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Chemical Structure| 54381-08-7

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Product Details of [ 54381-08-7 ]

CAS No. :54381-08-7
Formula : C12H10N2O3
M.W : 230.22
SMILES Code : OC1=CC=C(NC2=CC=CC=C2[N+]([O-])=O)C=C1
MDL No. :MFCD00239470
InChI Key :HSDSBIUUVWRHTM-UHFFFAOYSA-N
Pubchem ID :3846708

Safety of [ 54381-08-7 ]

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

Computational Chemistry of [ 54381-08-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 66.83
TPSA ?

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

78.08 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.78
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

3.3
Log Po/w (WLOGP)?

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

3.04
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.

1.6
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

0.02
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.95

Water Solubility

Log S (ESOL):?

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

-3.67
Solubility 0.0491 mg/ml ; 0.000213 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.

-4.62
Solubility 0.00558 mg/ml ; 0.0000242 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

-3.78
Solubility 0.0383 mg/ml ; 0.000166 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

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.

-5.36 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

3.0 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)

2.59

Application In Synthesis of [ 54381-08-7 ]

* 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 [ 54381-08-7 ]

[ 54381-08-7 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 54381-08-7 ]
  • 4-(2-Amino-phenylamino)-phenol; hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
82.2% Procedure: A, B, C and D placed in a 2 liter 3 neck flask equipped with a stirrer and a reflux condenser. The reaction is heated by means of a heating mantle, with stirring, to reflux (about 115 C) for 23 hours. The reaction is allowed to cool to room temperature and the resulting mixture filtered. Solid that is obtained is a salt residue and is discarded. The filtrate is evaporated of solvent on a rotary evaporator. The resulting solid is recrystallized from aqueous ethanol (50/50). Weight of pure product obtained = 189 g. m.p. = 144-145.5 C., % yield = 82.2%.
75% Procedure: A, B, C and D are mixed in a small autoclave and heated to 170-180 C for 28 hours. The reaction mixture was then cooled and filtered. The filtrate was evaporated of solvent on a rotovac and the resulting solid was recrystallized from a mixture of ethanol and water (50/50). 33.3 grams (75% yield) of a red brown crystalline material was obtained having a melting point in a range of 140-141 C.
  • 4
  • [ 2082-59-9 ]
  • [ 54381-08-7 ]
  • [ 141798-56-3 ]
  • [ 123-30-8 ]
  • [ 88-73-3 ]
  • 2-Butyl-3-(4-hydroxyphenyl)benzimidazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride;palladium-carbon; In methanol; dimethyl sulfoxide; ethyl acetate; Preparation 14 2-Butyl-3-(4-hydroxyphenyl)benzimidazole A mixture of (8.0 g, 51 mmol, 1.0 eq) 1-chloro-2-nitrobenzene and (5.54 g, 51 mmol, 1.0 eq) 4-aminophenol in 40 ml of dry dimethylsulfoxide was heated to reflux for 18 hours. The reaction mixture was cooled, poured into 400 ml of 0.1N HCl and 400 ml ethyl acetate, stirred, and filtered through celite. The filtrate layers were separated, and the aqueous layer was extracted with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over MgSO4, and concentrated to give 8 g of a dark oil. Silica gel chromatography eluding with 20% ethyl acetate/hexane gave 1.63 g, 14%, of a red solid. A mixture of (1.6 g, 6.89 mmol, 1.0 eq) <strong>[54381-08-7]4-N-(2-nitrophenyl)amino phenol</strong> and 800 mg of 10% Pd/C in 100 ml ethyl acetate was placed on a Parr hydrogenation apparatus and shaken under 50 psi H2 for 3 hours. The mixture was filtered through celite, concentrated in vacuo , and chromatographed on a silica gel column eluding with 50% ethyl acetate/hexane to give 1.3 g, 94%, of an orange-yellow solid. A mixture of (600 mg, 3.00 mmol, 1.0 eq) 4-N-(2-aminophenyl)amino phenol and 10 ml valeric anhydride was heated to reflux for 18 hours. The mixture was taken up in 50 ml of methanol, basified with 2N NaOH to pH 10, and stirred 1 hour at room temperature. The reaction mixture was then neutralized and extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over MgSO4 and concentrated to give 1 g of an oil. Silica gel chromatography eluding with 21/2% CH3OH-CH2Cl2 gave 124 mg, 16%, solid. M.P.: 192-194C.
  • 5
  • [ 54381-08-7 ]
  • 2-(4-methylbenzenesulfonyl)-4-(2-nitrophenylamino)phenol [ No CAS ]
  • 6
  • [ 54381-08-7 ]
  • 2-(4-methoxybenzenesulfonyl)-4-(2-nitrophenylamino)phenol [ No CAS ]
  • 7
  • [ 54381-08-7 ]
  • 2-(4-chlorobenzenesulfonyl)-4-(2-nitrophenylamino)phenol [ No CAS ]
 

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