
• Molecular Weight: 317.24
• Mol File: 93969-13-2.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester(93969-13-2)
• EPA Substance Registry System: 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester(93969-13-2)

Safety Data

• Hazardous Substances Data: 93969-13-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester is used as a key intermediate in the synthesis of fluoroquinolone carboxylic acids for the development of new antimicrobial agents. These fluoroquinolones possess broad-spectrum activity against both Gram-positive and Gram-negative bacteria, making them valuable in treating various infections.
Used in Chemical Research:
In the field of chemical research, 6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester serves as a versatile building block for the creation of novel fluorinated quinoline derivatives. These derivatives can be explored for their potential applications in medicinal chemistry, materials science, and other areas of research.
Used in Synthesis of Fluoro(quinolone)carboxylic Acids:
6,7,8-Trifluoro-1-(2-fluoroethyl)-4-oxo-1,4-dihydroquinoline-3-carboxylic acid ethyl ester is used as a starting material in the preparation of fluoroquinolone carboxylic acids via amination of alkyl fluoro(haloquinolone)carboxylates with amines. This synthetic route allows for the introduction of various amine functionalities, leading to a diverse range of fluoroquinolone derivatives with potential applications in different industries.

Upstream product

• 383-50-6 2-fluoroethyl tosylate 
• 584-08-7 potassium carbonate 
• 79660-46-1 ethyl 6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 113220-16-9 ethyl 3-(2-fluoroethylamino)-2-(2,3,4, 5-tetrafluorobenzoyl) acrylate 

Relevant articles and documents

PROCESSES FOR PREPARING QUINOLONECARBOXYLATE DERIVATIVES

The present invention provides a process for preparing quinolonecarboxylate derivatives under a mild condition in high yield, so as to be favorably applied to a large-scale mass production thereof.

1-Substituted 7--1-pyrrolidinyl>-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acids. New Quantitative Structure-Activity Relationships at N1 for the Quinolone Antibacterials

A series of 18 1-substituted 7--1-pyrrolidinyl>-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (N1 analogues of CI-934) was synthesized and evaluated for antibacterial activity and DNA-gyrase inhibition.Correlations between the inhibition of DNA gyrase and antibacterial potency were established.A quantitative structure-activity relationship (QSAR) was derived by using the antibacterial potency of each of 11 strains of bacteria and the Gram-negative mean.The equations indicated that antibacterial potency was strongly dependent on STERIMOL length and width and the level of unsaturation of the N1 substituent.Some strains also showed a dependence on the presence of heteroatoms (O, N, S) in the N1 group.No significant correlations between gyrase inhibition and correlations of these parameters were found.These QSAR results are discussed in conjunction with the conformational analyses from molecular modeling studies.The substituent that most enhanced the activity of the quinolone in all regards was the cyclopropyl group.This analogue, 1-cyclopropyl-7--1-pyrrolidinyl>-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid (PD 117558), demonstrated outstanding broad spectrum activity both in vitro and in vivo when compared to relevant standards.