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Chemical Structure| 1984-49-2 Chemical Structure| 1984-49-2

Structure of 1984-49-2

Chemical Structure| 1984-49-2

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Product Details of [ 1984-49-2 ]

CAS No. :1984-49-2
Formula : C24H16N2
M.W : 332.40
SMILES Code : C1(NC2=C3C=CC=C2)=C3C=C(C4=CC5=C(C=C4)NC6=C5C=CC=C6)C=C1
MDL No. :MFCD11046470
InChI Key :PUMOFXXLEABBTC-UHFFFAOYSA-N
Pubchem ID :12462601

Safety of [ 1984-49-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H317
Precautionary Statements:P280

Computational Chemistry of [ 1984-49-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 26
Num. arom. heavy atoms 26
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 0.0
Num. H-bond donors 2.0
Molar Refractivity 110.6
TPSA ?

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

31.58 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.68
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

6.48
Log Po/w (WLOGP)?

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

6.62
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.

4.75
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

6.63
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

5.43

Water Solubility

Log S (ESOL):?

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

-6.66
Solubility 0.0000732 mg/ml ; 0.00000022 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.

-6.94
Solubility 0.0000383 mg/ml ; 0.000000115 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

-10.01
Solubility 0.0000000326 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

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

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.

-3.73 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

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<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)

2.03

Application In Synthesis of [ 1984-49-2 ]

* 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 [ 1984-49-2 ]

[ 1984-49-2 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 5408-56-0 ]
  • [ 1984-49-2 ]
  • [ 1338488-87-1 ]
  • 2
  • [ 67515-59-7 ]
  • [ 1984-49-2 ]
  • 4,4'-(9H,9'H-[3,3'-bicarbazole]-9,9'-diyl)bis(3-(trifluoromethyl)benzonitrile) [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h;Inert atmosphere; General procedure: A mixture of 9H,9'H-3,3'-bicarbazole (500 mg, 1.50 mmol), 4-fluoro-2-methylbenzonitrile (450 mg, 3.33 mmol) and K2CO3(0.99 g, 7.2 mmol) in dimethyl sulfoxide (DMSO) (6 mL) was stirredat 140 C for 12 h under nitrogen atmosphere. After cooling to roomtemperature, the mixture was poured into water, filtered and thenpurified by column chromatography over silica gel with CH2Cl2/petroleum ether (1: 1) as eluent to afford a white solid (760 mg,89%).
90% With potassium carbonate; In dimethyl sulfoxide; at 140℃; for 12h; 3,3?-bicarbazole (0.50 g, 1.5 mmol), potassium carbonate (0.99 g, 7.2 mmol), <strong>[67515-59-7]3-trifluoromethyl-4-fluorobenzonitrile</strong> (0.60 g, 3.3 mmol), DMSO 6 ml, 140 Heated at for 12h.After cooling to room temperature and pouring into 200 ml of water, a large amount of solid was precipitated and stirred for 0.5 h. The white solid was obtained by suction filtration and purified by column chromatography to obtain a pale yellow solid with a yield of 90%.
  • 3
  • [ 1984-49-2 ]
  • [ 20651-67-6 ]
  • 9,9'-di-4-n-butylphenyl-9H,9'H-3,3'-bicarbazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
52% With copper; potassium carbonate; In N,N-dimethyl-formamide; at 145℃;Inert atmosphere; 3,3'-Bicarbazole (1.5 g, 4.5 mmol), <strong>[20651-67-6]1-n-butyl-4-iodobenzene</strong> (2.5 mL, 18 mmol), copper powder(1.70 g, 27.1 mmol), and K2CO3 (3.73 g, 27.1 mmol) were dissolved in 10 mL of anhydrous DMF undernitrogen. After heating the mixture at 145 C overnight, the reaction solution was filtered through aplug of celite. The filtered solution was poured into water and extracted with chloroform. The organicswere combined, washed with brine, and dried with sodium sulfate. After solvent removal, the productwas purified via column chromatography with 1:1 (v/v) dichloromethane-hexane as the eluent toyield 1.41 g (2.36 mmol, 52%) of BCz-nBuPh as a white solid. For OLED devices, the product wasfurther purified twice via vacuum sublimation. The sublimation yield was 33%. Mp 146 C. 1H-NMR(400 MHz, CDCl3): delta (ppm) 8.45 (s, 2H), 8.23 (d, J = 7.7 Hz, 2H), 7.77 (dd, J = 8.5 Hz, J = 1.6 Hz, 2H),7.52-7.49 (m, 6H), 7.44-7.42 (m, 8H), 7.32-7.30 (m, 2H), 2.76 (d, J = 7.6 Hz, 4H), 1.77-1.69 (m, 4H),1.51-1.42 (m, 4H), 1.01 (t, J = 7.3 Hz, 6H). 13C-NMR (100 MHz, CDCl3): delta(ppm) 142.3, 141.5, 140.2,135.2, 134.3, 129.8, 126.9, 126.0, 125.8, 123.9, 123.5, 120.4, 119.8, 118.9, 110.1 101.0, 35.4, 33.7, 22.5, 14.1.Anal. calcd. for C44H40N2 (%): C, 88.55; H, 6.76; N, 4.69; found: C, 88.07; H, 7.00; N, 4.80%.
 

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