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CAS No. : | 127294-70-6 | MDL No. : | MFCD00864925 |
Formula : | C20H24FN3O4 | Boiling Point : | 608.3°C at 760 mmHg |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 389.42 g/mol | Pubchem ID : | 65958 |
Synonyms : |
1. Balofloxacin |
Num. heavy atoms : | 28 |
Num. arom. heavy atoms : | 10 |
Fraction Csp3 : | 0.5 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 107.44 |
TPSA : | 83.8 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -8.26 cm/s |
Log Po/w (iLOGP) : | 2.73 |
Log Po/w (XLOGP3) : | 0.58 |
Log Po/w (WLOGP) : | 2.35 |
Log Po/w (MLOGP) : | 1.44 |
Log Po/w (SILICOS-IT) : | 2.21 |
Consensus Log Po/w : | 1.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.55 |
Solubility : | 1.09 mg/ml ; 0.00279 mol/l |
Class : | Soluble |
Log S (Ali) : | -1.91 |
Solubility : | 4.76 mg/ml ; 0.0122 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -4.03 |
Solubility : | 0.0366 mg/ml ; 0.000094 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.58 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.90 g (48.8%) | With sodium hydroxide; triethylamine; In acetonitrile; | Example 7 Synthesis of 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid using (PhO)3 B A mixture of 2.95 g of <strong>[112811-72-0]1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid</strong> (10 mmol), 3.75 g of 3-methylaminopiperidine 2HCl (20 mmol), 5.80 g of (PhO)3 B (20 mmol), 4.4 g of triethylamine (43 mmol) and 20 ml of acetonitrile was refluxed with heating for 6 hours. The reaction solution was cooled to room temperature, made acid with 6N--HCl and extracted with 10 ml of ethyl acetate twice. The pH of the water layer was adjusted to 8 to 9 with 25% NaOH, and separated crystals were filtered and dried to obtain 1.90 g (48.8%) of the objective compound. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | Example 3 1-Cyclopropyl-1,4-dihydro-6-fluoro-8-methoxy-7-(3-methylaminopiperidin-1-yl)-4-oxo-3-quinolinecarboxylic acid dihydrate An acetonitrile solution (30 mL) containing <strong>[112811-72-0]1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid</strong> (3 g), 3-methylaminopiperidine dihydrochloride (2.1 g), triethylamine (1.43 mL), and boron trifluoride-tetrahydrofuran complex (2.84 g) was stirred at room temperature for 2 hours. Triethylamine (5.71 mL) was further added to the reaction mixture, followed by stirring at room temperature for 24 hours. The solvent was evaporated under reduced pressure, and methanol (30 mL) was added to the residue. The mixture was refluxed for 6 hours, and the solvent was evaporated under reduced pressure. 80% Hydrated methanol (30 mL) was added to the residue, and the pH of the product was adjusted to 8 by use of 5N aqueous sodium hydroxide solution, followed by stirring at room temperature for 16 hours. The thus-produced crystals were recovered through filtration and dried, to thereby yield 3.98 g of the title compound (yield: 92%). 1H-NMR(400MHz,DMSO-d6) deltappm: 0.90-1.31(4H,m),1.31-2.12(4H,m),2.67-3.71(5H,m),3.77(3H,s),3.98-4.09(1H,m),7.85(1H,d,J=11.1Hz),8.78(1H,s) Elemental analysis: Calc. C;56.69%, H;6.62%, N;9.74% Obsd. C;56.48%, H;6.63%, N;9.86% | |
With triethylamine; In acetonitrile; | EXAMPLE 13 A mixture of <strong>[112811-72-0]1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid</strong> (2.95 g), 3-methylaminopiperidine dihydrochloride (6.69 g) and triethylamine (10 g) in acetonitrile (50 ml) was refluxed with stirring for 12 hours. The reaction mixture was concentrated in vacuum, and the residue was extracted with chloroform. The extract was washed with a saturated NaCl solution and concentrated in vacuo. The residue was purified by silica gel column chromatography (chloroform:methanol:ammoniumhydroxide=15:5:1) to give 1.28 g of 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-(3-methylaminopiperidin-1-yl)-4-oxoquinoline-3-carboxylic acid, which was recrystallized from acetonitrile-water, colorless needles. m.p. 134-135 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | With potassium carbonate In N,N-dimethyl-formamide at 40℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 27.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With potassium hydroxide In ethanol; water for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With potassium hydroxide In ethanol; water for 12h; Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium dodecyl-sulfate In aq. buffer at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium dodecyl-sulfate In aq. buffer at 20℃; for 0.25h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: sodium hydrogencarbonate / dichloromethane / 0.33 h / Cooling with ice 1.2: Cooling with ice 2.1: triethylamine / toluene 2.2: 110 - 120 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid With sodium hydrogencarbonate In dichloromethane for 0.333333h; Cooling with ice; Stage #2: 4-Chlorobutanoyl chloride In dichloromethane Cooling with ice; Stage #3: 2-pyrazylcarboxylic acid Further stages; | 21 Example 21 Add 1 mmol of banofloxacin and 2 mL of DCM to a 100 mL round bottom flask. Cooled in the ice bath, Magnetic stirring, Add 3mmol NaHCO3, After 20 minutes, A solution of 2.5 mmol of 4-chlorobutanoyl chloride in DCM (2 mL) was added dropwise with a constant pressure dropping funnel (drip acceleration of about 1d/2s). Continue to react under the ice bath. TLC was monitored until the end of the reaction. Stop stirring, Add 15 mL of H2O and 20 mL of DCM. Adjust pH=3-4 with 1N HCl solution with stirring. If there is a solid, it will stand still. Filtering, The filter cake was washed 3 times with DCM. The filter cake is left for further purification; The filtrate was transferred to a separatory funnel. Liquid separation, The aqueous phase was extracted with DCM (15 mL×1). Combine the organic phase, Wash with saturated NaCl solution (15 mL × 1), Collect organic phase, Dry with anhydrous Na2SO4. Rotary evaporator to spin dry to obtain a crude product. Column chromatography to obtain a pure product, Vacuum drying, An intermediate is obtained.1 mmol of the above intermediate was added to a 100 mL round bottom flask. 5mL toluene, 2mmol Et3N, Stir for 20-30min, Add 2mmol of pyrazinecarboxylic acid (POA), After 10 minutes, move to 110 ° C ~ 120 ° C oil bath to reflux reaction, TLC was monitored until the reaction was complete. The reaction solution was spun dry using a rotary evaporator rotary evaporator. Add 30mL DCM and stir to dissolve. Filtering, The filter cake was washed 3 times with DCM. The filtrate was washed with 10% citric acid solution (15 mL x 1). Collect organic phase, Dry with anhydrous Na2SO4. Rotary evaporator to spin dry to obtain a crude product. Column chromatography to obtain a pure product. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; | Synthesis of compound 2a-g General procedure: 0.32 g (1.0 eq, 1 mmol) 1a was dissolved in 10 mL waterfreeDMF, and 150 μL (1.5 eq, 1.5 mmol) TEA and 169 μL(2.2 eq, 2.2 mmol) chloroacetyl chloride were added insequence. The solution was stirred at room temperature for24 h, After the reaction completion detected by TLC, 30 mLof deionized water was added. After filtration, the filter cakewas washed with deionized water and dried overnight in thevacuum chamber, 0.27 g of the target compound 2a wasobtained in a yield of 73%.Compound 2b-g was synthesized in the same way ascompound 2a in yields of 70-88%. |
88% | With triethylamine In N,N-dimethyl-formamide at 20℃; for 24h; | Synthesis of compound 2a-g General procedure: 0.32 g (1.0 eq, 1 mmol) 1a was dissolved in 10 mL waterfreeDMF, and 150 μL (1.5 eq, 1.5 mmol) TEA and 169 μL(2.2 eq, 2.2 mmol) chloroacetyl chloride were added insequence. The solution was stirred at room temperature for24 h, After the reaction completion detected by TLC, 30 mLof deionized water was added. After filtration, the filter cakewas washed with deionized water and dried overnight in thevacuum chamber, 0.27 g of the target compound 2a wasobtained in a yield of 73%.Compound 2b-g was synthesized in the same way ascompound 2a in yields of 70-88%. |
73.12% | In N,N-dimethyl-formamide at 0 - 20℃; for 24.5h; | 14 Example 14 Synthesis of triazole Balofloxacin Take 0.389g of Balofloxacin, placed in a round bottom flask, add 10 mL DMF at 0 °C, stirring reaction at a constant rate for 10 min, slowly add chloroacetyl chloride 153µL, stir at 0 °C for 30 min, stir at room temperature for another 24 h, into the reaction solution add 3 times the volume of water, a large amount of insoluble matter was formed, stirred for another 1 hour, and filtered, the filter cake was dried to obtain an intermediate of 0.34 g, yield 73.12%. Weigh 0.1 g of intermediate, dissolved in 10mL acetonitrile, again added 22mg of sodium triazole, the reaction was carried out at 50 ° C for 48 h, and the reaction solution was concentrated, silica gel column chromatography and obtained new quinolone compound 0.078g, yield 58.33% (Synthetic route is shown in Figure 17) |
Stage #1: 1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-(3-methylaminopiperidin-1-yl)-3-quinolinecarboxylic acid With Sodium hydrogenocarbonate In dichloromethane for 0.333333h; Cooling with ice; Stage #2: chloroacetyl chloride In dichloromethane Cooling with ice; | 10 Example 10 Add 1 mmol of banofloxacin and 2 mL of DCM to a 100 mL round bottom flask. Cooled in the ice bath, Magnetic stirring, Add 3mmol NaHCO3, After 20 minutes, A 2.5 mmol solution of 2-chloroacetyl chloride in DCM (2 mL) was added dropwise with a constant pressure dropping funnel (drip acceleration was about 1 d / 2 s). Continue to react under the ice bath. TLC was monitored until the end of the reaction. Stop stirring, Add H2O15mL and DCM 20mL, Adjust pH=3-4 with 1N HCl solution with stirring. If there is a solid, it will stand still. Filtering, The filter cake was washed 3 times with DCM. The filter cake is left for further purification; The filtrate was transferred to a separatory funnel. Liquid separation, The aqueous phase was extracted with DCM (15 mL×1). Combine the organic phase, Wash with saturated NaCl solution (15 mL × 1), Collect organic phase, Dry with anhydrous Na2SO4. Rotary evaporator to spin dry to obtain a crude product. Column chromatography to obtain a pure product, Vacuum drying, Get the product. |