23008-56-2|N-(4-Chlorophenyl)-2-nitroaniline| Ambeed

Structure of 23008-56-2

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Quality Control of [ 23008-56-2 ] Purity: 97% SDS Specification

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Product Details of [ 23008-56-2 ]

CAS No. :	23008-56-2
Formula :	C₁₂H₉ClN₂O₂
M.W :	248.67
SMILES Code :	O=[N+](C1=CC=CC=C1NC2=CC=C(Cl)C=C2)[O-]
MDL No. :	MFCD02683544
InChI Key :	RCLKXSIRDRWUGX-UHFFFAOYSA-N
Pubchem ID :	89958

Safety of [ 23008-56-2 ]

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

Computational Chemistry of [ 23008-56-2 ] Show Less

Physicochemical Properties

Num. heavy atoms	17
Num. arom. heavy atoms	12
Fraction Csp3	0.0
Num. rotatable bonds	3
Num. H-bond acceptors	2.0
Num. H-bond donors	1.0
Molar Refractivity	69.82
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	57.85 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.1
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	4.29
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.99
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.	3.51
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	1.14
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	3.01

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-4.41
Solubility	0.0097 mg/ml ; 0.000039 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.	-5.22
Solubility	0.00151 mg/ml ; 0.00000606 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	-4.97
Solubility	0.00268 mg/ml ; 0.0000108 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	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.	-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	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	2.0 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<2.0
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)	2.67

Application In Synthesis of [ 23008-56-2 ]

* 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 [ 23008-56-2 ]

[ 23008-56-2 ] Synthesis Path-Downstream 1~35

1
[ 119-75-5 ]
[ 23008-56-2 ]

References: [1]Proceedings of the Royal Irish Academy. Section B: Biological, geological, and chemical science,1953,vol. 55B,p. 157,160.

2
[ 23008-56-2 ]
[ 68817-71-0 ]

Yield	Reaction Conditions	Operation in experiment
93.2%	With iron; ammonium chloride; In ethanol; water; at 70℃; for 2h;	N2-(4-chloro henyl)benzene-l,2-diamineTo a mixture of EtOH (100 ml) and NH4C1 saturated solution (15 ml),<strong>[23008-56-2]N-(4-chlorophenyl)-2-nitrobenzenamine</strong> (5.0 g, 20.1 mmol) was added, followed by iron powder (4.0 g). The reaction mixture was heated at 70 °C for 2h. The solid was filtered and the filtrate was extracted by EA (100 mL x 3), dried over Na2S04. After the solvent was removed, the mixture was purified by Combi-flash (PE : EA = 5 : 1) to giveN1-(4-chlorophenyl)benzene-l,2-diamine (4.1 g, 93.2 percent) as a light yellow solid. LRMS (M + H+) m/z calcd 218.06; found 218. 1H NMR (300 MHz, CD3OD): delta 6.52-6.59 (m, 3H), 6.70-6.74 (m, 1H), 6.81-6.87 (m, 1H), 6.90-6.99 (m, 3H).
92%	With hydrogen; nickel; In N,N-dimethyl-formamide; at 60 - 70℃;	In the hydrogenation reactor,100 g of N- (4-chlorophenyl) -2-nitro-1-aniline and 200 g of DMF were charged,After nitrogen replacement,Put 10 grams of nickel metal catalyst.Turn on stirringWarming to 60 degrees,Hydrogen gas to 3 kg pressure.Continuous access to hydrogen at 60 to 70 degrees,Until it no longer absorbs hydrogen,HPLC-controlled reaction process.When the condensate intermediate disappears,The reaction reached the end.Nitrogen replacement reaction system,Nickel catalyst was removed by hot filtration.The resulting filtrate was concentrated under reduced pressure to give about 100 g of DMF,Add 200 grams of deionized water,After slowly cooling to 20 degrees crystallization.The solid was isolated by filtration,After the solid was washed with appropriate amount of deionized water,Then cold toluene washing, drying.Finally, 81 g of crude N- (4-chlorophenyl) -1,2-phenylenediamine was obtained,Yield 92percentPurity greater than 98percentColor is gray brown.
	With acetic acid; zinc; In dichloromethane;	To a solution of 2-(4-chloroanilino)- nitrobenzene (57.0 g) in CH2C12 (40 mL) was added AcOH (90 mL), then Zn (105 g) was added in small potions. After Zn was added, the color of the mixture became light green, filtered by suction, washed with CH2C12. The filtrate was concentrated to dryness. Water was added, filtered, and washed with water to give a brown solid. This solid was used directly in the next step without further purification

	With hydrogenchloride; iron; In water; at 90℃;	General procedure: To a slurry containing iron powder (94.5 mmol) and distilled water(20 mL), the crude 2-nitro-N-phenylanilinewas added at room temperature. Upon dropwise addition of concentratedhydrochloric acid (0.3 mL), the mixture was stirred at 90 C for 1-2 hours.Reaction completion was confirmed via TLC and the mixture was cooled to roomtemperature. The mixture was extracted with ether (5 x 20 mL) and the organicphase was evaporated in vacuo toobtain intermediates 4a-j.3
	With iron; acetic acid; In water; ethyl acetate; for 6h;Reflux;	General procedure: A mixture of N-substituted-2-nitroanilines (50 mmol), ironpowder (250 mmol), acetic acid (500 mmol), water (35 ml) andethyl acetate (80 ml) was heated to reflux for 6 h. After completionof the reaction as indicated by TLC, the mixture was filtered immediately.The organic layer of the filtrate was separated, washedwith water, dried over anhydrous Na2SO4 and concentrated underreduced pressure to obtain diamines (16a?16n) as a brown solid.
	With iron; ammonium chloride; In ethanol; water; at 90℃; for 3h;	General procedure: The main procedure is shown in Scheme 2. The raw products of compound 7 were synthesized via one-pot method in a flask containing compounds 5 (30 mmol), 6 (30 mmol), K2CO3 (15 mmol) and PEG1000 (0.45 mmol). The reactions were carried out under stirring at 185 °C and were monitored by TLC. After reactions completion, the desired diphenylamine derivatives 7 were obtained via column chromatographic purification. Next, compounds 7 (20 mmol), reductive iron powder (60 mmol), solid NH4Cl (60 mmol) and ethanol aqueous solution (75percent, 50 mL) were added. The reactions proceeded with refluxing for 3 h at 90 °C and compounds 8 were obtained. Then, compound 3 (30 mmol) and SOCl2 (thionylchloride, 30 mL) were added. The mixture was heated to reflux at 90 °C for 3 h. Residual SOCl2 was removed by vacuum distillation in order to obtain compound 4. Finally, the primary amines 8 (10 mmol) dissolved in dichloromethane (CH2Cl2, 5 mL) and triethylamine(Et3N, 10 mL) were added. The mixture was cooled to 0 °C and compound 4 (20 mmol) dissolved in dichloromethane (CH2Cl2, 10 mL) was added dropwise under stirring at a temperature not exceeding 5 °C. The final mixture was stirred at room temperature for 10 h and the target compounds 9a, 9b and 9c were purified via column chromatography and recrystallization.

References: [1]Chinese Journal of Chemistry,2013,vol. 31,p. 1473 - 1482.
[2]Organic Process Research and Development,2016,vol. 20,p. 452 - 464.
[3]Patent: WO2012/151512,2012,A2 .Location in patent: Page/Page column 103-104.
[4]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 145 - 150.
[5]Patent: CN107445845,2017,A .Location in patent: Paragraph 0047; 0048; 0049; 0050; 0051; 0052.
[6]Chemische Berichte,1902,vol. 35,p. 957 Anm..
[7]Liebigs Annales,1995,p. 1275 - 1282.
[8]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1923 - 1926.
[9]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3138 - 3141.
[10]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5443 - 5448.
[11]Patent: WO2012/3190,2012,A1 .Location in patent: Page/Page column 45.
[12]Molecules,2012,vol. 17,p. 4545 - 4559.
[13]Chinese Chemical Letters,2012,vol. 23,p. 707 - 710.
[14]Journal of Medicinal Chemistry,2012,vol. 55,p. 8409 - 8417,9.
[15]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 90 - 93.
[16]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 4475 - 4486.
[17]Chinese Chemical Letters,2017,vol. 28,p. 1731 - 1736.

3
[ 23008-56-2 ]
[ 99979-13-2 ]

References: [1]Journal of the Chemical Society,1958,p. 4492.

4
[ 127-09-3 ]
[ 106-47-8 ]
[ 88-73-3 ]
[ 23008-56-2 ]

References: [1]Chemische Berichte,1902,vol. 35,p. 957 Anm..

5
[ 106-47-8 ]
[ 88-73-3 ]
[ 23008-56-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: Anhydrous potassium carbonate (2.76 g, 22 mmol)was added to compound 1 (22 mmol) at120 C and the mixture was stirred for 10-20 minutes. The substituted anilines 2a-jwere added slowlyand the resulting mixtures were heated at 165 C for 2 hours. Thereaction mixtures were then quenched with hot water at 120 C, washed with 5percentsodium hydroxide solution (3 x 30 mL) at the same temperature and the orgnicphase was separated off using a separating funnel to 2-nitro-N-phenylaniline (Yields: 75 percent - 95 percent).2The products were used in the next step without further purication.
	With potassium carbonate; at 185℃;	General procedure: The main procedure is shown in Scheme 2. The raw products of compound 7 were synthesized via one-pot method in a flask containing compounds 5 (30 mmol), 6 (30 mmol), K2CO3 (15 mmol) and PEG1000 (0.45 mmol). The reactions were carried out under stirring at 185 °C and were monitored by TLC. After reactions completion, the desired diphenylamine derivatives 7 were obtained via column chromatographic purification. Next, compounds 7 (20 mmol), reductive iron powder (60 mmol), solid NH4Cl (60 mmol) and ethanol aqueous solution (75percent, 50 mL) were added. The reactions proceeded with refluxing for 3 h at 90 °C and compounds 8 were obtained. Then, compound 3 (30 mmol) and SOCl2 (thionylchloride, 30 mL) were added. The mixture was heated to reflux at 90 °C for 3 h. Residual SOCl2 was removed by vacuum distillation in order to obtain compound 4. Finally, the primary amines 8 (10 mmol) dissolved in dichloromethane (CH2Cl2, 5 mL) and triethylamine(Et3N, 10 mL) were added. The mixture was cooled to 0 °C and compound 4 (20 mmol) dissolved in dichloromethane (CH2Cl2, 10 mL) was added dropwise under stirring at a temperature not exceeding 5 °C. The final mixture was stirred at room temperature for 10 h and the target compounds 9a, 9b and 9c were purified via column chromatography and recrystallization.

References: [1]Synthetic Communications,2003,vol. 33,p. 2899 - 2906.
[2]Synlett,2003,p. 564 - 566.
[3]Zhurnal Prikladnoi Khimii,1948,vol. 21,p. 987,988.
Chem.Abstr.,1949,p. 6175.
[4]Journal of the Chemical Society,1949,p. 227,229.
[5]Chemische Berichte,1902,vol. 35,p. 957 Anm..
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 1923 - 1926.
[7]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 90 - 93.
[8]Chinese Chemical Letters,2017,vol. 28,p. 1731 - 1736.

6
[ 106-47-8 ]
[ 1493-27-2 ]
[ 23008-56-2 ]

Yield	Reaction Conditions	Operation in experiment
93.9%	With triethylamine; at 105 - 115℃; for 12h;	107.6 g of triethylamine, 150 g of o-fluoronitrobenzene,P-chloroaniline (203.4 g), the system was heated to 105-115 C for 12 hours,HPLC showed that the reaction was complete,After cooling to 20-30 C,The filter cake was washed with 150 mL of methanol,Drying, get 248g products. Purity 99.8%Yield 93.9%.
72.3%		General procedure: To the suspension of NaH (75 mol) in DMF (60 mL), substitutedamines (50 mmol) was added at 0 C. The mixture was stirred for30 min at the same temperature, and then 2-fluoronitrobenzene(60 mmol) diluted in DMF (30 mL) was added slowly. The mixturewas warmed to room temperature and stirred for 16 h. The reactionmixture was carefully poured into stirring saturated NH4Cl(500 mL), then filtered. The filter cake was washed with water,and recrystallized from methanol to afford corresponding N-aryl-2-nitroanilines 15a-15n.6.2.8 N-(4-chlorophenyl)-2-nitroaniline (15h) Orange solid; Yield: 72.3%; M.p.: 135.1-137.0 C; 1H NMR (400 MHz, DMSO-d6) delta 9.31 (s, 1H), 8.12 (d, J = 8.0, 1H), 7.53(t, J = 7.6 Hz, 1H), 7.44 (d, J = 8.8 Hz, 2H), 7.34 (d, J = 8.8 Hz, 2H), 7.22 (d, J = 8.4 Hz, 1H), 6.93 (t, J = 7.6 Hz, 1H); MS (ESI) m/z (%): 247.2 [M-H]-.
72%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl acetamide; at 120 - 125℃; for 8h;Inert atmosphere;	In the reaction flask,Put 87 g of o-fluoronitrobenzeneAnd 200 grams of DMAC,94 grams of diisopropylethylamine was added with stirring,After warming to 120 degrees under nitrogen.71 grams of p-chloroaniline was dissolved in 100 grams of DMAC to prepare a solution,After that, the solution was slowly added dropwise to the above reaction system.Dropping temperature will rise during the process,The reaction temperature should be controlled by cooling within 125 degrees.The reaction was continued at 120 to 125 degrees for 8 hours,HPLC monitors the progress of the reaction.When the content of chloroaniline is not declining,At the end of the reaction, about 11% of the chloroaniline remained.Cool to 60 degrees.After the same way with the first embodiment,Finally, 100 g of the condensate intermediate N- (4-chlorophenyl) -2-nitro-1-aniline,Yield 72%HPLC purity> 98%.

52%	With potassium fluoride; potassium carbonate; In dichloromethane; at 220℃; for 0.466667h;Microwave irradiation;	N-(4-chlorophenyl)-2-nitrobenzenamineA mixture of 2-fluoronitrobenzene (3.5 g, 24.8 mmol), 4-chlorobenzenamine (3.05 g, 24.0 mmol), K2C03 (3.45 g, 25.0 mmol) and KF (1.5 g, 25.8 mmol) was heated at 220 C for 28 min under microwave condition. The solid was dissolved in DCM (150 mL), washed with water (50 mL x 3), dried over Na2S04. The solvent was evaporated in vacuo, and then the mixture was purified by Combi-flash (PE : EA = 20 : 1) to give N-(4-chlorophenyl)-2-nitrobenzenamine (3.2 g, 52%) as a scarlet solid. 1H NMR (300 MHz, CD3OD): delta 6.82-6.87 (m, 1H), 7.27-7.31 (m, 2H), 7.41-7.45 (m, 3H), 7.70-7.73 (m, 1H), 8.15-8.18 (m, 1H).
	In pyridine; water;	Referential Example 16 2-(4-Chlorophenylamino)nitrobenzene 2-Fluoronitrobenzene (3.0 g) and 4-chloroaniline (2.5 g) were dissolved in pyridine (30 ml) and stirred at 80 C. for 18 hours. The resultant solution was allowed to cool, and thereafter, water (100 ml) was added thereto and the mixture was extracted with ethyl acetate (50 ml*3). The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was re-crystallized from ethyl acetate-hexane, to thereby yield the target compound (2.5 g) as pale-brown crystals. 1H-NMR(270 MHz, CDCl3) delta: 9.40 (1H, brs), 8.20 (1H, dd, J=8.58 Hz), 7.37 (2H, d, J=8.90 Hz), 7.35~7.39 (2H, m), 7.21 (2H, d, J=8.90 Hz), 7.15~7.19 (2H, m), 6.80 (1H, t, J=7.26 Hz).
	With potassium fluoride; at 180℃; for 10h;	A mixture of 2-fluoro-nitrobenzene (33.7 g), 4-chloroanilinc (61.0 g) and anhydrous potassium fluoride (13.9 g) was stirred at 180 C for 10 h. After being cooled to rt, 3 M HC1 was added and the mixture was stirred at 100 C for 30 min. Then cooled to rt, filtered by suction, washed with water to give a brown solid. The solid was dissolved in CH2CI2 and filtered through a thin pad of silica gel, washed with CH2CI2. The filtrate was concentrated to dryness, and the residue was recrystallized with 95% ethanol to give 57.0 g of orange solid.

References: [1]Patent: CN106916069,2017,A .Location in patent: Paragraph 0016; 0017; 0018; 0019; 0020; 0021; 0022-0024.
[2]Organic Process Research and Development,2016,vol. 20,p. 452 - 464.
[3]Molecules,2012,vol. 17,p. 4545 - 4559.
[4]Synlett,2003,p. 564 - 566.
[5]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 4475 - 4486.
[6]Patent: CN107445845,2017,A .Location in patent: Paragraph 0033; 0034; 0035; 0036; 0037; 0038; 0039-0045.
[7]Synthesis,1980,p. 215.
[8]Chinese Journal of Chemistry,2013,vol. 31,p. 1473 - 1482.
[9]Patent: WO2012/151512,2012,A2 .Location in patent: Page/Page column 103.
[10]ACS Medicinal Chemistry Letters,2016,vol. 7,p. 145 - 150.
[11]Liebigs Annales,1995,p. 1275 - 1282.
[12]Patent: US6403607,2002,B1 .
[13]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 3138 - 3141.
[14]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5443 - 5448.
[15]Patent: WO2012/3190,2012,A1 .Location in patent: Page/Page column 44-45.
[16]Chinese Chemical Letters,2012,vol. 23,p. 707 - 710.
[17]Journal of Medicinal Chemistry,2012,vol. 55,p. 8409 - 8417,9.
[18]European Journal of Organic Chemistry,2019,vol. 2019,p. 5161 - 5164.

9
[ 23008-56-2 ]
2-[3-(4-{2-[10-(4-chloro-phenyl)-3-(4-chloro-phenylamino)-10H-phenazin-2-ylideneamino]-ethyl}-piperazin-1-yl)-propyl]-isoindole-1,3-dione [ No CAS ]