108461-05-8

Usage

Chemical class

Quinolone antibiotics

Use

Treat a variety of bacterial infections

Structural components

Cyclopropyl group
Fluoro group
Dihydroquinoline ring

Potency

Potent antibacterial agent

Functional group

Carboxylic acid group

Properties affected by carboxylic acid group

Solubility in biological systems
Reactivity in biological systems

Upstream product

• 93107-30-3 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid 
• 17783-50-5 8-methyl-3,8-diazabicyclo<3.2.1>octane hydrochloride 
• 6674-22-2 1,8-diazabicyclo[5.4.0]undec-7-ene 

Relevant academic research and scientific papers

Substituted bridged diazabicycloalkyl quinolone carboxylic acids

Antibacterial compounds have the formula STR1 wherein R1 is hydrogen, a pharmaceutically acceptable cation, or alkyl; A is CH, CF, CCl or N; Y is alkyl, haloalkyl, cyclopropyl, vinyl, methoxy, N-methylamino, p-fluorophenyl, p-hydroxyphenyl or p

Synthesis and structure-activity relationships of 7- diazabicycloalkylquinolones, including danofloxacin, a new quinolone antibacterial agent for veterinary medicine

A series of novel 6-fluoro-7-diazabicycloalkylquinolonecarboxylic acids substituted with various C8 (H, F, Cl, N) and N1 (ethyl, cyclopropyl, vinyl, 2-fluoroethyl, 4-fluorophenyl, 2,4-difluorophenyl) substituents, as well as, 9-fluoro-10-diazabicycloalkylpyridobenzoxazinecarboxylic acids, were prepared and evaluated for antibacterial activity against a range of important veterinary pathogenic bacteria. The diazabicycloalkyl side chains investigated at the 7-position (benzoxazine 10-position) include (1S,4S)-5- methyl-2,5-diazabicyclo[2.2.1]heptane (2), (1S,4S)-2,5- diazabicyclo[2.2.1]heptane (3), (1R,4R)-5-methyl-2,5- diazabicyclo[2.2.1]heptane (4), 8-methyl-3,8-diazabicyclo[3.2.1]octane (5), 9-methyl-3,9-diazabicyclo[4.2.1]nonane (6), 1,4-diazabicyclo[3.2.2]nonane (7), 1,4-diazabicyclo[3.3.1]nonane (8), and 9-methyl-3,9- diazabicyclo[3.3.1]nonane (9). Among these side chains, in vitro potency was not highly variable; other properties therefore proved more critical to the selection of possible development candidates. However, the relative potencies observed for several of these compounds in mouse, swine, and cattle infection models correlated well with those seen in vitro. A combination of the N1 cyclopropyl group and the C7 (1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]hept-2- yl appendage conferred the best overall antibacterial, physiochemical, and pharmacodynamic properties. Hence, danofloxacin (Advocin, 2c) (originally CP- 76,136, 1-cyclopropyl-6-fluoro-7-[(1S,4S)-5-methyl-2,5- diazabicyclo[2.2.1]hept-2-yl]-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid) was selected as a candidate for development as a therapeutic antibacterial agent for veterinary medicine.

Anti-bacterial substituted bridged-diazabicycloalkyl quinolone carboxylic acids

Antibacterial compounds have the formula STR1 wherein R1 is hydrogen, a pharmaceutically acceptable cation, or alkyl; A is CH, CF, CCl or N; Y is alkyl, haloalkyl, cyclopropyl, vinyl, methoxy, N-methylamino, p-fluorophenyl, p-hydroxyphenyl or p

Substituted bridged-diazabicycloalkyl quinolone carboxylic acids and anti-bacterial use thereof

Antibacterial compounds have the formula STR1 wherein R1 is hydrogen, a pharmaceutically aceptable cation, or alkyl; A is CH, CF, CCl or N; Y is alkyl, haloalkyl, cyclopropyl, vinyl, methoxy, N-methylamino, p-fluorophenyl, p-hydroxyphenyl or p-