71083-06-2|Ethyl 8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate| Ambeed

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Quality Control of [ 71083-06-2 ] Purity: 95% SDS Specification

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Product Details of [ 71083-06-2 ]

CAS No. :	71083-06-2
Formula :	C₁₂H₁₀FNO₃
M.W :	235.21
SMILES Code :	O=C(C1=CNC2=C(C=CC=C2F)C1=O)OCC
MDL No. :	MFCD00052242
InChI Key :	MPUYCZQHTGRPNE-UHFFFAOYSA-N
Pubchem ID :	707160

Safety of [ 71083-06-2 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Computational Chemistry of [ 71083-06-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	10
Fraction Csp3	0.17
Num. rotatable bonds	3
Num. H-bond acceptors	4.0
Num. H-bond donors	1.0
Molar Refractivity	60.61
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	59.16 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.2
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.09
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.26
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.39
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.2
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.23

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.85
Solubility	0.33 mg/ml ; 0.00141 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.96
Solubility	0.257 mg/ml ; 0.00109 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-4.38
Solubility	0.00992 mg/ml ; 0.0000422 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.25 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.94

Application In Synthesis of [ 71083-06-2 ]

* 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.

Downstream synthetic route of [ 71083-06-2 ]

[ 71083-06-2 ] Synthesis Path-Downstream 1~35

1
[ 63010-68-4 ]
[ 71083-06-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 978 - 990.
[2]Magnetic Resonance in Chemistry,1996,vol. 34,p. 972 - 978.
[3]Journal of Medicinal Chemistry,2006,vol. 49,p. 6443 - 6450.
[4]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.
[5]RSC Advances,2014,vol. 4,p. 6254 - 6260.
[6]Journal of Medicinal Chemistry,2015,vol. 58,p. 560 - 576.
[7]Angewandte Chemie - International Edition,2017,vol. 56,p. 7282 - 7287.
Angew. Chem.,2017,vol. 129,p. 7388 - 7393,6.
[8]New Journal of Chemistry,2020,vol. 44,p. 11203 - 11214.

2
[ 78-40-0 ]
[ 71083-06-2 ]
1-Ethyl-8-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester [ No CAS ]

References: [1]Magnetic Resonance in Chemistry,1996,vol. 34,p. 972 - 978.

3
[ 111-86-4 ]
[ 71083-06-2 ]
8-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid octylamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2275 - 2279.

4
[ 71083-06-2 ]
[ 108-91-8 ]
N-cyclohexyl 8-fluoroquinol-4(1H)-one-3-carboxamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 2275 - 2279.

5
[ 71083-06-2 ]
[ 71082-99-0 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6443 - 6450.

6
[ 348-54-9 ]
[ 71083-06-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6443 - 6450.
[2]Magnetic Resonance in Chemistry,1996,vol. 34,p. 972 - 978.
[3]RSC Advances,2014,vol. 4,p. 6254 - 6260.
[4]European Journal of Medicinal Chemistry,2014,vol. 86,p. 318 - 334.
[5]Journal of Medicinal Chemistry,2015,vol. 58,p. 560 - 576.
[6]Angewandte Chemie - International Edition,2017,vol. 56,p. 7282 - 7287.
Angew. Chem.,2017,vol. 129,p. 7388 - 7393,6.
[7]New Journal of Chemistry,2020,vol. 44,p. 11203 - 11214.

7
[ 87-13-8 ]
p-NH₂-C₆H₄-COOR [ No CAS ]
[ 71083-06-2 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6443 - 6450.

8
[ 87-13-8 ]
sodium compound of acetonedicarboxylic acid diethyl ester [ No CAS ]
[ 71083-06-2 ]

References: [1]Magnetic Resonance in Chemistry,1996,vol. 34,p. 972 - 978.

9
[ 71083-06-2 ]
[ 824-94-2 ]
ethyl 8-fluoro-1-(4-methoxybenzyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃; for 18h;	8-fluoro- 1 -(4-methoxybenzyl)-4-oxo~ 1 ,4-dihydroquinoline-3 -carboxylic acid; 5-2: ethyl 8-fluoro-l-(4-methoxybenzyl)-4-oxo-l,4-dihydroquinoline-3-carboxylate; Commercially available quinolcme 5-1 (200 mg, 0.85 mmol) (Acros Organics) was dissolved in 2 mL anhydrous DMF and treated with potassium carbonate (353 mg, 2.55 mmol), potassium iodide (~10 mg), and 4-methoxybenzyl chloride (136 mg, 0.867 mmol). After 18 h at ambient temperature, sat. aq. ammonium chloride was added (~5 mL), followed by excess water. The precipitate was filtered and washed with water. The solid 5-2 was used in the next step without purification. 1H NMR (CDCl3, 300 MHz): 8.52 (s, IH), 8.35 (m, IH), 7.32 (m, 2H), 7.10 (d, J= 8.4 Hz, 2H), 6.88 (d, J= 8.4 Hz, 2H), 5.48 (s, 2H), 4.40 (q, 2H), 3.75 (s, 3H), 1.41 (t, 3H); MS (Electrospray): m/z 356.0 (MH+).

References: [1]Patent: WO2007/67489,2007,A1 .Location in patent: Page/Page column 37-38.

10
[ 452-07-3 ]
[ 71083-06-2 ]
ethyl 1-(2,4-difluorobenzyl)-8-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 20℃; for 18h;	EXAMPLE 6; 1 -(2,4-difluorobenzyl)-8-fluoro-4-oxo-l ,4-dihydroquinoline-3-carboxylic acid; 6-2: ethyl l-(2,4-difluorobenzyl)-8-fluoro-4-oxo-l,4-dihydroquinoline-3-carboxylate; Commercially available quinolone 5-1 (200 mg, 0.85 mmol) (Acros Organics) was dissolved in 2 mL anhydrous DMF and treated with potassium carbonate (353 mg, 2.55 mmol), potassium iodide (-10 mg), and 2,4-difluoroben2yl chloride (141 mg, mL, 0.87 mmol). After 18 h at ambient temperature, sat. aq. ammonium chloride was added (~5 mL), followed by excess water. The precipitate was filtered and washed with water. The solid 6-2 was used in the next step without purification. 1H NMR (CD3OD, 300 MHz): 8.71 (s, IH), 8.13 (d, J= 8.1 Hz, IH), 7.60-7.40 (m, 2H), 7.07-6.90 (m, 3H), 5.77 (s, 2H), 4.30 (q, 2H), 1.39 (t, 3H); MS (Electrospray): m/z 362.0 (MH+).

References: [1]Patent: WO2007/67489,2007,A1 .Location in patent: Page/Page column 38-39.

11
[ 71083-06-2 ]
[ 63010-71-9 ]

References: [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 978 - 990.

12
[ 71083-06-2 ]
[ 13035-61-5 ]
[ 934000-17-6 ]

References: [1]Collection of Czechoslovak Chemical Communications,2006,vol. 71,p. 978 - 990.

14
[ 380893-61-8 ]
[ 71083-06-2 ]
[ 1193116-77-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 60℃; for 15h;Inert atmosphere;	To a solution of ethyl-8-fluoro-4-oxo-l,4-dihydroquinoline-3-carboxylate (5.00 g,21.3 mmol) in 50 mL of DMF under nitrogen was added the above compound (8.48 g, 31.9 mmol), potassium iodide (0.176 g, 1.06 mmol), and potassium carbonate (3.53 g, 25.5 mmol). The reaction mixture was stirred at 6O0C for 15 hours, cooled to room temperature, and diluted with 200 mL of water. The resulting solid was washed with water (2 x 100 mLl) and diethyl0 ether (2 x 75 mL) and dried in vacuo to provide ethyl l-[(5-bromopyridin-2-yl)methyl]-8-fluoro- 4-oxo- l,4-dihydroquinoline-3-carboxylate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 407.0 for M+H+(81Br).

References: [1]Patent: WO2009/134668,2009,A2 .Location in patent: Page/Page column 14; 31.

15
[ 71083-06-2 ]
2-bromo-5-halomethylpyridine [ No CAS ]
[ 1216947-20-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1334 - 1337.

16
[ 71083-06-2 ]
3-bromo-6-halomethylpyridazine [ No CAS ]
[ 1216947-23-7 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1334 - 1337.

17
[ 71083-06-2 ]
4-bromobenzyl halide [ No CAS ]
[ 1207749-45-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1334 - 1337.

18
[ 71083-06-2 ]
5-bromo-2-halomethylpyridine [ No CAS ]
[ 1193116-77-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1334 - 1337.

19
[ 71083-06-2 ]
2-halomethylnaphthalene [ No CAS ]
C₂₃H₁₈FNO₃ [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 2769 - 2772.

20
[ 71083-06-2 ]
[ 1435910-97-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.

21
[ 71083-06-2 ]
[ 1435911-04-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.

22
[ 71083-06-2 ]
[ 106-89-8 ]
[ 1435910-89-6 ]

Yield	Reaction Conditions	Operation in experiment
88.3%	With potassium carbonate; at 120℃; for 3h;	General procedure: A mixture of compound 2a (0.253 g, 1.0 mmol) and potassium carbonate (0.151 g, 1.2 mmol) was stirred under reflux in 2-(chloromethyl)oxirane (15 mL) for 3 h. When the reaction was completed (monitored by TLC, eluent, chloroform/methanol 70/1,V/V), the mixture was cooled to room temperature, and then the excess 2-(chloromethyl)oxirane was evaporated under reduced pressure. After water was added, the resulting mixture was extracted with chloroform (3 x 20 mL). The combined organic phase was dried over anhydrous Na2SO4, and then the solvent was evaporated. The residue was purified via silica gel column chromatography (eluent, chloroform/methanol = 70/1, V/V) to give compound 3a (0.294 g) as light yellow solid.
	With potassium carbonate; at 120℃; for 3h;	General procedure: A mixture of compound 3 (0.253 g, 1.0 mmol) and potassium carbonate (0.151 g, 1.2 mmol) was stirred in 2-(chloromethyl)oxirane (15 mL) under reflux for 3 h. After the reaction was completed, the mixture was cooled to room temperature, the excess 2-(chloromethyl) oxirane was evaporated under reduced pressure, and water was added. The residue was extracted with chloroform (3 20 mL), the combined organic phase was dried over anhydrous sodium sulfate, and then the residue was purified by column chromatography (eluent, chloroform/methanol 70:1, V/V) to give the desired compound 4a (0.294 g) as light yellow solid.

References: [1]European Journal of Medicinal Chemistry,2014,vol. 86,p. 318 - 334.
[2]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.

23
[ 105-53-3 ]
[ 71083-06-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.

24
[ 87-13-8 ]
[ 71083-06-2 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 3267 - 3272.
[2]RSC Advances,2014,vol. 4,p. 6254 - 6260.
[3]Journal of Medicinal Chemistry,2015,vol. 58,p. 560 - 576.
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 7282 - 7287.
Angew. Chem.,2017,vol. 129,p. 7388 - 7393,6.
[5]New Journal of Chemistry,2020,vol. 44,p. 11203 - 11214.

25
[ 71083-06-2 ]
ethyl 8-fluoro-1,4-dihydro-1-methyl-4-oxo-6-phenylquinoline-3-carboxylate [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 6254 - 6260.

26
[ 71083-06-2 ]
ethyl 8-fluoro-6-(4-fluorophenyl)-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylate [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 6254 - 6260.

27
[ 71083-06-2 ]
ethyl 8-fluoro-1,4-dihydro-1-methyl-6-(5-methylthiophen-2-yl)-4-oxoquinoline-3-carboxylate [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 6254 - 6260.

28
[ 71083-06-2 ]
ethyl 8-fluoro-1,4-dihydro-1-methyl-4-oxo-6-(thiophen-2-yl)quinoline-3-carboxylate [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 6254 - 6260.

29
[ 71083-06-2 ]
[ 74-88-4 ]
ethyl 8-fluoro-1,4-dihydro-1-methyl-4-oxoquinoline-3-carboxylate [ No CAS ]

References: [1]RSC Advances,2014,vol. 4,p. 6254 - 6260.

30
C₁₅H₁₈FNO₄ [ No CAS ]
[ 71083-06-2 ]