10406-06-1|5-Bromo-1H-indole-3-carboxylic acid| Ambeed

Structure of 10406-06-1

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Quality Control of [ 10406-06-1 ] Purity: 97% SDS Specification

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Product Details of [ 10406-06-1 ]

CAS No. :	10406-06-1
Formula :	C₉H₆BrNO₂
M.W :	240.05
SMILES Code :	C2=C(C(O)=O)C1=CC(=CC=C1[NH]2)Br
MDL No. :	MFCD05664007
InChI Key :	JVZMBSGNSAHFCY-UHFFFAOYSA-N
Pubchem ID :	7018243

Safety of [ 10406-06-1 ]

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

Computational Chemistry of [ 10406-06-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	2.0
Molar Refractivity	52.96
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	53.09 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.36
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.68
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.63
Log P_o/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.	1.8
Log P_o/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	2.54
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.2

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.46
Solubility	0.0827 mg/ml ; 0.000344 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.	-3.45
Solubility	0.0857 mg/ml ; 0.000357 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	-3.52
Solubility	0.0732 mg/ml ; 0.000305 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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.	-5.86 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.	0.56

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)	1.34

Application In Synthesis of [ 10406-06-1 ]

* 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 [ 10406-06-1 ]

[ 10406-06-1 ] Synthesis Path-Downstream 1~55

1
[ 32387-18-1 ]
[ 10406-06-1 ]

Yield	Reaction Conditions	Operation 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.

References: [1]Patent: EP2548864,2013,A1 .Location in patent: Paragraph 0169; 0170.
[2]Patent: WO2013/14102,2013,A1 .Location in patent: Page/Page column 26; 30; 31.
[3]Journal of Medicinal Chemistry,2014,vol. 57,p. 7293 - 7316.
[4]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4664 - 4668.
[5]Patent: US2012/277205,2012,A1 .Location in patent: Page/Page column 25.
[6]Patent: WO2012/146318,2012,A1 .Location in patent: Page/Page column 54.
[7]Russian Journal of General Chemistry,2017,vol. 87,p. 3006 - 3016.

2
[ 19353-92-5 ]
[ 10406-06-1 ]
[ 1252802-29-1 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4664 - 4668.

3
4-benzyloxy-3-methoxy-benzoic acid hydrazide [ No CAS ]
[ 10406-06-1 ]
[ 1252802-32-6 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4664 - 4668.

4
[ 10406-06-1 ]
[ 3291-03-0 ]
[ 1252802-30-4 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 4664 - 4668.

5
[ 10406-06-1 ]
[ 10406-05-0 ]

References: [1]Journal of the Korean Chemical Society,2011,vol. 55,p. 240 - 242.
[2]Journal of the Korean Chemical Society,2011,vol. 55,p. 317 - 322.

6
[ 10406-06-1 ]
[ 103858-54-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.

7
[ 10406-06-1 ]
[ 1354714-51-4 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.

8
[ 10406-06-1 ]
[ 1354714-52-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.

9
[ 10406-06-1 ]
[ 1354714-56-9 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: The intermediatesindole-2(3)-carbohydrazide (2) and indole-3-carboxaldehyde(4) were prepared starting from commercially available indole,as described previously. Indole-3-carboxylic acids 1were prepared from the reaction of indole with trifluoroaceticanhydride followed by hydrolysis with sodium hydroxide. Toobtain the corresponding ester, a solution of indole-3-carboxylicacid 1 (1 mmol) in absolute ethanol (20 mL) was refluxed witha catalytic amount of concentrated sulfuric acid for 20 h and theresidue was extracted with ethyl acetate (30 mL), washed with asaturated sodium bicarbonate solution (20 mL), dried, andevaporated. As shown in Scheme 1, a solution of theappropriate ester (1 mmol) and hydrazine hydrate (2 mmol)in ethanol (15 mL) was refluxed for 24 h and cooled, and thesolid that was obtained was filtered and recrystallized fromethanol to give pure indole-2(3)-carbohydrazide (2) in 85-90% yield.For preparation of indole-3-carboxaldehydes 4, withcontinuous stirring, phosphorous oxychloride (8.41 mL, 90mmol) was added to 0 C dimethylformamide (28 mL, 370mmol) for 30 min followed by addition of a solution of indole 3(85.47 mmol) in DMF (10 mL, 130 mmol) at roomtemperature until it became a yellow paste. At the end of thereaction, 30 g of crushed ice was added to the paste followed bydropwise addition of a sodium hydroxide solution (1 N solution, 100 mL) while the mixture was being stirred. Theresulting suspension was heated rapidly to 90 C, cooled atroom temperature, and refrigerated overnight. The product wasfiltered, washed with water (2 × 100 mL), and air-dried toafford the pure indole-3-carboxaldehydes 4 in 80-90% yields(Scheme 1).Finally, to the mixture of indole-2(3)-carboxylic acidhydrazide 2 (1 mmol) and indole-3-carboxaldehyde 4 (1mmol) in absolute ethanol (20 mL) was added a catalyticamount of glacial acetic acid, and the mixture was refluxed at 80C for 5 h and cooled and the solid that separated out wasfiltered and recrystallized from ethanol to afford bis(indolyl)-hydrazide-hydrazones in 75-90% yields (Scheme 1).

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.
[2]Biochemistry,2016,vol. 55,p. 3020 - 3035.

10
[ 10406-06-1 ]
[ 1354714-45-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.

11
[ 10406-06-1 ]
[ 1354714-47-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 212 - 215.

12
[ 768-94-5 ]
[ 10406-06-1 ]
[ 1378020-94-0 ]