110548-03-3

Basic information

• Product Name: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate
• Synonyms: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate
• CAS NO: 110548-03-3
• Molecular Weight: 329.276
• Mol File: 110548-03-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate(110548-03-3)
• EPA Substance Registry System: (-)-ethyl 1,4-dihydro-1-<1(S)-(hydroxymethyl)ethyl>-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate(110548-03-3)

Safety Data

• Hazardous Substances Data: 110548-03-3(Hazardous Substances Data)

Usage

Uses

6,7,8-Trifluoro-1,4-dihydro-1-[(1S)-2-hydroxy-1-methylethyl]-4-oxo-3-quinolinecarboxylic 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

• 110548-02-2 (+)-ethyl 2-<<<(S)-1-hydroxyprop-2-yl>amino>methylene>-3-oxo-3-(2,3,4,5-tetrafluorophenyl)propionate 
• 188058-77-7 (-)-ethyl 1,4-dihydro-1-[1(S)-(acetoxymethyl)ethyl]-4-oxo-6,7,8-trifluoroquinoline-3-carboxylate 
• 94695-48-4 2,3,4,5-tetrafluorobenzoyl chloride 
• 188058-81-3 (+)-ethyl 2-(2,3,4,5-tetrafluorobenzoyl)-3-[(1-acetoxyprop-2(S)-yl)amino]acrylate 
• 94695-50-8 ethyl 3-(2,3,4,5-tetrafkuorophenyl)-3-oxopropanoate 
• 103995-33-1 3-(2,3,4,5-tetrafluorophenyl)-3-oxo-2-(ethoxymethylene)-propanoic acid ethyl ester 

Downstream Products

• 100986-85-4 levofloxacin 
• 100986-89-8 levofloxacin Q-acid 

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.

Chiral DNA gyrase inhibitors. 2. Asymmetric synthesis and biological activity of the enantiomers of 9-fluoro-3-methyl-10-(4-methyl-1-piperazinyl)-7-oxo-2,3-dihydro-7H-py ido[1,2,3,-de]-1,4-benzoxazine-6-carboxylic acid (ofloxacin)

A short and efficient synthesis, starting with (R)- and (S)-alaninol, of the two optical antipodes of the quinolone antimicrobial agent ofloxacin has been devised. Testing in vitro of the products against a range of bacteria and in an assay system incorporating purified DNA gyrase from different bacterial species demonstrates that the S-(-) enantiomer is substantially the more active.