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Structure of 1203578-65-7

Chemical Structure| 1203578-65-7

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Product Details of [ 1203578-65-7 ]

CAS No. :1203578-65-7
Formula : C15H10BrN
M.W : 284.15
SMILES Code : BrC1=CC=C2C=CC(C3=CC=CC=C3)=NC2=C1
MDL No. :MFCD14702481
InChI Key :QRUXWUPPMOLJKM-UHFFFAOYSA-N
Pubchem ID :17918062

Safety of [ 1203578-65-7 ]

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

Computational Chemistry of [ 1203578-65-7 ] Show Less

Physicochemical Properties

Num. heavy atoms 17
Num. arom. heavy atoms 16
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 1.0
Num. H-bond donors 0.0
Molar Refractivity 74.88
TPSA ?

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

12.89 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.9
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

4.59
Log Po/w (WLOGP)?

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

4.66
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.

3.92
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

4.7
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

4.15

Water Solubility

Log S (ESOL):?

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

-5.12
Solubility 0.00214 mg/ml ; 0.00000752 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.

-4.58
Solubility 0.00739 mg/ml ; 0.000026 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

-7.07
Solubility 0.0000245 mg/ml ; 0.0000000861 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

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.

-4.77 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<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)

1.99

Application In Synthesis of [ 1203578-65-7 ]

* 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.

  • Upstream synthesis route of [ 1203578-65-7 ]

[ 1203578-65-7 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 946122-05-0 ]
  • [ 98-86-2 ]
  • [ 1203578-65-7 ]
YieldReaction ConditionsOperation in experiment
94% With [(η5-C5Me5)Ir(6,6'-dihydroxy-2,2'-bipyridine)(H2O)]OTf2; potassium hydroxide In water for 12 h; Reflux; Green chemistry Acetophenone (144 mg, 1.2 mmol),[Cp * Ir (6,6 '- (OH) 2bpy) (H2O)] [OTf] 2 (8.3mg, 0.01mmol, 1molpercent), potassium hydroxide (56mg, 1.0mmol, 1.0 equiv.),2-Amino-4-bromobenzyl alcohol (201 mg, 1.0 mmol) and water (1 mL) were sequentially added to a 5 mL round bottom flask. After the reaction mixture was refluxed in air for 12 hours,Cool to room temperature. It was extracted with ethyl acetate, the solvent was removed by rotary evaporation and then purified by column chromatography (developing solvent: petroleum ether / acetic acidEthyl ester) to give the pure target compound in a yield of 94percent
References: [1] Patent: CN107400084, 2017, A, . Location in patent: Paragraph 0141; 0142; 0143.
[2] Organic Letters, 2016, vol. 18, # 15, p. 3558 - 3561.
[3] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 274 - 284.
  • 2
  • [ 98-80-6 ]
  • [ 1203578-65-7 ]
YieldReaction ConditionsOperation in experiment
60% With sodium persulfate; silver nitrate; trifluoroacetic acid In dichloromethane; water at 25℃; for 0.5 h; General procedure: A dried glass reaction tube equipped with a magnetic stir bar was charged with 1a (1.5 mmol, 3.0 equiv), Na2S2O8 (0.5 mmol, 1.0 equiv) and AgNO3 (0.15 mmol, 0.3 equiv), 2a (0.5 mmol, 1.0 equiv), DCM:H2O = 1:1 (4.0 mL). The resulting mixture was then stirred at 25°C for 0.5 h. The crude production was diluted with EA and Na2CO3 aqueous solution (1 mol/L) and then the resulting mixture was filtered through a pad of Celite. The filtrate was extracted with Na2CO3 aqueous solution (1 mol/L, 20 mL), and the aqueous layer was extracted with EA (3 × 10 mL). The combined organic layers dried over anhydrous Na2SO4, concentrated in vacuo, and purified by flash column chromatograph to give the pure products. The products were characterized by 1H NMR, 13C NMR, LC-MS.
References: [1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1065 - 1068.
  • 3
  • [ 946122-05-0 ]
  • [ 98-85-1 ]
  • [ 1203578-65-7 ]
References: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 274 - 284.
  • 4
  • [ 5551-12-2 ]
  • [ 1636-34-6 ]
  • [ 1203578-65-7 ]
References: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 11, p. 2216 - 2220.
  • 5
  • [ 67-68-5 ]
  • [ 98-86-2 ]
  • [ 591-19-5 ]
  • [ 1203578-65-7 ]
References: [1] Advanced Synthesis and Catalysis, 2018, vol. 360, # 14, p. 2691 - 2695.
  • 6
  • [ 59278-65-8 ]
  • [ 98-86-2 ]
  • [ 1203578-65-7 ]
References: [1] Synthesis, 2010, # 10, p. 1678 - 1686.
  • 7
  • [ 115976-33-5 ]
  • [ 1203578-65-7 ]
References: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 274 - 284.
  • 8
  • [ 98-85-1 ]
  • [ 1203578-65-7 ]
References: [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 2, p. 274 - 284.
  • 9
  • [ 5551-12-2 ]
  • [ 1203578-65-7 ]
References: [1] Journal of Organic Chemistry, 2018, vol. 83, # 9, p. 5177 - 5186.
  • 10
  • [ 98-86-2 ]
  • [ 1203578-65-7 ]
References: [1] Journal of Organic Chemistry, 2018, vol. 83, # 9, p. 5177 - 5186.
  • 11
  • [ 5551-12-2 ]
  • [ 98-86-2 ]
  • [ 1203578-65-7 ]
References: [1] Antimicrobial Agents and Chemotherapy, 2018, vol. 62, # 2, .
  • 12
  • [ 860720-24-7 ]
  • [ 1203578-65-7 ]
References: [1] Tetrahedron Letters, 2018, vol. 59, # 11, p. 1065 - 1068.
 

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