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Chemical Structure| 139-59-3 Chemical Structure| 139-59-3
Chemical Structure| 139-59-3

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CAS No.: 139-59-3

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Product Citations

Product Citations

Beteck, Richard M ; Legoabe, Lesetja J ; Dube, Phelelisiwe S , et al.

Abstract: Diphenyl ether and quinoline based compounds have been reported to show antibacterial activity. Against Mycobacterium tuberculosis, drug targets inhibited by diphenyl ether compounds are reportedly different from those perturbed by quinoline based antitubercular hits/drugs. Herein, we conceptualized and synthesized novel molecules incorporating quinoline and diphenyl ether moieties. The antitubercular property of the synthesized compounds were measured in vitro using Tween 80 and Tyloxapol supplemented growth media. Compounds in this study generally showed sub micromolar antitubercular activity in tween 80/ albumin supplemented growth medium, and moderate to poor activity in tyloxapol/casitone supplemented growth medium. Compound 4e, havin a trimethylenediamine moiety and low melting point of 68°C, emerged as the hit compound, possessing MIC90 value of 0.2 μM. 4e is non-cytotoxic when tested against normal human cell line, exhibiting CC50 value > 20 μM.

Keywords: Quinoline ; Diphenyl ether ; Tuberculosis ; Cytotoxicity ; Antitubercular

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Product Details of [ 139-59-3 ]

CAS No. :139-59-3
Formula : C12H11NO
M.W : 185.22
SMILES Code : NC1=CC=C(OC2=CC=CC=C2)C=C1
MDL No. :MFCD00007862
InChI Key :WOYZXEVUWXQVNV-UHFFFAOYSA-N
Pubchem ID :8764

Safety of [ 139-59-3 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H317-H319-H335
Precautionary Statements:P261-P280-P305+P351+P338

Calculated chemistry of [ 139-59-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 14
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 1.0
Num. H-bond donors 1.0
Molar Refractivity 57.36
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

35.25 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

2.15
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

2.93
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

3.07
Log Po/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.

2.68
Log Po/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

2.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.63

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-3.34
Solubility 0.0853 mg/ml ; 0.000461 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.

-3.33
Solubility 0.0863 mg/ml ; 0.000466 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

-4.3
Solubility 0.00937 mg/ml ; 0.0000506 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

 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

 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.

-5.35 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

 1.0
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.

1.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 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)

 1.42

Application In Synthesis [ 139-59-3 ]

* 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 [ 139-59-3 ]

[ 139-59-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 39213-20-2 ]
  • [ 139-59-3 ]
  • 3,5-dibromo-benzenesulfonic acid-(4-phenoxy-anilide) [ No CAS ]
  • 2
  • [ 5319-77-7 ]
  • [ 594-42-3 ]
  • [ 139-59-3 ]
  • [ 69949-88-8 ]
  • 3
  • [ 28785-06-0 ]
  • [ 139-59-3 ]
  • [ 54758-81-5 ]
  • 4
  • [ 139-59-3 ]
  • [ 214476-78-5 ]
  • 8-methoxy-4-(4-phenoxy-phenylamino)-quinoline-3-carbonitrile [ No CAS ]
  • 5
  • [ 62124-43-0 ]
  • [ 139-59-3 ]
  • (4-phenoxy-phenyl)-(5-phenyl-oxazol-2-yl)-amine [ No CAS ]
  • 6
  • [ 139-59-3 ]
  • [ 364793-57-7 ]
  • 7-bromo-4-(4-phenoxyanilino)-3-quinolinecarbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With pyridine hydrochloride; In 1-ethoxyethanol; REFERENCE EXAMPLE 10 7-Bromo-4-(4-phenoxyanilino)-3-quinolinecarbonitrile A mixture of 4-phenoxyaniline (204 mg, 1.1 mmol), <strong>[364793-57-7]7-bromo-4-chloro-3-quinolinecarbonitrile</strong> (267 mg, 1.0 mmol) and pyridine hydrochloride (20 mg) in 10 mL of ethoxyethanol was heated at reflux for 1 hour. The mixture was cooled, poured into 5% sodium carbonate solution, and stirred. The product was filtered, washed with water, and dried to provide 396 mg (95% yield) of 7-bromo-4-(4-phenoxyanilino)-3-quinolinecarbonitrile as a tan solid, mp 205-207 C; 1H NMR (DMSO-d6) delta 7.05 (m, 4H), 7.10 (t, J=7 Hz, 1H), 7.27 (dd, J=7, 2 Hz, 2H), 7.37 (in, 2H), 7.72 (dd, J=9, 2 Hz, 1H), 8.01 (d, J=2 Hz, 1H), 8.41 (t, J=4 Hz, 2H), 10.02 (s, 1H); MS (ES) mlz 416.1 (M+1). Analysis for C22Hl4 BrN3O: Calcd: C, 63.48;H, 3.39; N, 10.09. Found: C, 63.12;H, 3.29; N, 10.00.
  • 7
  • [ 53911-68-5 ]
  • [ 139-59-3 ]
  • [ 1221962-01-1 ]
YieldReaction ConditionsOperation in experiment
A solution of triethyl amine (1.5 ml) in 1,4-dioxane (5 ml) was added to a mixture of commercial 4- phenoxyaniline (1.85 g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong>. The resulting solution was stirred at rt for 0.5 h and at 400C for 2 h. Under cooling with ice cone. HCI (2 ml) and water (10 ml) was added. A gummy precipitate is formed from which the aqueous layer is removed by decantation. Crystallisation was induced by heating with methanol (5 ml). After cooling in the refrigerator the precipitate was isolated by filtration, washed with methanol and diethyl ether, and dried in vacuo to give colourless, powdery crystals (3 g) of /V-(4-phenoxyphenyl)-3-(4-chlorophenyl)- glutaramic acid.
A solution of triethyl amine (1.5 ml) in 1,4-dioxane (5 ml) was added to a mixture of commercial 4-phenoxyaniline (1.85 g) and <strong>[53911-68-5]3-(4-chlorophenyl)glutaric anhydride</strong>. The resulting solution was stirred at rt for 0.5 h and at 40 C. for 2 h. Under cooling with ice conc. HCl (2 ml) and water (10 ml) was added. A gummy precipitate is formed from which the aqueous layer is removed by decantation. Crystallisation was induced by heating with methanol (5 ml). After cooling in the refrigerator the precipitate was isolated by filtration, washed with methanol and diethyl ether, and dried in vacuo to give colourless, powdery crystals (3 g) of N-(4-phenoxyphenyl)-3-(4-chlorophenyl)-glutaramic acid
  • 8
  • [ 33332-28-4 ]
  • [ 139-59-3 ]
  • [ 1366234-44-7 ]
  • 9
  • [ 82413-63-6 ]
  • [ 27318-90-7 ]
  • [ 139-59-3 ]
  • 4-(4-(1-(4-phenoxyphenyl)-1H-imidazo[4,5-f ][1,10]phenanthrolin-2-yl)benzyl)morpholine [ No CAS ]
  • 10
  • [ 22200-50-6 ]
  • [ 139-59-3 ]
  • (4-phenoxyphenyl)-(7-iodoquinolin-4-yl)amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% In butan-1-ol; at 120℃; (4-Phenoxyphenyl)-(7-iodoquinolin-4-yl)amine (0635) 4-Chloro-7-iodoquinoline (10 g, 34 mmol) [Semenov, V. P.; Studenikov, A. N. Synthesis of 7-iodo-4-aminoquinoline derivatives. Khim. Geterotsikl. Soedin. (1980), Issue 7, 972-5] and 4-phenoxyaniline (6.38 g, 34 mmol) in butanol (75 ml) were heated at gentle reflux (120° C.) overnight (18 hrs). On cooling the resultant precipitate was collected by filtration and washed with acetonitrile (2×50 ml). The resultant solid was suspended in chloroform (500 ml) and 2N sodium carbonate solution (300 ml) and heated at 75° C. for 45 mins. On cooling the resultant precipitate was collected by filtration, washed with water (2×50 ml) and dried to yield the product as a pale brown solid. (9.95 g, 66percent) deltaH [2H6] DMSO 8.35 (3H, m), 8.20 (1H, s), 8.10 (1H, d), 7.85 (1H, s), 7.35 (4H, m), 7.15 (4H, d), 6.75 (1H, d).
  • 11
  • [ 55496-69-0 ]
  • [ 139-59-3 ]
  • 7-methoxy-6-nitro-N-(4-phenoxyphenyl)quinazolin-4-amine [ No CAS ]
  • 12
  • [ 160893-07-2 ]
  • [ 139-59-3 ]
  • 5-methoxy-N-(4-phenoxyphenyl)quinolin-2-amine [ No CAS ]
  • 13
  • [ 117997-81-6 ]
  • [ 139-59-3 ]
  • benzyl N4-[(1,1-dimethylethoxy)carbonyl]-N5-[4-(phenoxy)phenyl]-1-glutamic acid ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of Boc-Glu(OBn)-OH (3.5 g, 10 mmol) and N-methylmorpholine (2.2 mL, 2 eq) in THF (20 mL) at -20 C. was added isobutyl chloroformate (1.2 mL, 1 eq). After stirring at this temperature for 30 min, 4-benzyloxyaniline (2 g, 1 eq) was added and the turbid reaction was allowed to warm to room temperature over 16 h. The reaction was filtered and concentrated. The residue was dissolved in EtOAc, washed with NaHSO4 (sat. aq.), NaHCO3 (sat. aq.) and brine, dried and concentrated.
  • 14
  • [ 32703-79-0 ]
  • [ 139-59-3 ]
  • 5-(tert-butyl)-2-(4-phenoxyphenyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% In acetic acid;Reflux; General procedure: A 10 mL round bottomed flask was charged with 1 (1.00 mmol), 2 (1.00 mmol), acetic acid (5 mL) and provided with a reflux condenser. The reaction mixture was heated to reflux and stirred for an appropriate period. TLC was used to monitor the progress of the reaction. After completion of the reaction, the mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with water (2 x 20 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated in a rotary evaporator under reduced pressure. The crude mixture was purified by column chromatography to afford the pure products (3a-3g?).
  • 15
  • [ 117-21-5 ]
  • [ 139-59-3 ]
  • 4-chloro-2-(4-phenoxyphenyl)isoindoline-1,3-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With acetic acid; at 110℃; for 4h; General procedure: The starting materials 1 and 2 were commercially available (Energy Chemical, Shanghai, China).Compound 2 (3.72 mmol) was added to a stirred solution of compound 1 (3.38 mmol) in glacial aceticacid (10 mL). The reaction mixture was then stirred at 110 C for 4 h. After completion of the reaction,the solvent was evaporated, and the residue was purified on a silica gel column chromatography andeluted with ethyl acetate/petroleum ether (bp 60-90 C) (1:3, v/v) to give compounds 3.
75% In acetic acid;Reflux; General procedure: A 10 mL round bottomed flask was charged with 1 (1.00 mmol), 2 (1.00 mmol), acetic acid (5 mL) and provided with a reflux condenser. The reaction mixture was heated to reflux and stirred for an appropriate period. TLC was used to monitor the progress of the reaction. After completion of the reaction, the mixture was diluted with water (20 mL) and extracted with ethyl acetate (3 x 20 mL). The combined organic layers were washed with water (2 x 20 mL), brine (20 mL), dried over anhydrous Na2SO4, filtered and evaporated in a rotary evaporator under reduced pressure. The crude mixture was purified by column chromatography to afford the pure products (3a-3g’).
  • 16
  • [ 4481-28-1 ]
  • [ 139-59-3 ]
  • C20H16N2O3 [ No CAS ]
  • 17
  • [ 70395-35-6 ]
  • [ 139-59-3 ]
  • 2-chloro-2-fluoro-N-(4-phenoxyphenyl)acetamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 0 - 20℃; for 1.3h; General procedure: To a stirred solution of 5-amino-1-naphthol (126 mg, 0.792 mmol) and <strong>[70395-35-6]sodium chlorofluoroacetate</strong> (159 mg,1.18 mmol) in dichloromethane (8 mL) was added T3P (50 wt%solution in AcOEt, 701 μL, 1.18 mmol) and N,N-diisopropylethylamine(DIPEA) (273 μL, 1.57 mmol) at 0C. Afterstirred at ambient temperature for 1 h, the reaction mixturewas diluted with water and extracted thrice with CHCl3. Thecombined organic layers were washed with brine, dried overNa2SO4, filtered and concentrated in vacuo. The residue waspurified by flash column chromatography on silica gel (hexane/AcOEt = 3 : 1) to afford the title compound (37.2 mg, 18% yield) as a pale purple solid.
 

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