1394820-98-4|4-(2-Fluoro-4-nitrophenoxy)quinolin-7-ol| Ambeed

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Quality Control of [ 1394820-98-4 ] Purity: 95% SDS Specification

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Product Details of [ 1394820-98-4 ]

CAS No. :	1394820-98-4
Formula :	C₁₅H₉FN₂O₄
M.W :	300.24
SMILES Code :	OC1=CC=C2C(OC3=CC=C([N+]([O-])=O)C=C3F)=CC=NC2=C1
MDL No. :	MFCD28142879
InChI Key :	ORSCRIJOVRKFEO-UHFFFAOYSA-N
Pubchem ID :	135742175

Safety of [ 1394820-98-4 ]

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

Computational Chemistry of [ 1394820-98-4 ] Show Less

Physicochemical Properties

Num. heavy atoms	22
Num. arom. heavy atoms	16
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	6.0
Num. H-bond donors	1.0
Molar Refractivity	79.06
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	88.17 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.93
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	3.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.2
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.	1.65
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	1.24
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.46

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.11
Solubility	0.0231 mg/ml ; 0.0000768 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-4.82
Solubility	0.00458 mg/ml ; 0.0000152 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-5.03
Solubility	0.00279 mg/ml ; 0.00000929 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	No
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	Yes
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	Yes
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	Yes
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	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.8 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	2.0 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<0.0
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)	2.33

Application In Synthesis of [ 1394820-98-4 ]

* 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 [ 1394820-98-4 ]

[ 1394820-98-4 ] Synthesis Path-Downstream 1~35

1
[ 1484-26-0 ]
[ 1394820-98-4 ]

References: [1]Patent: US2012/219522,2012,A1 .

2
[ 749922-34-7 ]
[ 1394820-98-4 ]

References: [1]Patent: US2012/219522,2012,A1 .

3
[ 178984-56-0 ]
[ 1394820-98-4 ]

References: [1]Patent: US2012/219522,2012,A1 .
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.

4
[ 909345-85-3 ]
[ 1394820-98-4 ]

References: [1]Patent: US2012/219522,2012,A1 .

5
[ 558-30-5 ]
[ 1394820-98-4 ]
[ 1394820-99-5 ]

Yield	Reaction Conditions	Operation in experiment
42.5%	With sodium hydroxide; In tetrahydrofuran; water; at 20 - 45℃; for 10h;	Step 6) 1-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropan-2-ol To a solution of <strong>[1394820-98-4]4-(2-fluoro-4-nitrophenoxy)quinolin-7-ol</strong> (60 g, 0.2 mol) in THF/H2O (1 L, THF/H2O=1:1, v/v) was added NaOH (24 g, 0.6 mol) at room temperature, followed by isobutylene oxide (144 g, 2 mol). The reaction was stirred at 45 C. for 10 hours, and then diluted with EtOAc (1 L). The resulted solution was washed with 1 M NaOH aqueous solution (500 mL*4). The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The residue was washed with 500 mL of petroleum ether, and collected through filtration to give the title compound as a light yellow solid (31.6 g, 42.5%). MS (ESI, pos. ion) m/z: 373.1 [M+1]; 1H NMR (400 MHz, CDCl3): delta 1.41 (s, 6H), 2.28 (s, 1H), 3.98 (s, 2H), 6.53-6.54 (d, J=5.2 Hz, 1H), 7.26-7.36 (m, 2H), 7.45-7.46 (d, J=2.4 Hz, 1H), 8.12-8.20 (m, 3H), 8.69-8.70 (d, J=4.8 Hz, 1H).

References: [1]Patent: US2012/219522,2012,A1 .Location in patent: Page/Page column 21.

6
[ 1394820-97-3 ]
[ 1394820-98-4 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydrogenchloride; water; In 1,4-dioxane; at 100℃; for 24h;	Step 5) 4-(2-fluoro-4-nitrophenoxy)quinolin-7-ol A suspension of 7-(benzyloxy)-4-(2-fluoro-4-nitrophenoxy)quinoline (100 g, 256.4 mmol) in dioxane (425 mL) and conc. HCl (425 mL, 5.1 mol) was stirred at 100 C. for 24 hours. The reaction mixture was then cooled to room temperature and solid was collected through filtration. The solid was then suspended in anhydrous EtOH (100 mL) and stirred for 2 hours. The solid was collected and dried in vacuo at 60 C. for 12 hours to give the title compound as a pale solid (73.3 g, 85%). MS (ESI, pos. ion) m/z: 301 [M+1]; 1H NMR (400 MHz, DMSO-d6): delta 7.06-7.07 (d, J=6.8 Hz, 1H), 7.51-7.54 (m, 1H), 7.71 (s, 1H), 7.89-7.94 (m, 1H), 8.28-8.30 (d, J=8.8 Hz, 1H), 8.41-8.43 (d, J=9.6 Hz, 1H), 8.51-8.54 (d, J=10 Hz, 1H), 8.94-8.96 (d, J=6.4 Hz, 1H), 12.00 (s, 1H).

References: [1]Patent: US2012/219522,2012,A1 .Location in patent: Page/Page column 20.
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.

7
[ 1394820-98-4 ]
[ 1394820-91-7 ]

References: [1]Patent: US2012/219522,2012,A1 .

8
[ 1394820-98-4 ]
[ 1394821-11-4 ]

References: [1]Patent: US2012/219522,2012,A1 .

9
[ 1394820-98-4 ]
[ 1394821-12-5 ]

References: [1]Patent: US2012/219522,2012,A1 .

10
[ 1394820-98-4 ]
[ 1394821-13-6 ]

References: [1]Patent: US2012/219522,2012,A1 .

11
[ 67-66-3 ]
[ 1394820-98-4 ]
[ 67-64-1 ]
[ 1394821-10-3 ]

Yield	Reaction Conditions	Operation in experiment
36.4%	With sodium hydroxide; at 20℃; for 1h;	Step 1) 2-((4-(2-fluoro-4-nitrophenoxy)quinolin-7-yl)oxy)-2-methylpropanoic acid To a mixture of <strong>[1394820-98-4]4-(2-fluoro-4-nitrophenoxy)quinolin-7-ol</strong> (5 g, 16.7 mmol) and NaOH (6.7 g, 166.7 mmol) in acetone (67 mL) was added chloroform (21.9 g, 183.3 mmol) dropwise at room temperature. After the mixture turned brown color, the reaction was heated to reflux for 1 hour. Water (10 mL) was then added to the reaction mixture, and the resulted solution was adjusted to pH 3~4 with 1 N HCl solution. The resulted mixture was concentrated in vacuo, and then extracted with EtOAc (30 mL). The organic phase was separated, concentrated in vacuo, and treated with 95% EtOH (10 mL). The resulted solid was collected by filtration, dried in vacuo overnight to afford the title compound as a brown solid (2.34 g, 36.4%). LC-MS (ESI, pos, ion) m/z: 387 [M+1]; 1H NMR (400 MHz, CDCl3): delta 1.92 (s, 6H), 6.48-6.49 (m, 1H), 7.27-7.40 (m, 2H), 7.82 (d, 1H, J=2.44 Hz), 8.13-8.19 (m, 3H), 8.54 (d, J=5.6 Hz, 1H).

References: [1]Patent: US2012/219522,2012,A1 .Location in patent: Page/Page column 27.

12
[ 1394820-98-4 ]
[ 1394820-69-9 ]

References: [1]Patent: US2012/219522,2012,A1 .

13
[ 1394820-98-4 ]
[ 1394821-00-1 ]

References: [1]Patent: US2012/219522,2012,A1 .
[2]European Journal of Medicinal Chemistry,2020,vol. 192.

14
[ 403-19-0 ]
[ 1394820-98-4 ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.
[2]European Journal of Medicinal Chemistry,2020,vol. 192.

15
[ 1394820-98-4 ]
[ 2031-23-4 ]
4-(2-fluoro-4-nitrophenoxy)-7-[3-(4-methylpiperazin-1-yl)propoxy]quinoline [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.

16
[ 1394820-98-4 ]
3-fluoro-4-{7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yloxy}phenylamine [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.

17
[ 1394820-98-4 ]
N-(3-fluoro-4-{7-[3-(4-methylpiperazin-1-yl)propoxy]quinolin-4-yloxy}phenyl)-2-trifluoromethylbenzenesulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 6277 - 6292.

18
[ 1039046-51-9 ]
[ 1394820-98-4 ]

Yield	Reaction Conditions	Operation in experiment
60%	With boron tribromide; In dichloromethane; at -50 - 20℃;	To a solution of 4-(2-fluoro-4-nitrophenoxy)-7-methoxyquinoline 12 (8g, 25.4mmol) in DCM (80mL) was added drop-wise a solution of boron tribromide (76.4mmol) in DCM (30mL) at-50C and subsequently stirred for 1h. And then the mixture was warmed to room temperature and stirred overnight. The reaction mixture was poured into ice-water slowly and alkalized to pH 12 with saturated sodium hydroxide solution cautiously. After the organic layer was separated, the aqueous phase was acidated to pH 6 with 1N HCl with solid precipitated. The resulting suspension was filtered the solid dried to afford the title compound 13 as a yellow solid (4.6g, 60%); m.p. 248-250C (250-252C, ref 24); 1H NMR (400MHz, DMSO-d6) delta 11.68 (s, 1H, -OH), 9.00 (d, J=6.4Hz, 1H, Ar-H), 8.56 (dd, J=10.0, 1.6Hz, 1H, Ar-H), 8.43 (d, J=9.6Hz, 1H, Ar-H), 8.31 (d, J=8.8Hz, 1H, Ar-H), 7.91 (t, J=8.4Hz, 1H, Ar-H), 7.61-7.38 (m, 2H, Ar-H), 7.10 (d, J=6.4Hz, 1H, Ar-H); MS (ESI) m/z: 301.3 [M+H]+.