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Chemical Structure| 1221237-87-1 Chemical Structure| 1221237-87-1

Structure of 1221237-87-1

Chemical Structure| 1221237-87-1

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Product Details of [ 1221237-87-1 ]

CAS No. :1221237-87-1
Formula : C24H17N
M.W : 319.40
SMILES Code : N1(C2=CC(C3=CC=CC=C3)=CC=C2)C4=C(C5=C1C=CC=C5)C=CC=C4
MDL No. :MFCD28167065
InChI Key :LKXFMLDAUIXMGY-UHFFFAOYSA-N
Pubchem ID :58722663

Safety of [ 1221237-87-1 ]

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

Computational Chemistry of [ 1221237-87-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 25
Fraction Csp3 0.0
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 0.0
Molar Refractivity 106.22
TPSA ?

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

4.93 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.52
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

6.62
Log Po/w (WLOGP)?

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

6.45
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.

5.51
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

5.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.54

Water Solubility

Log S (ESOL):?

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

-6.6
Solubility 0.0000804 mg/ml ; 0.000000252 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.

-6.52
Solubility 0.0000955 mg/ml ; 0.000000299 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

-9.15
Solubility 0.000000228 mg/ml ; 0.0000000007 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

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

Yes
Log Kp (skin permeation)?

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

-3.55 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<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)

2.14

Application In Synthesis of [ 1221237-87-1 ]

* 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 [ 1221237-87-1 ]

[ 1221237-87-1 ] Synthesis Path-Downstream   1~20

YieldReaction ConditionsOperation in experiment
90% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In toluene; at 110.0℃; for 12.0h;Inert atmosphere; General procedure: 22.42 g (54.88 mmol) of compound J,Bromo-4,6-diphenylpyridine, 20.43 g (65.85 mmol) of compound B and 7.92 g (82.32 mmol) of sodium tert-butoxide were dissolved in 400 ml of toluene,1.65 g (1.65 mmol) of dibenzylidenepalladium and 1.78 g (4.39 mmol) of tri-t-butylphosphine were added thereto in a dropwise manner.Under nitrogen flow,The reaction solution was heated and stirred at 110 C for 12 hours.When the reaction is complete,The solid obtained by pouring methanol into the reactant was filtered and redissolved in chlorobenzene, activated carbon and anhydrous magnesium sulfate were added thereto, and the mixture was stirred. The solution was filtered and recrystallized by using chlorobenzene and methanol to obtain 28.10 g (80%) of compound B-10.
  • 2
  • [ 870119-42-9 ]
  • [ 98-80-6 ]
  • [ 1221237-87-1 ]
  • 3
  • [ 86-74-8 ]
  • [ 1221237-87-1 ]
  • 4
  • [ 1121-86-4 ]
  • [ 1221237-87-1 ]
  • 5
  • [ 1221237-87-1 ]
  • 9-([1,1′-biphenyl]-3-yl)-3-bromo-9H-carbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
90% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 12.0h;Reflux; 20 g (62.6 mmol) of compound K were suspended in 200 ml of DMF,To this was added 12.93 g (72.67 mmol) of NBS little by little,And the mixture was refluxed and stirred for 12 hours.then,Add distilled water to complete the reaction,The mixture was extracted with dichloromethane,And the organic layer thus obtained was filtered through silica gel.Then,After removing the organic solution,The solid product was subjected to silica gel column separation with hexane: dichloromethane = 7: 3 (v / v)Recrystallization from methylene chloride and n-hexane,22.4 g (90%) of compound L was obtained.
88% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20.0℃; for 12.0h; 37 g (114 mmol) of the compound 9- (biphenyl-3-yl) -9H-carbazole and 22 g (126 mmol) of NBS were suspended in 600 mL of dimethylformamide, followed by stirring at room temperature for 12 hours. The reaction solution was added as distilled water and stirred at room temperature for 6 hours. The filtrate was filtered under reduced pressure, the solid was added to methyl alcohol and stirred at room temperature again. After filtration under reduced pressure, compound 9- (biphenyl-3-yl) -3-bromo-9H-carbazole, 40g (yield: 88%) was obtained.
88% With N-Bromosuccinimide; In N,N-dimethyl-formamide; for 12.0h;Cooling with ice; Darkness; Compound 2-46-6 (19.1 g, 60 mmol) and 100 mL of N,N-dimethylformamide were added into a 250 mL single-necked flask, and 60 mmol N,N-dimethylformamide of NBS was added dropwise in an ice bath. The solution was reacted under stirring for 12 hours in the dark, and then the reaction was ended. The reaction solution was poured into 500 mL of water, filtered with suction, and the filter residue was recrystallized, with a yield 88%. http://baike.sogou.com/lemma/ShowInnerLink.htm?lemmaId=600024&ss_c=ssc.citiao.link
With N-Bromosuccinimide; In chloroform; for 5.0h;Reflux; <strong>[1221237-87-1]9-(biphenyl-3-yl)-9H-carbazole</strong> (16.2 g, 50.7 mmol) was dissolved in chloroform (320 mE), and N135 (9.03 g, 50.7 mmol) was slowly dropped. The mixture was refluxed and stirred for 5 hours. After completion of the reaction, distilled water was added and extracted. The resultant was colunmed in the silica-gel such that crude-state 9-(biphenyl-3-yl)-3-bromo-9H-carbazole (17.2 g) was obtained.
40 g With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20.0℃; for 12.0h; Compound 9- (biphenyl-3-yl) -9H-carbazole 37g (114 mmol),22 g (126 mmol) of N-Bromosuccinimide (NBS) were dissolved in dimethylformamideAnd the mixture was stirred at room temperature for 12 hours.Add the reaction mixture to distilled water and stir at room temperature for 6 hours.The filtrate is filtered under reduced pressure, the solid is dissolved in methyl alcohol, and the mixture is stirred at room temperature.After filtration under reduced pressure,9- (biphenyl-3-yl) -3-bromo-9H-carbazole, 40 g.

  • 6
  • [ 1221237-87-1 ]
  • 9-(biphenyl-3-yl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole [ No CAS ]
  • 7
  • [ 1221237-87-1 ]
  • C42H26N2 [ No CAS ]
  • 8
  • [ 185112-61-2 ]
  • [ 98-80-6 ]
  • [ 1221237-87-1 ]
YieldReaction ConditionsOperation in experiment
82% With Pd(pph3)Cl4; potassium carbonate; In ethanol; toluene; for 12.0h;Reflux; 3-bromo-phenylcarbazole (20 g, 62 mmol), phenyl boronic acid (9.08 g, 74 mmol), Pd(pph3)C14 (0.7 g, 0.621 mmol) and K2C03 (17.2 g, 124 mmol) were dissolved in a mixture of ethyl alcohol (200 mE) and toluene (800 mE). The mixture was refluxed and stirred for 12 hours. The resultant was re-precipitated to obtain 9-(biphenyl-3-yl)-9H- carbazole (16.2 g, yield: 82%).
  • 9
  • [ 1221237-87-1 ]
  • C54H34N2O [ No CAS ]
  • 10
  • [ 1221237-87-1 ]
  • C54H34N2O [ No CAS ]
  • 11
  • [ 1221237-87-1 ]
  • (9-([1,1′-biphenyl]-3-yl)-9H-carbazol-3-yl)boronic acid [ No CAS ]
  • 12
  • [ 1221237-87-1 ]
  • 2-(9-(biphenyl-3-yl)-9H-carbazol-3-yl)-5H-benzofuro[3,2-c]carbazole [ No CAS ]
  • 13
  • [ 1221237-87-1 ]
  • C54H34N2 [ No CAS ]
  • 14
  • [ 1221237-87-1 ]
  • C53H33N3 [ No CAS ]
  • 15
  • [ 2113-57-7 ]
  • [ 86-74-8 ]
  • [ 1221237-87-1 ]
YieldReaction ConditionsOperation in experiment
75% With 18-crown-6 ether; copper; potassium carbonate; In 1,2-dichloro-benzene; at 150.0℃; for 24.0h;Inert atmosphere; Compound (2-46-1) (16.7 g, 100 mmol) and Compound (2-46-5) (24.5 g, 105 mmol), copper powder (0.65 g, 10 mmol), potassium carbonate (13.8 g, 100 mmol) and 18-crown-6 (2.65 g, 5 mmol) and o-dichlorobenzene (200 mL) were added to a 500 mL two-necked flask under nitrogen atmosphere, and the solution was heated to 150 C. and reacted under stirring for 24 hours, and then the reaction was ended. The reaction solution was distilled under reduced pressure to remove most of the solvent, and then dissolved with dichloromethane and washed with water for 3 times. The organic solution was collected, mixed with silica gel, and purified by column chromatography, with a yield of 75%.
60 g With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 12.0h;Reflux; Carbazole 50g (299 mmol),3-methabromobiphenyl 60 g (350 mmol) of sodium tertiary butoxide 86g (897 mmol),Tris (dibenzylideneacetone) dipalladium (0) (Pd 2 (dba) 3) 14 g(359 mmol), tri-tert-butylphosphine15 ml (30 mmol) was dissolved in 1000 ml of xyleneAnd the mixture was refluxed for 12 hours.Extraction is carried out with dichloromethane and distilled water, and the organic layer is subjected to silica gel filtration.The organic solution was removed and the residue was subjected to silica gel column chromatography 9- (biphenyl-3-yl) -9H-carbazole, 60g
  • 17
  • [ 1221237-87-1 ]
  • 9-([1,1'-biphenyl]-3-yl)-9’-([1,1'-biphenyl]-4-yl)-9H,9'H-3,3'-bicarbazole [ No CAS ]
  • 18
  • [ 1221237-87-1 ]
  • C30H20N2O2 [ No CAS ]
  • 19
  • [ 1221237-87-1 ]
  • C30H20N2 [ No CAS ]
  • 20
  • [ 1221237-87-1 ]
  • C42H28N2 [ No CAS ]
 

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