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Chemical Structure| 1160294-93-8 Chemical Structure| 1160294-93-8

Structure of 1160294-93-8

Chemical Structure| 1160294-93-8

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Product Details of [ 1160294-93-8 ]

CAS No. :1160294-93-8
Formula : C18H14BrN
M.W : 324.21
SMILES Code : BrC1=CC=C(NC2=CC=C(C3=CC=CC=C3)C=C2)C=C1
MDL No. :MFCD20486764
Boiling Point : No data available
InChI Key :RDSXVQDXXSPFHG-UHFFFAOYSA-N
Pubchem ID :57746339

Safety of [ 1160294-93-8 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P280-P305+P351+P338

Computational Chemistry of [ 1160294-93-8 ] Show Less

Physicochemical Properties

Num. heavy atoms 20
Num. arom. heavy atoms 18
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 89.12
TPSA ?

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

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.27
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

6.5
Log Po/w (WLOGP)?

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

5.86
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.

5.24
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

4.98
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.17

Water Solubility

Log S (ESOL):?

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

-6.41
Solubility 0.000125 mg/ml ; 0.000000386 mol/l
Class?

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

Poorly soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-6.55
Solubility 0.0000916 mg/ml ; 0.000000283 mol/l
Class?

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

Poorly 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

-8.31
Solubility 0.00000158 mg/ml ; 0.0000000049 mol/l
Class?

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

Poorly soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

Low
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

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.

-3.66 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

1.0
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

2.0
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)

2.18

Application In Synthesis of [ 1160294-93-8 ]

* 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 [ 1160294-93-8 ]

[ 1160294-93-8 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1160294-93-8 ]
  • [ 654664-63-8 ]
  • N-(4-(triphenylen-2-yl)phenyl)-[1,1'-biphenyl]-4-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 80℃; for 6h; N- (4-bromophenyl) - [1,1'-biphenyl] -4-amine (3 g, 9.29 mmol)Triphenylene-2-Ylboronic acid (2.53 g, 9.29 mmol),And 2 mol% of tetrakis (triphenylphosphine) palladium were added to tetrahydrofuran (20 ml), potassium carbonate (18.58 mmol)Were dissolved in water (10 ml) and mixed.After stirring at 80 C for 6 hours, the reaction was terminated and the reaction mixture was cooled to room temperature to separate the water and the organic layer. After recovering only the organic layer, anhydrous magnesium sulfate was added and stirred,The mixture was filtered through a silica pad, concentrated under reduced pressure, and purified by column to obtain Intermediate 4-1 (3.54 g, yield 81%).
  • 2
  • [ 870119-58-7 ]
  • [ 1160294-93-8 ]
  • C36H26N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
83.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 110℃; for 24h;Inert atmosphere; Under a nitrogen atmosphere, add 0.01mol 4-bromo-4, -biphenyl-diphenylamine, 0.015mol Z2, 0.02mL 1mol / mL sodium carbonate aqueous solution, 2 × 10-5mol Pd (PPh3) 4 to a 500ml three-necked flask Then, 150ml of toluene-ethanol mixed solvent with a volume ratio of 1.5 to 3.0: 1 was added to dissolve, heated to 110 C, refluxed for 24 hours, and observed the reaction by TLC until the reaction was complete. Naturally cool to room temperature, filter, and spin the filtrate to no fraction. The resulting material was purified through a silica gel column (petroleum ether as eluent) to obtain the target product with a purity of 99.7% and a yield of 83.4%.
83.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; water; toluene; at 110℃; for 24h;Inert atmosphere; Under a nitrogen atmosphere, add 0.01 mol 4-bromo-4, -biphenyl-diphenylamine, 0.015 mol Z2, sodium carbonate aqueous solution, Pd (PPh3) 4 to a 500 ml three-necked flask, and then add 150 ml in a volume ratio of 1.5-3.0 : 1 Dissolve in toluene-ethanol mixed solvent, heat to 110 C, reflux for 24 hours, observe the reaction by TLC until the reaction is complete. Naturally cool to room temperature, filter, and spin the filtrate to no fraction. The resulting material was purified through a silica gel column (petroleum ether as eluent) to obtain the target product with a purity of 99.7% and a yield of 83.4%.
 

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