Synthesis and antibacterial activity of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position

Bioorganic & Medicinal Chemistry Letters
2004.0

Abstract

A series of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position were synthesized to obtain potent drugs for the treatment of Gram-positive infections. Some compounds exhibited excellent antibacterial activity, and potent inhibitory activity against bacterial DNA topoisomerase IV. In addition, some of the potent compounds showed reduced inhibitory activity against human DNA topoisomerase II compared with the corresponding noncyclopropane-fused compounds.

Knowledge Graph

Similar Paper

Synthesis and antibacterial activity of novel 6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-4-oxoquinoline-3-carboxylic acids bearing cyclopropane-fused 2-amino-8-azabicyclo[4.3.0]nonan-8-yl substituents at the C-7 position
Bioorganic & Medicinal Chemistry Letters 2004.0
Synthesis and Structure−Activity Relationships of 5-Amino-6-fluoro-1-[(1R,2S)-2-fluorocyclopropan-1-yl]-8-methylquinolonecarboxylic Acid Antibacterials Having Fluorinated 7-[(3R)-3-(1-Aminocyclopropan-1-yl)pyrrolidin-1-yl] Substituents
Journal of Medicinal Chemistry 2003.0
Design, synthesis and biological evaluations of novel 7-[3-(1-aminocycloalkyl)pyrrolidin-1-yl]-6-desfluoro-8-methoxyquinolones with potent antibacterial activity against multi-drug resistant Gram-positive bacteria
Bioorganic & Medicinal Chemistry 2009.0
Synthesis and structure-activity relationships of new 7-[3-(fluoromethyl)piperazinyl]- and -(fluorohomopiperazinyl)quinolone antibacterials
Journal of Medicinal Chemistry 1990.0
Fluorocyclopropyl quinolones. 1. Synthesis and structure-activity relationships of 1-(2-fluorocyclopropyl)-3-pyridonecarboxylic acid antibacterial agents
Journal of Medicinal Chemistry 1993.0
3-Fluoro-2-(4-methylpiperazin-1-yl)-5,12-dihydro-5-oxobenzoxazolo[3,2-a]quinoline-6-carboxylic acid: Synthesis and In vitro cytotoxic activity
Bioorganic & Medicinal Chemistry Letters 1995.0
Novel quinolone derivatives as potent antibacterials
Bioorganic & Medicinal Chemistry Letters 1998.0
Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents
Bioorganic & Medicinal Chemistry 2010.0
Synthesis and antibacterial activity of 1-(substituted pyrrolyl)-7-(substituted amino)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acids
Journal of Medicinal Chemistry 1992.0
Novel 3-fluoro-6-methoxyquinoline derivatives as inhibitors of bacterial DNA gyrase and topoisomerase IV
Bioorganic & Medicinal Chemistry Letters 2017.0