99734-97-1

Usage

Chemical class

Fluoroquinolone antibiotics

Cyclopropyl group

A three-carbon ring structure attached to the compound

Pyrrolidinyl group

A five-carbon ring structure with one nitrogen atom

Ethylamino group

An ethyl group attached to an amine group

Fluorine atoms

Two fluorine atoms present in the molecule

Quinolone core structure

The central structure of the compound

Target enzyme

DNA gyrase

Mechanism of action

Inhibition of bacterial DNA replication and transcription

Effective against

A wide range of gram-negative and gram-positive bacteria

Treatment of infections

Respiratory, urinary tract, and skin infections

Prescription

Often prescribed under various brand names and formulations by healthcare professionals

Upstream product

• 94242-51-0 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester 
• 103054-56-4 methyl 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate 
• 91187-83-6 3-((N-ethylamino)methyl)pyrrolidine 
• 94695-52-0 1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinolin-3-carboxylic acid 
• 94695-48-4 2,3,4,5-tetrafluorobenzoyl chloride 
• 94695-51-9 α-<(cyclopropylamino)methylene>-2,3,4,5-tetrafluoro-β-oxobenzenepropanoate 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 1201-31-6 2,3,4,5-tetrafluorobenzoic acid 

Relevant academic research and scientific papers

Antibacterial agents

Novel quinoline-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

Process for quinoline-3-carboxylic acid antibacterial agents

An improved process for the preparation of 7-substituted amino-1-alkyl- or cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids is described where tetrafluorobenzoyl chloride is converted in three operations via 1-alkyl or 1-cycloalkyl-1

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.

Quinolone Antibacterial Agents. Synthesis and Structure-Activity Relationships of 8-Substituted Quinoline-3-carboxylic Acids and 1,8-Naphthyridine-3-carboxylic Acids

A series of 7,8-disubstituted 1-cyclopropyl-6-fluoroquinoline-3-carboxylic acids, 7-substituted 1-cyclopropyl-6-fluoro-1,8-naphthyridine-3-carboxylic acids, and 10-substituted 9-fluoropyridobenzoxazine-6-carboxylic acids has been prepared and evaluated for antibacterial activity.The side chains examined at the 7-position (benzoxazine 10-position) included piperazinyl (g), 3-aminopyrrolidinyl (a), 3-(aminomethyl)pyrrolidinyl (b), and alkylated 3-(aminomethyl)pyrrolidinyl (c-f).Variations ta C-8 of the quinolone ring system included hydrogen, nitro, amino, fluorine and chlorine.The relative enhancement of in vitro activities by the side chains on the 8-hydrogen quinolone and 1,8-naphthyridine against Gram-negative organisms was a > b > g > c-f.The activity imparted to the substituted quinolone nucleus by the 8-substituent was in the order F > Cl > naphthyridine > H > benzoxazine > NH2 > NO2.These trends were retained in vivo.

Antibacterial agents

Novel naphthyridine-, quinoline- and benzoxazine-carboxylic acids as antibacterial agents are described as well as methods for their manufacture, formulation, and use in treating bacterial infections including the description of certain novel intermediates used in the manufacture of the antibacterial agents.

Process for quinoline-3-carboxylic acid antibacterial agents

An improved process for the preparation of 7-substituted amino-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids is described where an alkyl ester of a 6,7,8-trifluoro precursor is converted to a trialkylsilyl ester which fluorine at C7 is directly displaced to the desired product.