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Chemical Structure| 1161009-88-6 Chemical Structure| 1161009-88-6

Structure of 1161009-88-6

Chemical Structure| 1161009-88-6

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Product Details of [ 1161009-88-6 ]

CAS No. :1161009-88-6
Formula : C25H15Br
M.W : 395.29
SMILES Code : BrC1=CC=CC(C23C4=C(C5=C3C=CC=C5)C=CC=C4)=C1C6=C2C=CC=C6
MDL No. :MFCD16660920
InChI Key :GQXFSXMUBDPXBG-UHFFFAOYSA-N
Pubchem ID :68018887

Safety of [ 1161009-88-6 ]

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

Computational Chemistry of [ 1161009-88-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 24
Fraction Csp3 0.04
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 110.44
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.

3.76
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

7.07
Log Po/w (WLOGP)?

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

6.79
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.

6.66
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

7.24
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

6.31

Water Solubility

Log S (ESOL):?

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

-7.43
Solubility 0.0000148 mg/ml ; 0.0000000373 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.

-6.89
Solubility 0.0000512 mg/ml ; 0.000000129 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

-10.98
Solubility 0.0000000042 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

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.

-3.69 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

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<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)

4.0

Application In Synthesis of [ 1161009-88-6 ]

* 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 [ 1161009-88-6 ]

[ 1161009-88-6 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 56525-79-2 ]
  • [ 1161009-88-6 ]
  • 3,6-diphenyl-9-{9,9'-spirobi[fluorene]-5-yl}-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
66% With rubidium carbonate; tri-tert-butyl phosphine; palladium diacetate; In 5,5-dimethyl-1,3-cyclohexadiene; for 24h;Reflux; 4-bromo-spiro-9,9'-spirobifluorene , <strong>[56525-79-2]3,6-diphenyl-9-H-carbazole</strong> and 29. 2g Rb2CO3 suspended in 250mL of xylene. To the suspension to provide 0. 95g (4. 2mmol) Pd(OAc) 2 and 12. 6ml 1M The butylphosphine solution. The mixture was stirred under reflux for 24 hours. After cooling, the organic phase was separated,150mL of water three times, and then concentrated to dryness in vacuo. The residue was extracted with hot toluene, recrystallized three times from toluene,Then sublimation under high vacuum. The yield was 19. 6g (30. 9mmol), corresponding to 66percent of the theoretical value. Purity according to HPLCIt was 99.9percent.
66% With rubidium carbonate; tri-tert-butyl phosphine; palladium diacetate; In para-xylene; for 24h;Reflux; 19.2 g (47 mmol) 4-Brom-9-spirobifluorene, 15 g (47 mmol) 3,6-Diphenyl-9-H-carbazole and 29.2 g Rb2CO3 are suspended in 250 mL p-Xylol. To the suspension are given 0.95 g (4.2 mmol) Pd(OAc)2 and 12.6 ml of a 1M solution of Tri-tert-butylphosphine. The mixture is stirred 24 h under reflux. After cooling the organic phase is separated, washed three times with 150 mL water and is subsequently concentrated to dryness in vacuo. The residue is hot extracted with toluene, recrystallized three times from toluene and subsequently sublimated at high vacuum. Yield is 19.6 g (30.9 mmol) corresponding to 66percent of theory. Purity is according to HPLC 99.9percent.
  • 2
  • [ 1161009-88-6 ]
  • [ 18628-07-4 ]
  • C49H30N2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% With tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; In toluene; for 12h;Inert atmosphere; Reflux; The compound 4-bromo-9.9-spirobifluorene (11.94g, 30mmol) and 3,9-bicarbazole (9.99g, 30mmol) were added to a three-necked flask, stirred and dissolved with 300 mL of toluene, protected with nitrogen, and then added. Pd (dba) 2 862.5 mg, 1.5 mmol) and sodium tert-butoxide (5.76 g, 60 mmol), followed by 10 mL of a 10% solution of tri-tert-butylphosphine in toluene. The reaction solution was stirred and refluxed for 12 hours, cooled, and the reaction mixture was washed three times with 100 ml of water.Dry over anhydrous sodium sulfate and then remove the solvent by evaporation.The residue was purified by hydrazine/PE (1:10) through a column.The white solid was obtained as Compound 4 (9.30 g, yield 48%).
 

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[ 1161009-88-6 ]

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