25199-84-2|2-Hydroxy-4-(trifluoromethyl)quinoline| Ambeed

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Quality Control of [ 25199-84-2 ] Purity: 95% SDS Specification

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Product Details of [ 25199-84-2 ]

CAS No. :	25199-84-2
Formula :	C₁₀H₆F₃NO
M.W :	213.16
SMILES Code :	OC2=NC1=CC=CC=C1C(=C2)C(F)(F)F
MDL No. :	MFCD03407380
InChI Key :	UUROBWTVZZNDFD-UHFFFAOYSA-N
Pubchem ID :	2759347

Safety of [ 25199-84-2 ]

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

Computational Chemistry of [ 25199-84-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	10
Fraction Csp3	0.1
Num. rotatable bonds	1
Num. H-bond acceptors	5.0
Num. H-bond donors	1.0
Molar Refractivity	48.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	33.12 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.95
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	3.05
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	4.11
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.	2.6
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	2.92
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.93

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.51
Solubility	0.0658 mg/ml ; 0.000309 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.	-3.41
Solubility	0.0826 mg/ml ; 0.000388 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	-4.02
Solubility	0.0204 mg/ml ; 0.0000957 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.	-5.43 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)	1.58

Application In Synthesis of [ 25199-84-2 ]

* 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 [ 25199-84-2 ]

[ 25199-84-2 ] Synthesis Path-Downstream 1~35

1
1-Isocyanato-2-(1-trifluoromethyl-vinyl)-benzene [ No CAS ]
[ 25199-84-2 ]

References: [1]Journal of the American Chemical Society,1997,vol. 119,p. 12366 - 12367.

2
[ 62-53-3 ]
[ 372-31-6 ]
[ 25199-84-2 ]

Yield	Reaction Conditions	Operation in experiment
46.5%		A mixture of aniline (9.30 g, 100 mmol) and ethyl 4,4,4-trifluoro-3-oxobutanoate (36.8 g, 200 mmol) was stirred at 110 C for 1 hour. The reaction mixture was concentrated under reduced pressure, and then diluted with water (20 mL). Conc. H2S04 (110 g, 1.13 mol) was added carefully and the mixture stirred at 90C forhour, then cooled to room temperature and poured into ice water (500 mL). The precipitate was collected by filtration, and then recrystallised from ethanol (50 mL) to give the title compound (9.90 g, 46.5% yield) as a white solid. ?H NMR (400 MHz, DMSO-d6): 12.34 (bs, 1H), 7.75 (m, 2H), 7.45 (d, 1H), 7.32 (m, 1H), 6.99 (s, 1H). MS mlz 214.20 [M+Hjt
		General Procedure 98: 4-Trifluoromethyl-1H-quinolin-2-one (Intermediate 465)Aniline (7.0 g, 75.3 mmol) and trifluoro ethylacetoacetate (15.4 ml, 105 mmol) were heated at 110 C. for 45 min. The excess ester was removed in vacuo. 75% H2SO4 was added and the mixture was heated at 90 C. for 45 min. After cooling, the mixture was poured onto ice and the resulting precipitate was collected by filtration to give title compound (7.0 g, 44%) which was used in the next step without further purification.MW: 212.15HPLCMS (Method C): [m/z]: 214
	With triethylamine; In toluene;Heating / reflux;	To a solution of the ester (5.46 mmol) and triethylamine (101 g, 10.86 mmol) in toluene (5 mL) was added a solution of aniline (6.52 mmol) in toluene (2 mL) at room temperature. The reaction mixture was refluxed until the reaction was complete. After workup, compound 56 was obtained, which was pure enough to be used in the next step.

References: [1]Synthesis,2003,p. 2005 - 2010.
[2]Patent: WO2018/165385,2018,A1 .Location in patent: Paragraph 00362.
[3]European Journal of Organic Chemistry,2003,p. 2115 - 2121.
[4]Patent: US2012/214803,2012,A1 .Location in patent: Page/Page column 172.
[5]Patent: US2008/275057,2008,A1 .Location in patent: Page/Page column 86.

3
[ 25199-84-2 ]
[ 590372-17-1 ]

References: [1]European Journal of Organic Chemistry,2003,p. 2115 - 2121.
[2]Journal of the American Chemical Society,2011,vol. 133,p. 8317 - 8325.

4
[ 836-31-7 ]
[ 25199-84-2 ]

References: [1]European Journal of Organic Chemistry,2004,p. 54 - 63.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6143 - 6146.

5
ethyl 3-{2-[(tert-butoxycarbonyl)amino]phenyl}-4,4,4-trifluorobut-2-enoate [ No CAS ]
[ 25199-84-2 ]

References: [1]European Journal of Organic Chemistry,2006,p. 3147 - 3151.

6
[ 25199-84-2 ]
[ 328956-38-3 ]

References: [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 6143 - 6146.
[2]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.

7
[ 25199-84-2 ]
[ 328955-57-3 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6143 - 6146.

8
[ 25199-84-2 ]
6-bis(ethylamino)-4-trifluoromethylquinolin-2(1H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6143 - 6146.

9
[ 25199-84-2 ]
6-(dipropylamino)-4-(trifluoromethyl)quinolin-2(1H)-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.
[2]Journal of Medicinal Chemistry,2006,vol. 49,p. 6143 - 6146.

10
[ 25199-84-2 ]
6-[bis-(2,2-difluoro-ethyl)-amino]-4-trifluoromethyl-1H-quinolin-2-one [ No CAS ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 1527 - 1531.

11
[ 62-53-3 ]
α-chloro-propionic acid amide [ No CAS ]
[ 25199-84-2 ]