| Identification | More | [Name]
6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid | [CAS]
112984-60-8 | [Synonyms]
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-FLUORO-1-METHYL-4-OXO-7-PIPERAZIN-1-YL-4H-2-THIA-8B-AZA-CYCLOBUTA[A] NAPHTHALENE-3-CARBOXYLIC ACID
PRULIFLOXACIN INTERMEDIATE 3
6-Fluoro-1-Methyl-4-Oxo-7-(1-Piperazinyl)-4H-(1,3)-Thiazeto(3,2-Alpha)Quinoline-3-Carboxylic Acid
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPRAZINYL)-4H-(1,3)-THIAZETO(3,2-A)QUINOLINE-3-CAR
1H,4H-[1,3]Thiazeto[3,2-a]quinoline-3-carboxylic acid, 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPRAZINYL)-1H,4H-(1,3)THIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)-thiazeto(3,2-a)quinoline-3-carboxylic acid cas:(intermediate of prulifloxacin)
6-FLUORO-1-METHYL-4-OXO-7-(1-PIPERAZINYL)-4H-(1,3)-HIAZETO(3,2-A)QUINOLINE-3-CARBOXYLIC ACID
6-FLUORO-7-PIPERAZINE-1-METHYL-4-OXY-[1,3]THIOAZACYCLIC[3,2-A]-QUINOLINE-3-CARBOXYLIC ACID
NM 394
6-Fluoro-1-methyl-7-(1-piperazinyl)-4-oxo-4H-(1,3)thiazeto(3,2-a)quinoline-3-carboxylic acid
ulifloxacin
Prulifloxacin Intermediate PL-11
6-Fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-(1,3)-thiazeto | [EINECS(EC#)]
601-220-5 | [Molecular Formula]
C16H16FN3O3S | [MDL Number]
MFCD00882994 | [Molecular Weight]
349.38 | [MOL File]
112984-60-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
215-218 °C (decomp) | [Boiling point ]
577.0±50.0 °C(Predicted) | [density ]
1.58±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Sparingly), Methanol (Slightly) | [form ]
Solid | [pka]
5.85±0.40(Predicted) | [color ]
Pale Yellow to Yellow | [InChI]
1S/C16H16FN3O3S/c1-8-20-11-7-12(19-4-2-18-3-5-19)10(17)6-9(11)14(21)13(16(22)23)15(20)24-8/h6-8,18H,2-5H2,1H3,(H,22,23) | [InChIKey]
SUXQDLLXIBLQHW-UHFFFAOYSA-N | [SMILES]
Fc1cc2c(cc1N4CCNCC4)N3C(SC3=C(C2=O)C(=O)O)C | [CAS DataBase Reference]
112984-60-8(CAS DataBase Reference) |
| Safety Data | Back Directory | [WGK Germany ]
WGK 3 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Lact.
Skin Irrit. 2
STOT RE 2 |
| Hazard Information | Back Directory | [Chemical Properties]
Yellow Solid | [Uses]
A labelled metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia. | [Uses]
A metabolite of Prulifloxacin (P838885). Ulifloxacin is a new quinolone antibiotic and it is effective against pneumonia. | [Definition]
ChEBI: Ulifloxacin is a member of quinolines. | [Biological Activity]
Ulifloxacin is an orally availablebroad-spectrum fluoroquinolone antibacterial agent. Ulifloxacin is an active metabolite of Prulifloxacin. It potently inhibits bacterial DNA gyrase and topoisomerase IV. | [Synthesis]
The general procedure for the synthesis of 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazolo[3,2-a]quinoline-3-carboxylic acid from ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-1,4-dihydro-[1,3]thiazolo[3,2-a]quinoline-3-carboxylate was as follows:
1. ethyl 6-fluoro-1-methyl-4-oxo-7-(1-piperazinyl)-4H-[1,3]thiazolo[3,2-a]quinoline-3-carboxylate (100 g, 0.265 mol) was dissolved in water (600 ml) at 25-30 °C with stirring.
2. potassium hydroxide solution (50 g of potassium hydroxide flakes dissolved in 200 ml of water) was slowly added to this solution.
3. the reaction mixture is heated to 80-85°C and stirred at this temperature for 1 hour.
4. After completion of the reaction, the reaction mixture was cooled down to 25-30 °C. The reaction mixture was then cooled down to 25-30 °C.
5. The pH of the reaction mixture was adjusted to 6.5-7.0 using a 1:1 aqueous solution of acetic acid.
6. The reaction mixture was stirred at room temperature for 1 hour to allow the product to fully precipitate.
7. The precipitated solid was collected by filtration and washed with distilled water (2 x 100 mL).
8. The solid was slurried in methanol (300 ml) at 25-30 °C for 1 h. The reaction mixture was stirred for 1 h at room temperature.
9. After filtration, the solid was washed with methanol (2 x 50 ml).
10. The product was dried under vacuum at 70-75 °C to afford 6-fluoro-1-methyl-4-oxo-7-(piperazin-1-yl)-1,4-dihydro-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid (90 g, 97% yield, 96% HPLC purity). | [References]
[1] Patent: WO2012/1357, 2012, A1. Location in patent: Page/Page column 22
[2] Patent: CN103113392, 2016, B. Location in patent: Paragraph 0024; 0037; 0038; 0039
[3] Patent: CN107383069, 2017, A. Location in patent: Paragraph 0063; 0064
[4] Journal of Medicinal Chemistry, 1992, vol. 35, # 25, p. 4727 - 4738
[5] Patent: WO2009/93268, 2009, A1. Location in patent: Page/Page column 15 |
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