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Chemical Structure| 205-25-4 Chemical Structure| 205-25-4

Structure of 205-25-4

Chemical Structure| 205-25-4

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Product Details of [ 205-25-4 ]

CAS No. :205-25-4
Formula : C16H11N
M.W : 217.27
SMILES Code : C1(NC2=C3C=CC=C2)=C3C4=CC=CC=C4C=C1
MDL No. :MFCD00215940
InChI Key :UGFOTZLGPPWNPY-UHFFFAOYSA-N
Pubchem ID :67459

Safety of [ 205-25-4 ]

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

Computational Chemistry of [ 205-25-4 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 17
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 0.0
Num. H-bond donors 1.0
Molar Refractivity 73.31
TPSA ?

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

15.79 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.13
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

4.3
Log Po/w (WLOGP)?

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

4.47
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.

3.68
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

4.61
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.84

Water Solubility

Log S (ESOL):?

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

-4.64
Solubility 0.00502 mg/ml ; 0.0000231 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-4.34
Solubility 0.00982 mg/ml ; 0.0000452 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Moderately 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

-6.64
Solubility 0.0000497 mg/ml ; 0.000000229 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

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

Yes
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.

-4.57 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

0.0
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)

1.22

Application In Synthesis of [ 205-25-4 ]

* 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 [ 205-25-4 ]

[ 205-25-4 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 100-63-0 ]
  • [ 81-16-3 ]
  • [ 205-25-4 ]
  • 3
  • [ 205-25-4 ]
  • [ 1698-16-4 ]
YieldReaction ConditionsOperation in experiment
87% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 0℃; for 24h; Preparation of compound 3-3 [148] After dissolving compound 3-2 (20 g, 92 mmol) in dimethylformamide (DMF) at 0C, N-bromosuccinimide (NBS) (16.3 g, 92 mmol) was slowly added to the reaction mixture and the reaction mixture was stirred for 24 hours. After completing the reaction, the organic layer was extracted EA and was dried with MgSO4 to remove the remaining moisture. The obtained organic layer was separated through column to obtain compound 3-3 (23.5 g, 87 %).
86% With N-Bromosuccinimide; In tetrahydrofuran; at 0 - 20℃; for 12h; The 20.4g (0.1mol) 7H- benzo [c] carbazole was dissolved in tetrahydrofuran (THF, 500mL), and then the resulting solution was stirred at 0 10 minutes. Thereto was added N- bromosuccinimide (NBS, 18.68g, 0.105mol), the resulting mixture was stirred at normal temperature for 12 hours, then extracted with ethyl acetate and distilled water. The organic layer was dried over anhydrous magnesium sulfate (MgSO4) was dried, then the solvent was removed, and subjected to silica gel column chromatography to give 25.4g (86%) Compound B-1.
80% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 24h; After dissolving compound 1-9 (8.7 g, 40.1 mmol) in dimethylformamide (DMF) (50 mL), and adding N-bromosuccinimide (NBS) (4.7 g, 40.1 mmol), the reaction mixture was stirred for a day at room temperature. After terminating the reaction, the reaction mixture was extracted with EA, and the organic layer was concentrated. The resulting product was purified by a silica column to give compound 1-10 (9.5 g, 80 %).
78% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 24h; Preparation of Compound 7-1 [193] 7H-benzo[c]carbazole (50g, 0.23mol) was dissolved in DMF 1.4L, and NBS (41g, 0.23mol) was added, after which the mixture was stirred at room temperature for 24 hours. After termination of the reaction, the resultant mixture was extracted with EA and the organic layer was distilled under reduced pressure. Silica column separation was then performed, yielding Compound 7-1 (53.2g, 78%).
77% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 2h;Inert atmosphere; Cooling with ice; Under nitrogen atmosphere, N-bromosuccinimide (12.6 g) was added to a solution of 7H-benzo [c] carbazole (15.7 g) in N, N-dimethylformamide (250 mL) under ice cooling, and the temperature was raised to room temperature And the mixture was stirred for 2 hours. The resulting reaction solution was extracted with toluene, the toluene layer was washed with saturated brine, dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the objective 10-bromo-7H-benzo [c] carbazole (16.2 g, yield 77%)
39% With N-Bromosuccinimide; In N,N-dimethyl-formamide; at 20℃; for 12h; After introducing 7H-benzo[cjcarbazole (50 g, 230 mmol) and DMF (200 mL) into a flask, the mixture was stirred, and N-bromosuccinimide (42 g, 230 mmol) dissolved in DMF (50 mL) was added thereto. The resultant mixture was stirred at room temperature for 12 hours, and extracted with distilled water and MC. The obtained organic layer was dried with magnesium sulfate, and distilled under reduced pressure. The residue was purified by column chromatography to obtain compound A (10-bromo-7H-benzo[cjcarbazole) (1 6g, yield: 23.5%)
70.8 g With N-Bromosuccinimide; In dichloromethane; at -5 - 0℃; for 3h; D: Add 65.1 g of benzo [c] carbazole and 600 ml of dichloromethane to a clean and dry 1000 mL four-neck reaction flask.Stir until dissolved, then cool to -5 , add 54g NBS in batches, after the addition is complete, hold the reaction at -5-0 for 3h,HPLC followed the completion of the benzo [c] carbazole reaction. After the reaction was completed, 300 ml of clear water was added to the reaction material.After stirring for a period of time, the layers were separated, the organic phase was removed, and the solvent was removed under reduced pressure to obtain a dark brown oil.450 ml of toluene and 3 g of activated carbon were added, and the mixture was stirred under reflux for 1 h, then filtered while hot, and the solvent was removed under reduced pressure from the filtrate.A pale yellow oil was obtained, 90 ml of ethanol was added, and after dissolving, crystallized at room temperature, suction filtration was performed,A white solid was obtained, 70.8 g was obtained by drying, HPLC: 99.27%,

  • 4
  • [ 205-25-4 ]
  • [ 13438-50-1 ]
  • C32H19N [ No CAS ]
YieldReaction ConditionsOperation in experiment
2.17 g With tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine; sodium t-butanolate; In 5,5-dimethyl-1,3-cyclohexadiene; for 8h;Reflux; Inert atmosphere; 3-bromo fluoranthene 3.10g, tris di benzylideneacetone di palladium (0) 0.18g, tri-t-butyl phosphine tetrafluoro hydro borate 0.23g, sodium-t-butoxide1.30g, dehydration xylene 100mL synthesized to the argon atmosphere, the material compound (A) 2.17g, andthe method of the wily idea was injected in the flask and it mixed reflux 8 hours heating The reacting solution was extracted in toluene to theroom temperature after doing the cooling and it filteredcellite. The filter liquor was concentrated and the residue was refined to the silica gel column chromatographyand the yellow entity 2.71g was obtained.
 

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