Home Cart Sign in  
Chemical Structure| 32387-18-1 Chemical Structure| 32387-18-1

Structure of 32387-18-1

Chemical Structure| 32387-18-1

*Storage: {[sel_prStorage]}

*Shipping: {[sel_prShipping]}

,{[proInfo.pro_purity]}

4.5 *For Research Use Only !

{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]} Purity: {[proInfo.pro_purity]}

Change View

Size Price VIP Price

US Stock

Global Stock

In Stock
{[ item.pr_size ]} Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

  • {[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

  • 1-2 Day Shipping
  • High Quality
  • Technical Support
Product Citations

Alternative Products

Product Details of [ 32387-18-1 ]

CAS No. :32387-18-1
Formula : C10H5BrF3NO
M.W : 292.05
SMILES Code : O=C(C1=CNC2=C1C=C(Br)C=C2)C(F)(F)F
MDL No. :MFCD03721051
InChI Key :DOBUKNJLDXQMFC-UHFFFAOYSA-N
Pubchem ID :2187699

Safety of [ 32387-18-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H320-H335
Precautionary Statements:P264-P270-P301+P312-P330

Computational Chemistry of [ 32387-18-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 16
Num. arom. heavy atoms 9
Fraction Csp3 0.1
Num. rotatable bonds 2
Num. H-bond acceptors 4.0
Num. H-bond donors 1.0
Molar Refractivity 56.38
TPSA ?

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

32.86 Ų

Lipophilicity

Log Po/w (iLOGP)?

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

1.85
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

3.54
Log Po/w (WLOGP)?

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

4.94
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.

2.29
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

4.04
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

3.33

Water Solubility

Log S (ESOL):?

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

-4.17
Solubility 0.02 mg/ml ; 0.0000684 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.

-3.91
Solubility 0.0355 mg/ml ; 0.000122 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

-4.96
Solubility 0.00318 mg/ml ; 0.0000109 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

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.

-5.57 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)

1.54

Application In Synthesis of [ 32387-18-1 ]

* 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 [ 32387-18-1 ]

[ 32387-18-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 32387-18-1 ]
  • [ 10406-06-1 ]
YieldReaction ConditionsOperation in experiment
100% A flask was charged with 1-(5-bromo-1H-indol-3-yl)-2,2,2-trifluoroethanone (hb) (4.30 g, 14.72 mmol) and an aqueous solution of sodium hydroxide (180 mL, 20% wt.) was added. This mixture was refluxed for 2h30 then carefully acidified to pH = 1 with an aqueous solution of 6M HCl. During this acidification, the carboxylic acid precipitated. The resulting suspension was filtered. The solid was washed with water and dissolved in a mixture of ethyl acetate/methanol (about 9/1). The organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. The desired product (2b) (3.528 g, 14.7 mmol) was obtained as a beige solid. Yield: quant. 1H NMR (300 MHz, DMSO-d6): delta = 7.30 (dd, J = 2.1 and 8.7 Hz, 1H, CH), 7.45 (d, J = 8.7 Hz, 1H, CH), 8.04 (d, J = 3.0 Hz, 1H, CH), 8.12 (d, J = 2.1 Hz, 1H, CH), 12.09 (br s, 1H, NH) ppm. 13C NMR (75.5 MHz, DMSO-d6): delta = 107.0 (C), 113.8 (CH), 114.4 (C), 122.6 (CH), 124.6 (CH), 127.8 (C), 133.4 (CH), 135.2 (C), 165.6 (CO) ppm.
100% A flask was charged with 1-(5-bromo-lH-indol-3-yl)-2,2,2-trifluoroethanone (hb) (4.30 g, 14.72 mmol) and an aqueous solution of sodium hydroxide (180 mL, 20% wt.) was added. This mixture was refluxed for 2h30 then carefully acidified to pH = 1 with an aqueous solution of 6M HCl. During this acidification, the carboxylic acid precipitated. The resulting suspension was filtered. The solid was washed with water and dissolved in a mixture of ethyl acetate/methanol (about 9/1). The organic layer was dried over anhydrous MgSO4 and evaporated under vacuum. The desired product (2b) (3.528 g, 14.7 mmol) was obtained as a beige solid. Yield: quant.1H NMR (300 MHz, DMSO-d6): delta = 7.30 (dd, J = 2.1 and 8.7 Hz, 1H, CH), 7.45 (d, J = 8.7 Hz, 1H, CH), 8.04 (d, J = 3.0 Hz, 1H, CH), 8.12 (d, J = 2.1 Hz, 1H, CH), 12.09 (br s, 1H, NH) ppm. 13C NMR (75.5 MHz, DMSO-d6): delta = 107.0 (C), 113.8 (CH), 114.4 (C), 122.6 (CH), 124.6 (CH), 127.8 (C), 133.4 (CH), 135.2 (C), 165.6 (CO) ppm.
24 g of the compound obtained in Preparation 1.1 is added to a solution of 46.1 g of potassium hydroxide in 25 ml of water, and is heated for 4 hours under reflux. The reaction mixture is cooled and is washed with ether, The aqueous phase is cooled to 5 C. and is then neutralized with a solution of phosphate buffer preloaded with 35% hydrochloric acid. The precipitate formed is drained and is washed with water. 15.6 g of the expected compound is obtained in the form of a white powder,m.p.=234 C.1H NMR: DMSO-d6 (250 MHz): delta (ppm): 7.32 (1H, d); 7.46 (1H, d); 8.06 (1H, s); 8.14 (1H, s); 12.00/7H, br).
2. Preparations of the compounds of formula (VIII: X = CH).Preparation 2.15-Bromo-1 /-/-indole-3-carboxylic acid(VIII): X = CH; R4 = Br; R5 = H.24 g of the compound obtained in Preparation 1 .1 is added to a solution of 46.1 g of potassium hydroxide in 25 ml of water, and is heated for 4 hours under reflux. The reaction mixture is cooled and is washed with ether. The aqueous phase is cooled to 5C and is then neutralized with a solution of phosphate buffer preloaded with 35% hydrochloric acid. The precipitate formed is drained and is washed with water. 15.6 g of the expected compound is obtained in the form of a white powder.m.p. = 234C.1H NMR: DMSO-de (250 MHz): delta (ppm): 7.32 (1 H, d); 7.46 (1 H, d); 8.06 (1 H, s); 8.14 (1 H, s); 12.00 (2H, br).
With sodium hydroxide; at 55℃; General procedure: One of compounds 3a-3f (20 mmol) was dissolved in DMF (10 mL). Trifluoroacetic anhydride (4.2 mL, 30 mmol) was added dropwise at 0C. After stirring for 3.5 h, water was added, the solid filtered off and treated with 20% NaOH (40 mL, 0.2 mol) at 55C overnight. Upon cooling down, the solution was extracted with Et2O. The aqueous phase was acidified with concentrated HCl and the residue was filtered off to give one of compounds 4a-4f.

 

Historical Records

Technical Information

Categories