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Chemical Structure| 181765-86-6 Chemical Structure| 181765-86-6

Structure of 181765-86-6

Chemical Structure| 181765-86-6

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Product Details of [ 181765-86-6 ]

CAS No. :181765-86-6
Formula : C8H6BrIO2
M.W : 340.94
SMILES Code : COC(=O)C1=C(I)C=CC(Br)=C1
MDL No. :MFCD00144771
InChI Key :CJRHLSZJEFJDLA-UHFFFAOYSA-N
Pubchem ID :11078356

Safety of [ 181765-86-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P301+P312-P302+P352-P304+P340-P305+P351+P338

Computational Chemistry of [ 181765-86-6 ] Show Less

Physicochemical Properties

Num. heavy atoms 12
Num. arom. heavy atoms 6
Fraction Csp3 0.12
Num. rotatable bonds 2
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 58.14
TPSA ?

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

26.3 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

2.57
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

3.43
Log Po/w (WLOGP)?

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

2.84
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.

3.52
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

3.34
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.14

Water Solubility

Log S (ESOL):?

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

-4.35
Solubility 0.0151 mg/ml ; 0.0000444 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.

-3.66
Solubility 0.0741 mg/ml ; 0.000217 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

-4.24
Solubility 0.0195 mg/ml ; 0.0000573 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

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.

-5.94 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

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<0.0
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)

2.05

Application In Synthesis of [ 181765-86-6 ]

* 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 [ 181765-86-6 ]

[ 181765-86-6 ] Synthesis Path-Downstream   1~5

  • 3
  • [ 654664-63-8 ]
  • [ 181765-86-6 ]
  • methyl 5-bromo-2-(triphenylen-7-yl)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
57% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In ethanol; toluene; at 120℃; for 3h;Inert atmosphere; Methyl 5-bromo-2-iodobenzoate 3.64g (1eq, 10.67mmol) 2-Triphenylenylboronic acid 3.20g (1.1eq, 11.74mmol), Tetrakis (triphenylphosphine) palladium (0) 0.7g (0.04eq, 0.43mmol) and the reaction vessel into the vacuum dried and then filled with nitrogen gas. Toluene 46ml behind the dissolved compounds into the upper flask and the addition of Ethanol 23ml 2.0MSodium carbonate solution 23ml (3eq, 32.01mmol) and stirred sikimyeo reflux for 3 hours in 120 . After completion of the reaction and the organic layer was extracted with ethyl acetate and washing with distilled water. After the filter was dried with magnesium sulfateThe solvent is evaporated. Through a subsequent column chromatography Methyl 5-bromo-2- (triphenylen-7-yl) benzoate to give a 2.68g (yield = 57%).
  • 4
  • [ 2267-23-4 ]
  • [ 181765-86-6 ]
  • methyl 5-bromo-2-((2-nitro-4-(trifluoromethoxy)phenyl)amino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
64.1% With tris(triphenylphosphine)copper(I) bromide; caesium carbonate; In toluene; at 110℃; for 24h; A mixture of 2- nitro-4-(trifluoromethoxy)aniline (0.651 g, 2.93 mmol), methyl 5-bromo-2-iodobenzoate (1.00 g, 2.93 mmol), CS2CO3 (1.43 g, 4.40 mmol) and CuBr(PPh3)3 (0.546 g, 0.587 mmol) were suspended in toluene (15.0 mL). The resulting reaction mixture was heated to 110 C for 24 h, after which TLC analysis (10% EtOAc in Hex) showed completion. Reaction mixture was filtered through celite and the filtrate concentrated. The crude mixture was recrystallized from EtOH-H20 to afford methyl 5-bromo-2-((2-nitro-4- (trifluoromethoxy)phenyl)amino)benzoate (818 mg, 64.1 % yield) as orange crystals. NMR (400 MHz, DMSO-t 5) d 10.80 (s, 1H), 8.14 (dq, J= 2.5, 0.8 Hz, 1H), 8.06 (d, J= 2.5 Hz, 1H), 7.74 (dd, J= 8.9, 2.5 Hz, 1H), 7.71 - 7.65 (m, 2H), 7.52 (d, J= 8.9 Hz, 1H), 3.89 (s, 3H). 19F NMR (376 MHz, DMSO-t 5) d -57.50 (s, 3F). LCMS RT (Method 2) = 3.901 min, m/z 436.6 [M+H+]
  • 5
  • [ 1455-20-5 ]
  • [ 181765-86-6 ]
  • [ 292638-85-8 ]
  • C20H21BrO4S [ No CAS ]
 

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