107884-23-1

Basic information

• Product Name: 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Methyl ester
• Synonyms: 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Methyl ester;methyl 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(piperazin-1-yl)quinoline-3-carboxylate
• CAS NO: 107884-23-1
• Molecular Formula: C₁₈H₂₀FN₃O₃
• Molecular Weight: 345.3681032
• Mol File: 107884-23-1.mol
• Article Data: 15

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Methyl ester(107884-23-1)
• EPA Substance Registry System: 3-Quinolinecarboxylic acid, 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-, Methyl ester(107884-23-1)

Safety Data

• Hazardous Substances Data: 107884-23-1(Hazardous Substances Data)

Upstream product

• 85721-33-1 ciprofloxacin 
• 93594-48-0 7-[4-tert-butoxycarbonyl-piperazin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid 
• 1427036-08-5 methyl 1-cyclopropyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylate 2,2,2-trifluoroacetate salt 
• 186581-53-3 diazomethane 
• 952741-81-0 C₁₃H₁₁F₃O₄ 
• 110-85-0 piperazine 
• 127371-54-4 methyl 1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate 
• 67-56-1 methanol 

Downstream Products

• 85721-33-1 ciprofloxacin 
• 620170-31-2 1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-(4-(4-methoxybenzoyl)piperazin-1-yl)quinoline-3-carboxylic acid 

Relevant articles and documents

Synthesis of citrate-ciprofloxacin conjugates

Two regioisomeric citrate-functionalized ciprofloxacin conjugates have been synthesized and their antimicrobial activities against a panel of clinically-relevant bacteria have been determined. Cellular uptake mechanisms were investigated using wild-type and ompF deletion strains of Escherichia coli K-12.

Amphiphilic nebramine-based hybrids Rescue legacy antibiotics from intrinsic resistance in multidrug-resistant Gram-negative bacilli

The inability to discover novel class of antibacterial agents, especially against Gram-negative bacteria (GNB), compel us to consider a broader non-conventional approach to treat infections caused by multidrug-resistant (MDR)bacteria. One such approach is

Toward Catalytic Antibiotics: Redesign of Fluoroquinolones to Catalytically Fragment Chromosomal DNA

A library of ciprofloxacin-nuclease conjugates was designed and synthesized to investigate their potential as catalytic antibiotics. The Cu(II) complexes of the new designer compounds (i) showed excellent in vitro hydrolytic and oxidative DNase activity, (ii) showed good antibacterial activity against both Gram-negative and Gram-positive bacteria, and (iii) proved to be highly potent bacterial DNA gyrase inhibitors via a mechanism that involves stabilization of the fluoroquinolone-topoisomerase-DNA ternary complex. Furthermore, the Cu(II) complexes of two of the new designer compounds were shown to fragment supercoiled plasmid DNA into linear DNA in the presence of DNA gyrase, demonstrating a proof of concept in vitro. These ciprofloxacin-nuclease conjugates can therefore serve as models with which to develop next-generation, in vivo functioning catalytic antimicrobials.

Phosphate-based self-immolative linkers for the delivery of amine-containing drugs

Amine-containing drugs often show poor pharmacological properties, but these disadvan-tages can be overcome by using a prodrug approach involving self-immolative linkers. Accordingly, we designed L-lactate linkers as ideal candidates for amine delivery. Furthermore, we designed linkers bearing two different cargos (aniline and phenol) for preferential amine cargo release within 15 min. Since the linkers carrying secondary amine cargo showed high stability at physiological pH, we used our strategy to prepare phosphate-based prodrugs of the antibiotic Ciprofloxacin. Therefore, our study will facilitate the rational design of new and more effective drug delivery systems for amine-containing drugs.