59514-18-0|6-Bromo-2,3,4,9-tetrahydro-1H-carbazol-1-one| Ambeed

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Quality Control of [ 59514-18-0 ] Purity: 95% SDS Specification

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Product Details of [ 59514-18-0 ]

CAS No. :	59514-18-0
Formula :	C₁₂H₁₀BrNO
M.W :	264.12
SMILES Code :	O=C1C(NC2=C3C=C(Br)C=C2)=C3CCC1
MDL No. :	MFCD00459403
InChI Key :	UZMYPCOHBHVFJE-UHFFFAOYSA-N
Pubchem ID :	708529

Safety of [ 59514-18-0 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P301+P312+P330-P270-P264-P501

Computational Chemistry of [ 59514-18-0 ] Show Less

Physicochemical Properties

Num. heavy atoms	15
Num. arom. heavy atoms	9
Fraction Csp3	0.25
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	63.85
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	32.86 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.24
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	3.17
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.45
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.	2.43
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	4.25
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.11

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.92
Solubility	0.0319 mg/ml ; 0.000121 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.	-3.53
Solubility	0.0778 mg/ml ; 0.000295 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	-5.13
Solubility	0.00194 mg/ml ; 0.00000733 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	Yes
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.	-5.66 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<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)	2.02

Application In Synthesis of [ 59514-18-0 ]

* 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 [ 59514-18-0 ]

[ 59514-18-0 ] Synthesis Path-Downstream 1~35

1
[ 3456-99-3 ]
[ 59514-18-0 ]

References: [1]Journal of the Chemical Society,1934,p. 272,275.
[2]Journal of the Chemical Society,1944,p. 624.

2
[ 59514-18-0 ]
[ 75-36-5 ]
[ 876472-33-2 ]

References: [1]Journal of the Chemical Society,1934,p. 272,275.

3
[ 108606-59-3 ]
[ 59514-18-0 ]

References: [1]Journal of the Chemical Society,1934,p. 272,275.

4
[ 4774-33-8 ]
[ 59514-18-0 ]
[ 124253-94-7 ]

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1947 - 1951.
[2]Chemical and pharmaceutical bulletin,1989,vol. 37,p. 1500 - 1503.

5
[ 59514-18-0 ]
[ 64-04-0 ]
[ 132214-13-2 ]

References: [1]Pharmaceutical Chemistry Journal,1990,vol. 24,p. 826 - 829.
Khimiko-Farmatsevticheskii Zhurnal,1990,vol. 24,p. 46 - 48.

6
[ 59514-18-0 ]
6-bromo-2,3,4,9-tetrahydro-carbazol-1-one oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; hydroxylamine hydrochloride; In ethanol; for 1h;Heating / reflux;	Compound 41 is prepared from Compound 1 as follows. Pyridine (5.64 ml, 39.8 mmol) is added to a mixture of Compound 1 (5.25g, 19.9 mmol) and hydroxylamine HCl salt (2.76g, 39.8 mmol) in ethanol (EtOH). The mixture is refluxed for about 1 h, and the solids are dissolved upon heating. The reaction mixture is then concentrated to dryness. The resulting sticky solid is treated and washed with hexanes (3x) to give a tan colored power of Compound 41, 6.1g, 100%

References: [1]Patent: WO2006/58088,2006,A2 .Location in patent: Page/Page column 54.
[2]Zeitschrift fur Naturforschung, B: Chemical Sciences,1994,vol. 49,p. 687 - 690.

7
[ 108606-59-3 ]
[ 59514-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; In water; for 3h;Heating / reflux;	Example 2; Preparation of 6-bromo-N-cyclohexyl-2, 3,4, 9-tetrahydro-lH-carbazol-1-amine; a) 6-bromo-2,3, 4, 9-tetrahydro-1H-carbazol-1-one; [0105] To a round bottom flask was added 4-bromoaniline and concentrated aqueous HCl (5.8 eq). Once the mixture was cooled to 0C using an ice bath, a solution of sodium nitrite (1 eq) in water was slowly added over 30 min. The reaction was then maintained at 0C for 1 hour. A mixture of 2- (hydroxymethylene) cyclohexan-l-one (1. 5eq), sodium acetate (2.3 eq), methanol, and water was added to the above diazotized solution over 10 minutes. After stirring at 0C for 1 hour, the pure product was filtered from the reaction and washed with water. Vacuum suction was maintained overnight to yield the crude intermediate that was then mixed with concentrated aqueous HCl (5.8 eq) in glacial acetic acid and heated to reflux for 3 hours. The resulting mixture was allowed to cool to room temperature. The reaction was diluted with water (3 times the reaction volume) and the resulting slurry was extracted with ethyl acetate (4x). The organic layers were combined and dried over sodium sulfate. The resulting filtrate solution was concentrated ifz vacuo to yield the crude product, which was purified via flash chromatography using hexanes/ethyl acetate. The pure fractions were combined and concentrated ii ? vacito to yield 6-bromo-2,3, 4, 9-tetrahydro-lH-carbazol-l-one as a solid (LC/MS MH+ 264.0, Rt 2.81 min).

References: [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1947 - 1951.
[2]Patent: WO2005/37791,2005,A1 .Location in patent: Page/Page column 31-32.

8
[ 59514-18-0 ]
[ 1188-33-6 ]
6-Bromo-2-[(E)-isopropylimino]-2,3,4,9-tetrahydro-carbazol-1-one [ No CAS ]

References: [1]Pharmaceutical Chemistry Journal,1994,vol. 28,p. 566 - 569.
Khimiko-Farmatsevticheskii Zhurnal,1994,vol. 28,p. 28 - 31.

9
[ 59514-18-0 ]
[ 100-63-0 ]
3-bromo-11,12-dihydroindolo[2,3-a]carbazole [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 1239 - 1251.

10
[ 59514-18-0 ]
[ 1073-69-4 ]
3-bromo-8-chloro-11,12-dihydroindolo[2,3-a]carbazole [ No CAS ]

References: [1]Synthetic Communications,1998,vol. 28,p. 1239 - 1251.

11
[ 59514-18-0 ]
[ 68-12-2 ]
6-Bromo-1-chloro-9H-carbazole-2-carbaldehyde [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1998,vol. 37,p. 314 - 317.

12
[ 59514-18-0 ]
[ 100-63-0 ]
3-bromo-5,6,11,12-tetrahydro-11,12-diaza-indeno[2,1-a]fluorene [ No CAS ]

References: [1]Il Farmaco,2001,vol. 56,p. 229 - 232.

13
[ 765-87-7 ]
[ 589-21-9 ]
[ 59514-18-0 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; acetic acid; In methanol; at 60℃;Inert atmosphere;	To a solution of 1,2-cyclohexanedione (2243?mg, 20?mmol) and concentrated hydrochloric acid (13?mL) in acetic acid (40?mL), p-tolylhydrazine hydrochloride (1586?mg, 10?mmol) in methanol (25?mL) was added dropwise slowly over 10?min. After the addition, the resulting mixture was heated to 60?C, and stirred overnight. The solvent was evaporated, and the residue was pH adjusted to weak alkaline with saturated NaHCO3. The mixture was extracted with AcOEt (3?*?20?mL). The combined organic extract was washed with brine, dried over anhydrous Na2SO4, and concentrated. The residue was purified by silica gel chromatography (petroleum ether/AcOEt, 12/1 v/v) to give intermediate 7 (1235?mg, 62%) as a brown powder. The mixture of intermediate 7 (102?mg, 0.5?mmol), 4-phenylbutylamine (0.12?mL, 0.8?mmol) and catalytic p-TsOH in toluene (10?mL) was refluxed at 140?C for 16?h with a Dean-Stark trap in place. The solvent was evaporated and the residue was dissolved in methanol. NaBH4 (177?mg) was then added at 0?C. The solution was heated to 80?C until TLC indicated the reaction was complete. The reaction was quenched with water and concentrated. Subsequently, the mixture was extracted with AcOEt twice and the combined organic layers were dried over anhydrous Na2SO4. After evaporation of the solvent, the resulting residue was purified by column chromatography on silica gel (petroleum ether/AcOEt, 4/1 v/v) to give compound 5 (123?mg, Yield: 72%).
		General procedure: A mixture of a substituted phenylhydrazine i (3.0 mmol), 1,2-cyclohexanedione ii (6.0 mmol), and water (50 mL) was stirred at room temperature (23 C) in a 250 mL round bottom flask. After 16 h,10 mL of aqueous 1 M HCl was added and the reaction was heated to reflux. After 12 h, the reaction was refrigerated to induce crystallization. The resulting solid was filtered and air dried to provide the crude product. The desired product was purified by flash column chromatography (SiO2) using 20-30% ethyl acetate in hexanes as the eluent. NMR of products were compared to literature values to confirm structure.

References: [1]Chemical Communications,2003,p. 1822 - 1823.
[2]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 7516 - 7520.
[3]European Journal of Medicinal Chemistry,2019,vol. 162,p. 203 - 211.
[4]Bioorganic and Medicinal Chemistry Letters,2019,vol. 29,p. 1836 - 1841.

14
[ 59514-18-0 ]
[ 108-24-7 ]
[ 876472-33-2 ]