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Chemical Structure| 406482-72-2 Chemical Structure| 406482-72-2

Structure of 406482-72-2

Chemical Structure| 406482-72-2

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Product Details of [ 406482-72-2 ]

CAS No. :406482-72-2
Formula : C19H20BNO2
M.W : 305.18
SMILES Code : N#CC1=CC=C(C2=CC=C(B3OC(C)(C)C(C)(C)O3)C=C2)C=C1
MDL No. :MFCD17015781
InChI Key :UQGDIRDLIFFOHN-UHFFFAOYSA-N
Pubchem ID :11822881

Safety of [ 406482-72-2 ]

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

Computational Chemistry of [ 406482-72-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 23
Num. arom. heavy atoms 12
Fraction Csp3 0.32
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 93.07
TPSA ?

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

42.25 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

0.0
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

4.25
Log Po/w (WLOGP)?

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

3.52
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.

2.28
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

3.47
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.7

Water Solubility

Log S (ESOL):?

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

-4.66
Solubility 0.00662 mg/ml ; 0.0000217 mol/l
Class?

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

Moderately soluble
Log S (Ali)?

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

-4.85
Solubility 0.00432 mg/ml ; 0.0000142 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

-6.59
Solubility 0.0000792 mg/ml ; 0.000000259 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

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

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

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

Yes
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

Yes
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.14 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

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)

3.29

Application In Synthesis of [ 406482-72-2 ]

* 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 [ 406482-72-2 ]

[ 406482-72-2 ] Synthesis Path-Downstream   1~18

  • 3
  • [ 406482-72-2 ]
  • ethyl N-(4'-cyanobiphenyl-4-yl)-5-formylpyrrole-3-glyoxalate [ No CAS ]
  • 4
  • [ 406482-72-2 ]
  • [ 19812-93-2 ]
  • 5
  • 2-(4-bromophenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione [ No CAS ]
  • [ 171364-82-2 ]
  • [ 406482-72-2 ]
  • 6
  • (R)-2,2'-CB012-6,6'-Br-binaphthalene [ No CAS ]
  • [ 406482-72-2 ]
  • C96H90N4O4 [ No CAS ]
  • 7
  • (S)-2,2'-CB012-6,6'-Br-binaphthalene [ No CAS ]
  • [ 406482-72-2 ]
  • C96H90N4O4 [ No CAS ]
  • 8
  • (R)-2,2'-PCH5012-6,6'-Br-binaphthalene [ No CAS ]
  • [ 406482-72-2 ]
  • C104H124N2O4 [ No CAS ]
  • 9
  • (S)-2,2'-PCH5012-6,6'-Br-binaphthalene [ No CAS ]
  • [ 406482-72-2 ]
  • C104H124N2O4 [ No CAS ]
  • 12
  • 4-(tris{4-[2-(trimethylsilyl)ethylsulfanyl]phenyl}methyl)phenyl trifluoromethanesulfonate [ No CAS ]
  • [ 406482-72-2 ]
  • 4-(tris{4-[2-(trimethylsilyl)ethylsulfanyl]phenyl}methyl)-1,1’:4’,1’’-terphenyl-4’’-carbonitrile [ No CAS ]
  • 13
  • [ 406482-72-2 ]
  • [(4’’-cyano-1,1’:4’,1’’-terphenyl-4-yl)methanetriyl]tris(benzene-4,1-diyl)} tris(thioacetate) [ No CAS ]
  • 14
  • 4-bromo-9,9-diphenyl-9,10-dihydroacridine [ No CAS ]
  • [ 406482-72-2 ]
  • 4’-(9,9-diphenyl-9,10-dihydroacridin-4-yl)-[1,1’-biphenyl]-4-carbonitrile [ No CAS ]
  • 16
  • 2-chloro-4-phenyl-6-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,5-triazine [ No CAS ]
  • [ 406482-72-2 ]
  • 4′-(4-phenyl-6-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,5-triazin-2-yl)-[1,1′-biphenyl]-4-carbonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In tetrahydrofuran; water; for 16h;Inert atmosphere; Reflux; A flask was flushed with nitrogen and charged with 6 2-chloro-4-phenyl-6-(3-(9-phenyl-9H-fluoren-9-yl)phenyl)-1,3,5-triazine (10 g, 19.7 mmol), 28 4?-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1?-biphenyl]-4-carbonitrile (6.6 g, 21.7 mmol), 8 Pd(PPh3)4 (0.46 g, 0.39 mmol), and 9 K2CO3 (5.4 g, 39.4 mmol). A mixture of deaerated 10 THF/11 water (13:1, 270 mL) was added and the reaction mixture was heated to reflux under a nitrogen atmosphere for 16 h. After cooling down to room temperature, the THF was removed in vacuo, 12 dichloromethane was added and the organic phase was washed with water three times. Subsequently, the organic phase was dried over Na2SO4 and filtered over a pad of silica. After rinsing with additional dichloromethane, the colorless filtrate was concentrated and 14 n-hexane was added. After stirring for 1 h, the precipitate was collected by suction filtration and washed with n-hexane to yield 12.1 g (94%) of a white solid after drying. Final purification was achieved by sublimation. m/z=651 ([M+H]+).
  • 17
  • 4-(4-bromo-2-(2-methyl-4-(methylsulfonyl)phenyl)-1H-imidazol-5-yl)pyridine [ No CAS ]
  • [ 406482-72-2 ]
  • 4'-(2-(2-methyl-4-(methylsulfonyl)phenyl)-5-(pyridin-4-yl)-1H-imidazol-4-yl)-[1,1'-biphenyl]-4-carbonitrile [ No CAS ]
  • 18
  • [ 1268251-22-4 ]
  • [ 406482-72-2 ]
  • C48H30N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
82% With potassium phosphate; In tetrahydrofuran; water; at 45℃; for 18h;Inert atmosphere; Example of reaction conditions which can be suitably used for preparation of compound of Formula CO from compound of Formula 2 Potassium phosphate K3PO4 (as 10m L aqueous solution, 2 eq.) was degassed with nitrogen for 30 min. THE (41 ml) was also degassed with nitrogen for 30 min. The THF flask was then charged with previously synthesized intermediate of formula 2 (4.5 g, ieq.), 4'-(4,4,5 ,5-tetramethyl-i, 3,2 -dioxaborolan-2 -yl) -[1,1 -biphenyl] -4-carbonitrile (0268) [406482-72-2] (l.ieq.), and palladium source Pdi72 [CAS 1798781-99-3] (0.02 eq.) under a positive nitrogen pressure. The degassed potassium phosphate solution was added, nitrogen purged reflux condenser was attached to the flask and a reaction mixture heated to 45 C with stirring for 18 h. The mixture was allowed to cool down to the room temperature. The precipitate was filtered, washed thoroughly with water. After dissolution in refluxing chlorobenzene and filtration on silicagel layer, the reduction of the solvent afforded white powder that was recrystallzed in loomL chlorobenzene to afford 4.yg (82%) product, m/z 663 [M+H]+.
 

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