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Chemical Structure| 23449-08-3 Chemical Structure| 23449-08-3

Structure of 23449-08-3

Chemical Structure| 23449-08-3

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Product Details of [ 23449-08-3 ]

CAS No. :23449-08-3
Formula : C21H14BrN3
M.W : 388.26
SMILES Code : BrC1=CC=C(C2=NC(C3=CC=CC=C3)=NC(C4=CC=CC=C4)=N2)C=C1
MDL No. :MFCD00194632
InChI Key :AYHGAQGOMUQMTR-UHFFFAOYSA-N
Pubchem ID :1728672

Safety of [ 23449-08-3 ]

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

Computational Chemistry of [ 23449-08-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 25
Num. arom. heavy atoms 24
Fraction Csp3 0.0
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 103.83
TPSA ?

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

38.67 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

4.12
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

5.65
Log Po/w (WLOGP)?

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

5.64
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.

4.57
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

5.62
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.12

Water Solubility

Log S (ESOL):?

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

-6.32
Solubility 0.000186 mg/ml ; 0.00000048 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.

-6.23
Solubility 0.000231 mg/ml ; 0.000000594 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

-9.61
Solubility 0.0000000944 mg/ml ; 0.0000000002 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

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.

-4.66 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

1.0
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)

2.37

Application In Synthesis of [ 23449-08-3 ]

* 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 [ 23449-08-3 ]

[ 23449-08-3 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 654664-63-8 ]
  • [ 23449-08-3 ]
  • C39H25N3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
70% With tris-(dibenzylideneacetone)dipalladium(0); triphenylphosphine; sodium t-butanolate; In tetrahydrofuran; toluene;Reflux; triphenylen-2-ylboronic acid (5.4g, 20mmol) was dissolved in a THF 2-(4-bromophenyl)-4,6-diphenyl-1,3,5-triazine (7.8g, 20mmol), Pd2(dba)3 (0.9g, 1mmol), PPh3 (0.5g, 2mmol), followed by the addition of NaOt-Bu (5.8g, 60mmol), toluene (210 mL), stirred and refluxed. When the reaction is complete, the organic layer was dried over MgSO4, and extracted with water and ether and recrystallized silicagel column and the resulting organic compound and then concentrated and compound 5-6 was obtained 7.5g (70% yield).
  • 2
  • [ 1257220-47-5 ]
  • [ 23449-08-3 ]
  • [ 1357066-27-3 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate; copper(l) iodide; (S,S)-1,2-diaminocyclohexane; In toluene; at 100℃;Inert atmosphere; Compound 1 (0.60 g, 2.12 mmol), compound 2 (0.9 g, 2.32 mmol),tripotassium phosphate (0.89 g, 4.19 mmol), copper iodide (8 mg,0.04 mmol), and trans-1,2-diaminocyclohexane (0.21 g, 1.48 mmol)were dissolved in distilled toluene (40 mL), and the reaction mixture was refluxed at 100 C in N2 for 12 h. There after, the reaction mixturewas cooled to 25 C and filtered through Celite. It was concentrated under vacuum. The residue was purified by silica gel column chromatography using dichloromethane (DCM)/hexane (1:5 v/v) as the eluent to give a pure compound 3, which was a white-green solid (1.13 g);yield 90%. mp 255.6 C. IR (KBr, cm-1) ν: 2957, 1604, 1516, 1452,1370, 1219, 838, 772, 692. 1H NMR (CDCl3, 500 MHz, ppm): δ9.02-9.01 (2H, d, J=8.5 Hz), 8.82-8.80 (4H, dd, J=8.3, 1.5 Hz), 8.43(1H, s), 8.20-8.19 (1H, d, J=7.6 Hz), 7.85-7.84 (1H, d, J=7.7 Hz),7.83-7.81 (2H, dd, J=6.7, 1.8 Hz), 7.62 (1H, s), 7.61-7.60 (1H, t,J=1.7 Hz), 7.60-7.58 (3H, d, J=7.3 Hz), 7.57-7.56 (1H, t,J=1.7 Hz), 7.54-7.53 (2H, d, J=8.3 Hz), 7.44-7.40 (2H, m),7.38-7.35 (1H, td, J=7.5, 1.1 Hz), 7.34-7.31 (1H, t, J=7.5 Hz),7.29-7.26 (1H, td, J=7.4, 1.1 Hz), 1.53 (6H, s). 13C NMR (CDCl3,125 MHz, ppm): δ 170.91, 153.36, 153.31, 141.71, 140.86, 140.76,139.56, 136.10, 134.94, 132.80, 132.67, 130.70, 129.01, 128.70,127.07, 126.82, 126.40, 125.81, 124.01, 123.32, 122.56, 120.43,120.26, 119.41, 111.41, 109.92, 104.07, 46.81, 27.94; Uv-Vis (CHCl3) λ max/nm (ε/105 mol-1 dm3 cm-1): 362 (0.24); Found: [M+H]+590.2468; molecular formula C42H30N4 requires [M+H]+ 590.2470.
With potassium tert-butylate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; for 24h;Inert atmosphere; Reflux; Added to the reaction bottle 0.1 µM intermediate 1, 0.1 µM intermediate 2, 20g tert-butanolate, 5g arrowhead three uncles acetate butyl phosphine tetrafluoroborate salts and toluene (1000 ml), under the protection of nitrogen heating reflux for 24 hours, cooling, removing the toluene, adding dichloromethane, washing, drying, the crude product of column, then methylene chloride and ethanol to recrystallize the purified product, compound 5.
  • 3
  • [ 5599-70-2 ]
  • [ 23449-08-3 ]
  • C33H21ClN4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
77% With copper(l) iodide; 1,10-Phenanthroline; potassium hydroxide; In 5,5-dimethyl-1,3-cyclohexadiene; for 4.0h;Inert atmosphere; Reflux; In a nitrogen atmosphereThe compound of formula IA (10 g, 50 mmol) and the compound of formula IB (19 g, 50 mmol)Was added to 250 ml of xylene and potassium hydroxide (5.6 g, 99 mmol), 1,10-phenanthroline (10 g, 19 mmol) was added with stirring.Then, by heating, copper iodide (2.8 g, 15 mmol) was slowly added under reflux. After the reaction was completed for about 4 hours, the reaction was terminated. After completion of the reaction, the temperature was lowered to room temperature, the salt was filtered through a filter, and the organic layer was distilled. Thereafter, the distillate was extracted twice with chloroform and water, and the organic layer was distilled off under reduced pressure Recrystallization with ethanol gave Intermediate 1 (19 g, 77percent).
  • 4
  • [ 3469-20-3 ]
  • [ 23449-08-3 ]
  • C41H28N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; Specific preparation process: 100ml under nitrogenTo the 1,4-dioxane solvent was added <strong>[3469-20-3]2,3-diphenylindole</strong> (1.70 g, 10.0 mmol)And 4-bromotriphenyltriazine (4.27g, 11.0mmol),Tris (dibenzylideneacetone) dipalladium (0.58 g, 0.5 mmol) and tri-tert-butyl phosphorus (15%, 0.15 mmol) were stirred at 110 C for 12 hours.After the reaction was cooled to room temperature, the mixture was filtered through a silica gel funnel, and the solution was concentrated under reduced pressure.The final product (4.90 g, 8.5 mmol) was obtained in a yield of 85%.
 

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