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Chemical Structure| 84405-44-7 Chemical Structure| 84405-44-7

Structure of 84405-44-7

Chemical Structure| 84405-44-7

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Product Details of [ 84405-44-7 ]

CAS No. :84405-44-7
Formula : C14H6Br2O2
M.W : 366.00
SMILES Code : O=C1C2=C(C=CC(Br)=C2)C3=CC=C(Br)C=C3C1=O
MDL No. :MFCD03931078
InChI Key :LTZIIBSPYWTOQV-UHFFFAOYSA-N
Pubchem ID :265843

Safety of [ 84405-44-7 ]

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

Computational Chemistry of [ 84405-44-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 18
Num. arom. heavy atoms 12
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 75.94
TPSA ?

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

34.14 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.23
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

3.9
Log Po/w (WLOGP)?

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

4.26
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.

3.15
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

4.86
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.68

Water Solubility

Log S (ESOL):?

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

-5.06
Solubility 0.00319 mg/ml ; 0.00000872 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.

-4.32
Solubility 0.0177 mg/ml ; 0.0000484 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

-6.9
Solubility 0.0000465 mg/ml ; 0.000000127 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

No
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

Yes
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.

-5.76 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

0.0
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.

2.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

1.0 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)

2.53

Application In Synthesis of [ 84405-44-7 ]

* 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 [ 84405-44-7 ]

[ 84405-44-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 84405-44-7 ]
  • [ 4506-66-5 ]
  • 2,7,13,18-tetrabromodibenzo[a,c]dibenzo[5,6:7,8]quinoxalino-[2,3-i]phenazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With acetic acid; triethylamine; In ethanol; at 100 - 130℃; for 6h;Inert atmosphere; 2,7-DBPD (0.76 g, 2.1 mmol), and benzene-1,2,4,5-tetraamine tetrahydrochloride (0.28 g, 1.0 mmol) were transferred into a roundbottom flask and suspended in 6 ml of ethanol and 20 ml of acetic acid to make a brown suspension in an Ar atmosphere with stirring, and heated to 100 °C. After theaddition of 1.0 ml of triethylamine, the mixture immediately changed to a redcolour, and was further refluxed at 130 °C for 6 h. Once cooled to room temperature, the mixture was diluted with acetic acid and poured into 200 ml of water. The redprecipitate was collected and exhaustively washed by soxhlet extraction with water,ethanol, chloroform, THF, N,N-dimethylformamide and ethanol again, and dried at120 °C overnight to yield 2-TBQP as a copper-coloured powder in quantitative yield.Elemental analysis (percent): calculated for (C34H14Br4N4): C, 51.16, H, 1.77, N, 7.02, Br,40.05; found: C, 50.72, H, 2.05, N, 7.11, Br 39.93. High-resolution mass spectrometry(negative mode) m/z = 797.7895 (Supplementary Fig. 4), calculated forC34H14Br4N4, 797.7911; no solution NMR data were collected because of 2-TBQP?spoor solubility. Its structure was confirmed with single-crystal XRD analysis.
With acetic acid; triethylamine; In ethanol; at 100 - 130℃; for 6h;Inert atmosphere; 2,7Dibromophenanthrene-9,10-dione (2,T-DBPD, 0.76 g, 2.1 nimo) andbenzene-1 ,2,4,54etraamine tetrahydrochbride (0.28 g, 1.0 mmo) were transferred into a round bottom flask with a magnetic spin bar, and suspended in mL of ethano and 20 mL of acetic acid to make a brown suspension in Ar atmosphere, andheated to 100°C. After the addition of 1.0 mL of triethybmine, the mixture immediat&y changed to red coor, and was further refluxed at 130°C for 6 hours. Once co&ed to room temperature, the mixture was dNuted with acefic acid and poured into 200 mL of water. The red precipitate was coNected and exhaustiv&y washed by soxHet extraction with water, ethano, chloroform, THF, N,N dmethylformamide and ethano again, and dried at 120°C overnight in vacuum oven to yield 2TBQP as coppercoored powder. The structure was confirmed with singlecryst& XRD data anaysis. All reagents were obtained from Aldrich
  • 2
  • [ 54523-47-6 ]
  • [ 84405-44-7 ]
  • 5,10-dibromo-1,3-bis(4-bromophenyl)-2H-cyclopenta[l]phenanthren-2-one [ No CAS ]
 

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