110548-02-2

Basic information

• Product Name: Levofloxacin Tetrafluoro Impurity 1
• Synonyms: Levofloxacin Tetrafluoro Impurity 1;ethyl (S,Z)-3-((1-hydroxypropan-2-yl)amino)-2-(2,3,4,5-tetrafluorobenzoyl)acrylate;Levofloxacin Impurity 14
• CAS NO: 110548-02-2
• Molecular Formula: C₁₅H₁₅F₄NO₄
• Molecular Weight: 349.28
• Mol File: 110548-02-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 463.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.359±0.06 g/cm3(Predicted)
• PKA: 14.47±0.10(Predicted)
• CAS DataBase Reference: Levofloxacin Tetrafluoro Impurity 1(CAS DataBase Reference)
• NIST Chemistry Reference: Levofloxacin Tetrafluoro Impurity 1(110548-02-2)
• EPA Substance Registry System: Levofloxacin Tetrafluoro Impurity 1(110548-02-2)

Safety Data

• Hazardous Substances Data: 110548-02-2(Hazardous Substances Data)

Usage

Uses

2,3,4,5-Tetrafluoro-α-[[[(1S)-2-hydroxy-1-methylethyl]amino]methylene]-β-oxo-benzenepropanoic Acid Ethyl Ester is used in the synthesis of the drug Levofloxacin (L360000), which is a S-(-) form of Ofloxacin (O245750), an antibiotic used against gram-negative organisms.

Upstream product

• 2749-11-3 (S)-Alaninol 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 122-51-0 orthoformic acid triethyl ester 
• 103995-33-1 3-(2,3,4,5-tetrafluorophenyl)-3-oxo-2-(ethoxymethylene)-propanoic acid ethyl ester 

Downstream Products

• 106939-34-8 ethyl (S)-(-)-9,10-Difluoro-3-Methyl-7-Oxo-2,3-Dihydro-7H-Pyrido[1,2,3-de]-[1,4]Benzoxazine-6-Carboxylate 
• 100986-89-8 levofloxacin Q-acid 
• 100986-85-4 levofloxacin 
• 110548-03-3 (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate 

Relevant articles and documents

Novel ofloxacin derivatives: Synthesis, antimycobacterial and toxicological evaluation

Thirty novel 9-fluoro-2,3-dihydro-8,10-(mono/di-sub)-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acids were synthesized from 2,3,4,5-tetrafluoro benzoic acid and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB), and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from mycobacteria. Among the synthesized compounds, 10-[2-carboxy-5,6-dihydroimidazo[1,2-a]pyrazin-7(8H)-yl]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active compound in vitro with MIC99 of 0.19 μM and 0.09 μM against MTB and MTR-TB, respectively. In the in vivo animal model also the same compound decreased the bacterial load in lung and spleen tissues with 1.91 and 2.91 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 10-[(4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)]-9-fluoro-2,3-dihydro-3-methyl-8-nitro-7-oxo-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid was found to be the most active in the inhibition of the supercoiling activity of DNA gyrase with an IC50 of 10.0 μg/mL. The results demonstrate the potential and importance of developing new oxazino quinolone derivatives against mycobacterial infections.

ANTIMICROBIAL QUINOLONES, THEIR COMPOSITIONS AND USES

Compounds of the following formula (I) are effective antimicrobial agents.