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Chemical Structure| 1313514-53-2 Chemical Structure| 1313514-53-2

Structure of 1313514-53-2

Chemical Structure| 1313514-53-2

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Product Details of [ 1313514-53-2 ]

CAS No. :1313514-53-2
Formula : C24H15Br
M.W : 383.28
SMILES Code : BrC1=CC(C2=CC=C3C4=CC=CC=C4C5=CC=CC=C5C3=C2)=CC=C1
MDL No. :MFCD28384139
InChI Key :KWXFBIBEVROWEF-UHFFFAOYSA-N
Pubchem ID :58472032

Safety of [ 1313514-53-2 ]

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

Computational Chemistry of [ 1313514-53-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 24
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 112.1
TPSA ?

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

0.0 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.72
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

7.81
Log Po/w (WLOGP)?

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

7.58
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.

6.75
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

7.26
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.62

Water Solubility

Log S (ESOL):?

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

-7.78
Solubility 0.00000635 mg/ml ; 0.0000000166 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.

-7.66
Solubility 0.00000847 mg/ml ; 0.0000000221 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

-10.73
Solubility 0.0000000072 mg/ml ; 0.0 mol/l
Class?

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

Insoluble

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

Yes
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

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.

-3.09 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

1.0
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

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<2.0
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)

2.38

Application In Synthesis of [ 1313514-53-2 ]

* 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 [ 1313514-53-2 ]

[ 1313514-53-2 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 591-18-4 ]
  • [ 890042-13-4 ]
  • [ 1313514-53-2 ]
YieldReaction ConditionsOperation in experiment
96% With palladium diacetate; sodium carbonate; triphenylphosphine; In water; toluene; for 7h;Inert atmosphere; Reflux; 4,4,5,5-tetra-methyl-2-(triphenylene-2-yl) 1,3,2-dioxaborolan 7.08g (20.0mmol), m- bromoiodobenzene16.97g (60.0mmol) , palladium acetate 135 mg (0.60 mmol), triphenylphosphine629 mg (2.40 mmol), sodium carbonate 4.24 g (40.0 mmol), was mixed1,2-dimethoxyethane 100 mL, water 50 mL, under nitrogen atmosphere, 7 It washeated to reflux time. After the reaction, the organic layer was extracted byadding water and ethyl acetate. The organic layer was concentrated underreduced pressure, silica gel column chromatography (developing solvent:toluene) to remove origin ingredients. The solvent was evaporated under reducedpressure, and the resulting solid was dissolved in a small amount of methylenechloride, solid was precipitated with the addition of methanol. The solid wasfiltered, methanol, to give 7.33g of the synthetic intermediate 2 bysequentially washed with hexane (96% yield).
95% With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In water; toluene; for 8h;Reflux; Inert atmosphere; (B-2) Synthesis of intermediate B Under an argon atmosphere, 3.54 g of triphenylene-2-boronic acid piconal ester, 2.83 g of 3-bromoiodebenzene, 0.231 g of tetrakis(triphenylphosphine)palladium (0), 40 mL of toluene and 20 mL of a 2M sodium carbonate aqueous solution were placed in a flask, and refluxed with stirring for 8 hours. After cooling to room temperature, the reaction solution was extracted with toluene. An aqueous phase was removed, and an organic phase was washed with water and saturated brine sequentially, and then dried with magnesium sulfate. Magnesium sulfate was filtered out, and then the organic phase was concentrated. The resulting residue was purified by means of a silica gel column chromatography to obtain 3.64 g (95%) of an intermediate B.
  • 2
  • [ 870119-58-7 ]
  • [ 1313514-53-2 ]
  • 9-[3'-(2-triphenylenyl)[1,1'-biphenyl]-3-yl]-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
42% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); In water; toluene; for 12h;Reflux; Inert atmosphere; A solution of <strong>[870119-58-7]9-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-9H-carbazole</strong> (5.0 g, 13.5 mmol), 2-(3-bromophenyl)triphenylene (4.2 g, 10.8 mmol), Pd2(dba)3 (0.20 g, 0.22 mmol), SPhos (0.36 g, 0.87 mmol) and K3PO4 (9.2 g, 43.3 mmol) in toluene (100 ml) and water (10 ml) was refluxed under nitrogen for 12 h. After cooling to room temperature, it was diluted with water and extracted with DCM. The combined organic extracts were washed with brine and dried over MgSO4. Upon evaporation off the solvent, the residue was purified by column chromatography on silica gel with hexane/DCM (9/1 to 7/1, v/v) as eluent. The crude product was redissolved in boiling toluene and filtered through a short plug of silica gel topped with MgSO4 to yield Compound 1 (2.5 g, 42%) as a white solid.
  • 3
  • [ 108-36-1 ]
  • [ 654664-63-8 ]
  • [ 1313514-53-2 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; at 65℃; for 18h; 1,3-dibromobenzene (1.6g, 0.010mol) in triphenylen-2-ylboronic acid (3.3g, 0.012mol) into the Preparation 1-7 Synthesized in the same manner as used to obtain the Intermediate 9-1> 2.7g (yield 71%).
  • 4
  • [ 890042-13-4 ]
  • [ 108-36-1 ]
  • [ 1313514-53-2 ]
YieldReaction ConditionsOperation in experiment
60% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; at 90℃; 1,3-dibromobenzene (20.10 g, 85.45 mmol), the starting material,Was dissolved in THF (300 ml) in a round bottom flask, 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -1,3,2-dioxaborolane(33.32 g, 94.05 mmol), Pd (PPh3) 4 (3.95 g, 3.42 mmol), K2CO3 (35.45 g, 256.51 mmol) and water (150 ml) were added and stirred at 90 [deg.] C.After completion of the reaction, the reaction mixture was extracted with CH 2 Cl 2 and water. The organic layer was dried over MgSO 4 and concentrated. The resulting compound was purified by silicagel column and recrystallized19 to obtain Sub 2-59 (yield: 60%).
 

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