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Chemical Structure| 20474-15-1 Chemical Structure| 20474-15-1

Structure of 20474-15-1

Chemical Structure| 20474-15-1

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Product Details of [ 20474-15-1 ]

CAS No. :20474-15-1
Formula : C25H19N
M.W : 333.43
SMILES Code : C12=CC=CC=C1C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=C(C=CC=C5)N2
MDL No. :MFCD28127357
InChI Key :HWTHOPMRUCFPBX-UHFFFAOYSA-N
Pubchem ID :13293432

Safety of [ 20474-15-1 ]

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

Computational Chemistry of [ 20474-15-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 24
Fraction Csp3 0.04
Num. rotatable bonds 2
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 110.79
TPSA ?

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

12.03 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

3.26
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

6.59
Log Po/w (WLOGP)?

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

5.75
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.

5.56
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

5.91
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.41

Water Solubility

Log S (ESOL):?

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

-6.61
Solubility 0.0000818 mg/ml ; 0.000000245 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.

-6.64
Solubility 0.000076 mg/ml ; 0.000000228 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

-10.23
Solubility 0.0000000196 mg/ml ; 0.0000000001 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

High
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.

-3.65 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

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)

3.44

Application In Synthesis of [ 20474-15-1 ]

* 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 [ 20474-15-1 ]

[ 20474-15-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 5394-23-0 ]
  • [ 20474-15-1 ]
  • 4,7-di-(9,9-diphenylacridine-N-yl)-1,10-phenanthroline [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% 2.33 g of 9,9-diphenylacridine,240 mg of 70% oil dispersion of sodium hydride and.20 ml of tetrahydrofuran was added to 50 ml.Liter single-ended round-bottomed flask,After refluxing under argon for 30 minutes, 0.75 g was added.4,7-dichloro-1,10 phenanthroline,Then refluxed at 60 C for 24 hours,After cooling to room temperature, saturated saline was quenched,Extracted with dichloromethane, and dried over anhydrous sodium sulfate.The organic phase was filtered and dried. A methanol: dichloromethane volume ratio of 1:30 to obtain the product 2.15 grams. White solid, Yield.85%
  • 2
  • [ 5394-23-0 ]
  • [ 20474-15-1 ]
  • 3,8-bis-(9,9-diphenylacridine-N-yl)-1,10-phenanthroline [ No CAS ]
YieldReaction ConditionsOperation in experiment
80% .33 g of 9,9-diphenylacridine, 240 mg of 70% oil-dispersed sodium hydride and 20 ml of tetrahydrofuran were added to 50 mlLiter single-necked round-bottomed flask, under reflux under an argon atmosphere for 30 minutes, was added 0.75 g of 3,8-dichloro-1,10 phenanthroline,60 C for 24 hours, cooled to room temperature, quenched with saturated brine, extracted with dichloromethane, dried over anhydrous sodium sulfateThe organic phase was filtered and dried. The product was 2.03 g in a ratio of methanol: dichloromethane 1:20 by volume. White solid, Yield.80%.
  • 3
  • [ 52333-42-3 ]
  • [ 20474-15-1 ]
  • C32H22N4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
94% With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate; In toluene; at 110.0℃; for 48.0h; (2) A mixture of intermediate 2 (1.0 g, 4.76 mmol), 9,9-diphenylacridine (1.75 g, 5.24 mmol), sodium tert-butoxide (0.63 g, 6.56 mmol), palladium acetate (0.025 g, 0.11 mmol), tri-tert-butylphosphine tetrafluoroborate (0.095 g, 0.33 mmol), and toluene 45 mL were charged together into a 100 mL round bottom flask. Refluxed at 110C for 48 hours. The reaction was then quenched with 10 mL of saturated aqueous sodium chloride. After extraction with dichloromethane, dried over anhydrous sodium sulfate. Finally, silica gel column chromatography was carried out using dichloromethane / petroleum ether (v / v = 3: 2) as the eluent to obtain compound 4. Yield: 94%.
  • 4
  • [ 20474-15-1 ]
  • [ 171408-84-7 ]
  • 2,7-bis(9,9-diphenylacridin-10(9H)-yl)-9,9'-spirobi[fluorene] [ No CAS ]
YieldReaction ConditionsOperation in experiment
84% With tri-tert-butyl phosphine; palladium diacetate; sodium t-butanolate; In tetrahydrofuran; toluene; at 110℃; for 8h;Inert atmosphere; A mixture of <strong>[171408-84-7]2,7-dibromo-9,9'-spirobi[fluorene]</strong> (SP, 1 g, 1 equiv.), 9,9-diphenyl-9,10 dihydroacridine(1, 1.50 g, 2.1 equiv.), Pd(OAc)2 (0.05 g, 0.1 equiv.), t-Bu3P (10% in toluene, 0.15 mL, 0.03 equiv.), NaOt-Bu(0.81 g, 4 equiv.), anhydrous toluene (80 mL), and dry THF (20 mL) were added together and stirredunder a nitrogen atmosphere for 8 h at 110 C. After completion of the reaction, the crude mixture wasextracted with dichloromethane and water. The organic layer was dried over anhydrous sodium sulphateand concentrated through a rotary evaporation process. The residue was purified by using silica columnchromatography with a n-hexane:dichloromethane (4:1) solvent system to achieve SP1 as a white solid.Yield: 84%; 1H-NMR (CDCl3) delta 7.96-7.98 (d, J = 10 Hz, 2H), 7.74-7.76 (d, J = 10 Hz, 2H), 7.31-7.35 (t, J = 10Hz, 2H), 7.15-7.20 (m, 16H), 6.90-6.98 (m, 18H), 6.79-6.81 (m, 6H), 6.59 (s, 2H), 6.26-6.28 (d, J = 10 Hz, 2H);13C NMR (500MHz, CDCl3) delta 151.91, 147.58, 146.57, 142.14, 141.90, 140.82, 140.75, 130.75, 130.40, 130.10,129.42, 128.16, 128.08, 127.63, 127.57, 126.81, 126.26, 123.62, 122.30, 120.30, 120.15, 114.06, 56.68; GC-MS:978.58 for C75H50N2 [M+ H+].
  • 5
  • [ 2050-48-8 ]
  • [ 20474-15-1 ]
  • C62H44N2O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% The 4-benzoyl-4'-bromobiphenyl (0.11 g, 0.3 mmol), 9, 10 - dihydro - 9, 9 - diphenyl acridine (0.23 g, 0 . 66 mmol), tri-tert-butylphosphonium tetrafluoroboronate (0.02 g), sodium tert-butoxide(0.2 g) adding 100 ml three-neck bottle in, vacuum replace the nitrogen three times, added into the dry toluene after 20 ml. Stir at room temperature 15 min, adding Pd2(dba)3(0.02 G), 120 C under stirring 18 h. Ling actually to the room temperature, over-elution column (for eluting DCM), turns on lathe does, [...] powder sample, carrying out column chromatography separation, to obtain white solid 0.21 g (Y=79%).
 

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