116162-74-4

Basic information

• Product Name: 1-tert-butyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid
• CAS NO: 116162-74-4
• Molecular Formula: C₁₈H₂₂FN₃O₃
• Molecular Weight: 347.384
• Mol File: 116162-74-4.mol

Chemical Properties

• Boiling Point: 553.7°C at 760 mmHg
• Flash Point: 288.7°C
• Density: 1.305g/cm³
• Vapor Pressure: 4.27E-13mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: 1-tert-butyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 1-tert-butyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(116162-74-4)
• EPA Substance Registry System: 1-tert-butyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid(116162-74-4)

Safety Data

• Hazardous Substances Data: 116162-74-4(Hazardous Substances Data)

Usage

Molecular structure

1-tert-butyl-6-fluoro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxylic acid has a complex molecular structure with multiple functional groups.

Classification

It belongs to the quinolone class of antibiotics.

Primary use

The compound is used primarily for its antibacterial properties.

Stability and activity

The tert-butyl group and fluoro substitution contribute to the compound's stability and activity against a wide range of bacteria.

Pharmacokinetic properties

The piperazin-1-yl group enhances the compound's pharmacokinetic properties, increasing its solubility and bioavailability.

Mechanism of action

The compound works by inhibiting DNA gyrase and topoisomerase IV enzymes in bacteria, leading to the disruption of DNA replication and cell death.

Effectiveness

It is an effective agent in the treatment of various bacterial infections, particularly those affecting the respiratory and urinary tracts.

Upstream product

• 110-85-0 piperazine 
• 116163-13-4 6-Fluoro-7-chloro-1-(1,1-dimethylethyl)-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid 
• 367-21-5 3-chloro-4-fluorophenylamine 
• 116163-44-1 1-tert-Butyl-7-chloro-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester 
• 116163-40-7 3-(2,4-dichloro-5-fluorophenyl)-3-oxo-2-(((1,1-dimethylethyl)amino)methylene)propanoic acid etyhyl ester 
• 86483-52-5 2,4-dichloro-alpha(elhoxymethlene)-5-fluoro-beta-oxo-benzene propanoic acid ethyl ester 
• 75073-15-3 ethyl 7-chloro-6-fluoro-4-oxo-1,4-dihydroquinoline 3-carboxylate 
• 70032-30-3 diethyl 2-[(3-chloro-4-fluorophenylamino)methylene]malonate 

Relevant articles and documents

Novel fluoroquinolones: Design, synthesis, and in vivo activity in mice against Mycobacterium tuberculosis H37Rv

Novel 6,8-difluoro-1-alkyl-5-amino-1,4-dihydro-4-oxo-7-{4-substituted piperazin-1-yl}-quinoline-3-carboxylic acids, with the substituents at 4th position of piperazine being -[2(pyridine-4-carbonyl) hydrazono]propyl and -2 [(pyrazine-2-carbonyl) amino] ethyl, were synthesized and evaluated in vivo against Mycobacterium tuberculosis H37Rv in Swiss albino mice. Test compounds exhibited activity comparable to that of sparfloxacin (survival rate, reduction of splenomegaly and reduced tubercular lesions) at a dose of 200 mg/kg.

1-tertiary-alkyl-substituted naphthyridine carboxylic acid antibacterial agents

There are disclosed new naphthyridine- and quinoline-carboxylic acids having a 1-tertiary-alkyl substituent, compositions containing them, and their use in treating bacterial infections in warm-blooded animals. Also disclosed are novel amines and intermediates used in the preparation of the naphthyridine- and quinoline-carboxylic acids.

Fluoronaphthyridines and Quinolones as Antibacterial Agents. 1. Synthesis and Structure-Activity Relationships of New 1-Substituted Derivatives

A series of novel 7-piperazinyl-1-substituted-6-fluoroquinolones and naphthyridines have been prepared and their antibacterial activities evaluated.These derivatives are characterized by having alkyl, alkenyl, arylalkyl, cycloalkyl, and cycloalkenyl groups at the 1-position.As a result of this study, derivatives 7 and 26, which are substituted with tert-butyl groups at N-1, were found to possess excellent in vitro and in vivo potency, particularly against Staphylococcus aureus, comparable to that of norfloxacin (1) or ciprofloxacin (10).Structure-activity relationships of N-1 substituted alkyls and cycloalkyls are also discussed.