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Chemical Structure| 78593-33-6 Chemical Structure| 78593-33-6

Structure of 78593-33-6

Chemical Structure| 78593-33-6

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Product Details of [ 78593-33-6 ]

CAS No. :78593-33-6
Formula : C8H5BrN2
M.W : 209.04
SMILES Code : BrC1=CC2=CC=CC=C2N=N1
MDL No. :MFCD01411751
InChI Key :MEYRUXMLXSGXKP-UHFFFAOYSA-N
Pubchem ID :12678051

Safety of [ 78593-33-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H332-H335
Precautionary Statements:P261-P280-P305+P351+P338

Computational Chemistry of [ 78593-33-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 11
Num. arom. heavy atoms 10
Fraction Csp3 0.0
Num. rotatable bonds 0
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 47.24
TPSA ?

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

25.78 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.03
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

1.72
Log Po/w (WLOGP)?

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

2.39
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.

2.15
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

2.65
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

2.19

Water Solubility

Log S (ESOL):?

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

-2.89
Solubility 0.268 mg/ml ; 0.00128 mol/l
Class?

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

Soluble
Log S (Ali)?

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

-1.88
Solubility 2.77 mg/ml ; 0.0133 mol/l
Class?

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

Very 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

-4.19
Solubility 0.0136 mg/ml ; 0.0000652 mol/l
Class?

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

Moderately 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

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.

-6.35 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.

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)

1.81

Application In Synthesis of [ 78593-33-6 ]

* 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 [ 78593-33-6 ]

[ 78593-33-6 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 78593-33-6 ]
  • [ 124-41-4 ]
  • [ 17372-80-4 ]
  • 2
  • [ 78593-33-6 ]
  • [ 17372-79-1 ]
  • 3
  • toluene-4-sulfonic acid-[<i>N</i>'-(3-bromo-cinnolin-4-yl)-hydrazide] [ No CAS ]
  • [ 78593-33-6 ]
  • 4
  • [ 78593-33-6 ]
  • [ 115-19-5 ]
  • [ 78593-37-0 ]
  • 5
  • [ 78593-33-6 ]
  • [ 82453-25-6 ]
  • 7
  • [ 78593-33-6 ]
  • [ 78593-43-8 ]
  • 8
  • [ 335242-55-2 ]
  • [ 78593-33-6 ]
  • 9
  • [ 80334-78-7 ]
  • [ 78593-33-6 ]
  • 10
  • [ 78593-33-6 ]
  • [ 75-34-3 ]
  • [ 67-68-5 ]
  • sodium 4-(tosyloxy)benzenesulfinate [ No CAS ]
  • 3-(4-hydroxybenzenesulphonyl)cinnoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
10.2% In methanol; (a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of <strong>[78593-33-6]3-bromocinnoline</strong>, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50ml of dimethylsulphoxide was stirred and heated at -20 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield 10.2%
10.2% In methanol; (a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of <strong>[78593-33-6]3-bromocinnoline</strong>, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%
10.2% In methanol; (a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of <strong>[78593-33-6]3-bromocinnoline</strong>, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%.
10.2% In methanol; a) 3-(4-Hydroxybenzenesulphonyl)cinnoline A mixture of 2.1 g (0.01 mol) of <strong>[78593-33-6]3-bromocinnoline</strong>, 6.6 g (0.02 mol) of sodium 4-tosyloxybenzenesulphinate and 50 ml of dimethylsulphoxide was stirred and heated at 120 C. for 24 hours. The mixture was poured into water and extracted with dichloroethane. The dichloroethane solution was washed with water, dried on anhydrous sodium sulphate and filtered. The solvent was then evaporated with a rotatory evaporator to provide 2.5 g of an oily residue. The desired product was then isolated by chromatography on a silica column using dichlorethane/methanol 98/2. In this manner, 0.45 g of 3-(4-hydroxybenzenesulphonyl)cinnoline was obtained. Yield: 10.2%

  • 11
  • [ 78593-33-6 ]
  • [ 121346-70-1 ]
YieldReaction ConditionsOperation in experiment
74.6% Using the same procedure as that described above but from <strong>[78593-33-6]3-bromocinnoline</strong> there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6% M.P.: 108 C. (isopropanol)
74.6% Using the same procedure as that described above but from <strong>[78593-33-6]3-bromocinnoline</strong> there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6% M.P.: 108 C. (isopropanol)
74.6% Using the same procedure as that described above but from <strong>[78593-33-6]3-bromocinnoline</strong> there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6%. M.P.: 108 C. (isopropanol).
74.6% Using the same procedure as that described above but from <strong>[78593-33-6]3-bromocinnoline</strong> there was obtained 3-(4-methoxyphenylthio)cinnoline Yield: 74.6% M.P.: 108 C. (isopropanol)

  • 12
  • [ 78593-33-6 ]
  • [ 696-62-8 ]
  • [ 1562367-46-7 ]
  • 13
  • [ 253-66-7 ]
  • [ 78593-33-6 ]
  • 14
  • [ 78593-33-6 ]
  • [ 1357572-66-7 ]
  • C24H14BrN3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With 1-methyl-1H-imidazole; copper(l) iodide; potassium carbonate; In toluene; for 168h;Reflux; Inert atmosphere; Starting material 1-A (11.8 g, 40 mmol), starting material 1-B (16.7 g, 80 mmol), CuI (3.8 g, 20 mmol), potassium carbonate (11.1 g, 80 mmol), and 1-methyl-1H-imidazole (3.3 g, 40 mmol) were added to 250 ml of toluene, and then, the mixture was refluxed while stirring under a nitrogen atmosphere for 7 days. Then, the reaction mixture was cooled to room temperature, 300 ml of water was added to isolate the organic layer, and the water layer was extracted twice with 250 ml of dichloromethane. The extracted organic layer was stirred with MgSO4 to remove water therefrom, and the organic layer was filtered and evaporated under reduced pressure. The resulting solid was subjected to column chromatography using, as an eluent, dichloromethane and normal hexane to obtain 5.6 g of Intermediate 1-C at the yield of 33%. MS (MALDI-TOF) m/z: 424 [M]+
  • 15
  • [ 78593-33-6 ]
  • C44H26N6 [ No CAS ]
  • 16
  • [ 78593-33-6 ]
  • C44H24N6Pt [ No CAS ]
 

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Technical Information

Categories

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[ 78593-33-6 ]

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