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Chemical Structure| 34658-66-7 Chemical Structure| 34658-66-7

Structure of 34658-66-7

Chemical Structure| 34658-66-7

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Product Details of [ 34658-66-7 ]

CAS No. :34658-66-7
Formula : C13H9BrN2
M.W : 273.13
SMILES Code : BrC1=CC=C(C2=CN3C=CC=CC3=N2)C=C1
MDL No. :MFCD00218250
InChI Key :GRZUOGFRIHABDK-UHFFFAOYSA-N
Pubchem ID :623416

Safety of [ 34658-66-7 ]

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

Computational Chemistry of [ 34658-66-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 15
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 68.33
TPSA ?

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

17.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.82
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

3.59
Log Po/w (WLOGP)?

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

3.76
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.

2.93
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

3.15
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.25

Water Solubility

Log S (ESOL):?

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

-4.42
Solubility 0.0103 mg/ml ; 0.0000378 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.

-3.64
Solubility 0.0626 mg/ml ; 0.000229 mol/l
Class?

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

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

-5.45
Solubility 0.00096 mg/ml ; 0.00000352 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

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

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

No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-5.42 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)

2.14

Application In Synthesis of [ 34658-66-7 ]

* 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 [ 34658-66-7 ]

[ 34658-66-7 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 867044-28-8 ]
  • [ 34658-66-7 ]
  • [ 1027074-24-3 ]
YieldReaction ConditionsOperation in experiment
71% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 6h;Heating / reflux; Synthesis of Compound 1; 1.85 g of Intermediate 1c (3.90 mmol) and 1 g of Intermediate 1d (3.90 mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture while the mixture was stirred, and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered while being washed with water, ethanol and THF to obtain 1.73 g of Compound 1 in the form of a pale yellow powder (yield 71%). (1H NMR (400 MHz, CDCl3) 8.13-8.04 (7H), 8.01 (1H), 7.97-7.92 (4H), 7.86-7.82 (2H), 7.75 (2H), 7.71-7.58 (10H), 7.32 (2H), 7.15 (1H), 6.75 (1H)).
71% With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 6h;Heating / reflux; Synthesis of Compound 1; 1.85 g of Intermediate 1c (3.90 mmol) and 1 g of Intermediate 1d (3.90 mmol) were added to a mixed solvent of 2.7 g of an aqueous potassium carbonate solution (19.5 mmol) and THF. 225 mg of Pd(PPh3)4 (19.5 mmol) was added to the mixture while the mixture was stirred, and the mixture was refluxed for 6 hours. The mixture was cooled to room temperature, and then the obtained solid compound was filtered while being washed with water, ethanol and THF to obtain 1.73 g of Compound 1 in the form of a pale yellow powder (yield 71%). (1H NMR (400MHz, CDCl3) 8.13-8.04 (7H), 8.01 (1H), 7.97-7.92 (4H), 7.86-7.82 (2H), 7.75 (2H), 7.71-7.58 (10H), 7.32 (2H), 7.15 (1H),6.75(1H)).
  • 2
  • [ 56525-79-2 ]
  • [ 34658-66-7 ]
  • [ 607739-86-6 ]
YieldReaction ConditionsOperation in experiment
31% With 18-crown-6 ether; potassium carbonate;copper; In 1,2-dichloro-benzene; at 200℃; for 48h;Inert atmosphere; Into a reactor, 6.1 g (19 mmoles) of <strong>[56525-79-2]3,6-diphenylcarbazole</strong>, 6.3 g (23 mmoles) of Intermediate Compound (A), 0.2 g of copper powder, 1.7 g of 18-crown-6 and 2.9 g (21 mmoles) of potassium carbonate were placed and 30 ml of o-dichlorobenzene was added as the solvent. The resultant mixture was heated at 200° C. in a silicone oil bath under a nitrogen stream and the reaction was allowed to proceed for 48 hours. After the reaction was completed, the reaction mixture was filtered under suction before being cooled and the obtained filtrate was concentrated using an evaporator. To the obtained oily product, 30 ml of methanol was added. The formed solid substance was separated by filtration under a reduced pressure and a gray solid substance was obtained. The obtained solid substance was recrystallized from benzene and 3.0 g (the yield: 31percent) of white crystals were obtained. It was confirmed by 90 MHz 1H-NMR and FD-MS (the field desorption mass analysis) that the obtained crystals were the target substance (A5). The result of the measurement by FD-MS is shown in the following:FD-MS calcd. for C37H25N3=511; found: m/z=511 (M+, 100)
  • 3
  • [ 34658-66-7 ]
  • [ 802919-90-0 ]
  • 2-(4-bromophenyl)-3-(difluoro(phenylsulfonyl)methyl)imidazo-[1,2-a]pyridine [ No CAS ]
 

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