[ CAS No. 144511-13-7 ] {[proInfo.proName]}

Name: 144511-13-7|6,9-Difluorobenzo[g]isoquinoline-5,10-dione|97%
Brand: Ambeed
SKU: A145788
Price: 7.0 USD
Availability: InStock
Rating: 93 (28 reviews)

,{[proInfo.pro_purity]}

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

DV 2D 3D

3d Animation Molecule Structure of 144511-13-7

Structure of 144511-13-7 * Storage: {[proInfo.prStorage]}

Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Search after Editing

* Storage: {[proInfo.prStorage]}

For Research Only 110K+ Compounds Competitive Price 1-2 Day Shipping

Quality Control of [ 144511-13-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 144511-13-7 ]

SDS Specification

Alternatived Products of [ 144511-13-7 ]

Product Details of [ 144511-13-7 ]

CAS No. :	144511-13-7	MDL No. :	MFCD16556221
Formula :	C₁₃H₅F₂NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	SCOHHAVQFVXLPO-UHFFFAOYSA-N
M.W :	245.18	Pubchem ID :	10105904
Synonyms :

Calculated chemistry of [ 144511-13-7 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	5.0
Num. H-bond donors :	0.0
Molar Refractivity :	57.46
TPSA :	47.03 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.38 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.28
Log Po/w (XLOGP3) :	2.0
Log Po/w (WLOGP) :	2.98
Log Po/w (MLOGP) :	1.52
Log Po/w (SILICOS-IT) :	3.8
Consensus Log Po/w :	2.32

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.11
Solubility :	0.189 mg/ml ; 0.00077 mol/l
Class :	Soluble
Log S (Ali) :	-2.61
Solubility :	0.596 mg/ml ; 0.00243 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.43
Solubility :	0.000901 mg/ml ; 0.00000367 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.22

Safety of [ 144511-13-7 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 144511-13-7 ]

* 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.

Upstream synthesis route of [ 144511-13-7 ]
Downstream synthetic route of [ 144511-13-7 ]

[ 144511-13-7 ] Synthesis Path-Upstream 1~6

1
[ 144511-12-6 ]
[ 144511-11-5 ]
[ 144511-13-7 ]

Reference： [1] Patent: EP503537, 1992, A1,
[2] Patent: US5506232, 1996, A,

2
[ 4664-08-8 ]
[ 540-36-3 ]
[ 144511-13-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 828 - 837
[2] Journal of Medicinal Chemistry, 2010, vol. 53, # 19, p. 6851 - 6866
[3] Patent: CN104557704, 2017, B, . Location in patent: Paragraph 0045; 0046; 0047; 0048; 0049; 0050; 0051

3
[ 188622-59-5 ]
[ 144511-13-7 ]

Reference： [1] Journal of Heterocyclic Chemistry, 1997, vol. 34, # 1, p. 27 - 32

4
[ 490-11-9 ]
[ 144511-13-7 ]

Reference： [1] Journal of Medicinal Chemistry, 1994, vol. 37, # 6, p. 828 - 837
[2] Patent: CN104557704, 2017, B,

5
[ 626-60-8 ]
[ 111608-80-1 ]
[ 144511-13-7 ]

Reference： [1] Journal of Fluorine Chemistry, 1994, vol. 68, # 2, p. 131 - 134

6
[ 144511-11-5 ]
[ 144511-13-7 ]

Reference： [1] Patent: US2005/222190, 2005, A1, . Location in patent: Page/Page column 5

[ 144511-13-7 ] Synthesis Path-Downstream 1~88

1
[ 7154-73-6 ]
[ 144511-13-7 ]
6,9-bis<(2-pyrrolidinoethyl)amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

2
[ 2038-03-1 ]
[ 144511-13-7 ]
6,9-bis<(2-morpholinoethyl)amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

3
[ 110-72-5 ]
[ 144511-13-7 ]
6,9-bis<<2-(ethylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In pyridine; methanol; chloroform;	Example 23 6,9-bis[2-(ethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione (10n) A solution of N-ethylethylenediamine (400 mg, 4.5 mmol) in pyridine (1 ml) was added to compound 9 (98 mg, 0.40 mmol) in pyridine (1 ml). The mixture was stirred at room temperature for 66 h. The pyridine and excess diamine were removed under a slow nitrogen stream and the residual material was placed under vacuum overnight. Chloroform was then added and the chloroform washed twice with cold water. The chloroform extract was dried over MgSO4 and the solvent removed by rotary evaporation. The resultant blue solid was purified by column chromatography over silica gel using 5% methanol/95% chloroform as the initial eluant. The eluant was gradually changed to 5%, 10% and then 50% methanol in chloroform. The desired product was eluted using 50% methanol/48% chloroform/2% ammonium hydroxide. Removal of the solvent led to 32 mg (21%) of product (10n). mp 101-102C. 1H NMR (CDCl3) 11.10 (m, 1H), 11.00 (m, 1H), 9.6 (s, 1H), 8.9 (d, 1H), 8.05 (d, 1H), 7.3 (m, 2H), 3.55 (m, 4H), 3.0 (t, 4H), 2.8 (q, 4H), 1.15 (t, 6H).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

4
[ 4664-08-8 ]
[ 540-36-3 ]
[ 144511-13-7 ]

Yield	Reaction Conditions	Operation in experiment
		Take a dry lumpPyridine dicarboxylic acidanhydride90gCrushed with a mortarAnd powdered aluminum trichloride 370g Stir mixing,Divided equally into 6 equal parts,Sub-bag packaging,Store in desiccator.In a 2 L round bottomed flask equipped with a drying tube,Add difluorobenzene 600mL,Outer bath 110 ,Mechanical stirring were added to the above 6 equal parts of solid powder,Add an average of 20min every minute,After adding continue to return 1h.Then concentrated under reduced pressure,Recovery of difluorobenzene, residual residue,Slowly add hydrochloric acid solution 1.5L (containing concentrated hydrochloric acid 160mL)After completion of the dropwise addition and stirring overnight, filtered, The filter cake was washed with water (200 mL)The filter cake was stirred in a mixture of ethyl acetate: petroleum ether = 1: 1 (500 mL) for 3 h,The filter cake was washed with ethyl acetate: petroleum ether = 1: 1 (100 mL) and dried in vacuo at 45 C.In a 1L round bottomed flask equipped with a drying tube,Fuco acylated product (120 g, 0.456 mol)And fuming sulfuric acid 300mL,Outside the bath 140 , reflux 3h.Cool to 60 ,To the water 6L was added NaOH350g.The cooled reaction liquid was added dropwise to an aqueous alkali solution and adjusted to pH = 5 with a NaOH solution,Then sulfuric acid pH = 1,0 ~ 5 low temperature stirring 2h.filter,The solid was dissolved in a mixture of dichloromethane (2 L + 1 L)Stir the liquid separation, emulsification,Filter demulsification.The aqueous layer was extracted with dichloromethane 1 L,Combine several layers and rinse (100 mL * 3).The organic layer was dried over Na 2 SO 4,Filtration, sodium sulfate will absorb a small amount of purple material,Concentrate the methylene chloride,Beige yellow solid.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Journal of Medicinal Chemistry,2010,vol. 53,p. 6851 - 6866
[3]Patent: CN104557704,2017,B .Location in patent: Paragraph 0045; 0046; 0047; 0048; 0049; 0050; 0051

5
[ 111-39-7 ]
[ 144511-13-7 ]
6,9-bis<<2-(propylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform;	Example 24 6,9-bis[2-(propylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione (10o) A solution of N-propylethylenediamine (403 mg, 4.0 mmol) in pyridine (1 ml) was added to compound 9 (98 mg, 0.40 mmol) in pyridine (1 ml). The reaction mixture was stirred at room temperature for 24 h and concentrated under a slow stream of nitrogen. The residual materaial was placed under vacuum overnight. Ice water was added to the residual and the aqueous layer was extracted with chloroform (5 x 40 ml). The extracts were dried over magnesium sulfate and the chloroform removed by rotary evaporation. The blue solid was purified by column chromatography over silica gel. The initial eluant was 5% methanol/95% chloroform followed by increasing the methanol amounts gradually to 10%, 20%, 30%, 40% and 50%. The desired compound coluld be eluted using 60% methanol/40% chloroform containing some ammonium hydroxide. Removal of the eluant led to 50 mg (30%) of the product (10o). mp 105-106C. 1H NMR (CDCl3) 11.15 (m, 1H), 11.05 (m, 1H), 9.6 (s, 1H), 8.9 (d, 1H), 8.10 (d, 1H), 7.3 (m, 2H), 3.6 (m, m, 4H), 3.0 (t, 4H), 2.75 (t, 4H), 1.6 (m, 4H, H2O peak superimposed), 0.95 (t, 6H).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

6
[ 19522-67-9 ]
[ 144511-13-7 ]
6,9-bis<<2-(isopropylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; In pyridine; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate; chloroform;	Example 25 6,9-bis[2-(isopropylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione (10p) A solution of N-isopropylethylenediamine (450 mg, 4.5 mmol) in pyridine (2 ml) was added to compound 9 (110 mg, 0.45 mmol) in pyridine (1 ml). An instantaneous permanganate-like coloration resulted. The mixture was stirred at room temperature for 40 h. The pyridine and excess diamine were removed under a slow nitrogen stream and the residue was placed under vacuum overnight. Chloroform (20 ml) was added followed by ice water. Since the blue coloration appeared int he aqueous layer, this was extracted with chloroform (4 x 25 ml). The combined extracts were dried over MgSO4 and the chloroform removed by rotary evaporation. The resultant blue solid was purified by column chromatography over silica gel using chloroform as the initial eluant followed by gradual changes to 2%, 5%, 10%, 20%, 40% and 50% methanol in chloroform. The desired product was eluted from the column with 50% methanol/49% chloroform/1% ammonium hydroxide. Removal of the eluants led to 56 mg (30%) of the desired product (10p). mp 136-137C. 1H NMR (CDCl3) 11.1 (t, 1H), 11.0 (t, 1H), 9.6 (s, 1H), 8.9 (d, 1H), 8.1 (d, 1H), 7.30 (m, 2H), 3.6 (m, 4H), 3.0 (t, 4H), 2.9 (m, 2H), 1.05 (d, 6H).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

7
[ 121-05-1 ]
[ 144511-13-7 ]
6,9-bis<<2-(diisopropylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; chloroform; water;	Example 6 6,9-Bis[2-[di(sec-propyl)amino]ethyl]amino}benzo[g]isoquinoline-5,10-dione (10c) N,N-diisopropylethylenediamine (588 mg, 4.1 mmol) was added to compound 9 (100 mg, 0.41 mmol) in methanol (1 ml) and water (1 ml). The mixture was allowed to stir at room temperature for 88 h and then poured into ice water. The blue precipitate was recovered by filtration. The solid was purified by column chromatography over silica gel. The initial eluant was chloroform followed by 2% and 20% methanol in chloroform. Concentration of the latter eluants led to 163 mg (81%) of product 10c . mp 134-136C; 1H NMR (CDCl3): 10.95-11.20 (m, 2H), 9.63 (s, 1H), 8.92 (d, 1H), 8.13 (d, 1H), 7.33 (m, 2H), 3.45 (2q, 4H), 3.10 (h, 4H), 2.82 (t, 4H), 1.08 (d, 24H), Anal. Calcd. for C29H43N5O2: C, 70.55; H, 8.78; N, 14.19. Found: C, 69.23; H, 8.71; N, 13.43.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

8
[ 57260-73-8 ]
[ 144511-13-7 ]
[ 144510-94-1 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; water;	Example 10 6,9-Bis[2-[N-(t-butoxycarbonyl)amino]ethyl]amino}benzo[g]isoquinoline-5,10-dione (10g) A solution of 9 (0.10 g, 0.41 mmol) and N-(t-butoxycarbonyl)ethylenediamine (Synth. Comm., (1990), 20 , 2559; 0.65 g, 4.10 mmol) in pyridine (4.0 ml) was stirred at room temperature for 24 hours. Addition of water (20 ml) led to 10g which was filtered, washed with water and dried (0.17 g, 80%), m.p. 213-216C. Crystallization from a CHCl3: CCl4 mixture gave a dark blue solid m.p. 215-216C; 1H NMR (CDCl3) 11.07 (br, 1H), 10.96 (br, 1H), 9.49 (s, 1H), 8.90 (d, 1H), 7.99 (d, 1H), 7.32 (s, 2H), 5.30 (br, 2H), 3.58 (m, 4H), 3.47 (m, 4H), 1.56 (s, 18H); mass spectrum m/z (relative intensity) 525 (100, M+) 339 (51.9), 57 (87.7). Anal. Calcd. for C27H35N5O6: C, 61.70; H, 6.73; N, 13.32. Found: C, 61.18; H, 6.29; N, 12.88.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

9
[ 121492-06-6 ]
[ 144511-13-7 ]
[ 144510-95-2 ]

Yield	Reaction Conditions	Operation in experiment
400 mg (61%)	In pyridine;	Example 11 6,9-Bis[2-(N-t-butoxycarbonyl-N-methylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione (10h) <strong>[144511-13-7]6,9-difluorobenzo[g]isoquinoline-5,10-dione</strong> (0.29 g, 1.18 mmol) was added to a stirred solution of N-(t-butoxycarbonyl)-N-methylethylenediamine (0.824 g, 4.73 mmol) (J. Med. Chem. 1990, 33 , 97) in dry pyridine (5 ml). The reaction mixture was stirred in a nitrogen atmosphere for 24 hours at room temperature and then for further 8 hours at 50C. The solvent was removed under reduced pressure and the blue residue obtained was taken up with CH2Cl2 (50 ml), washed with a 5% NaHCO3 solution (2 x 30 ml) and with water (30 ml). The combined organic phases were dried over Na2SO4 and the solvent evaporated under reduced pressure. The blue residue was purified by column chromatography (silica gel 230-400 mesh, 50 g, eluent CH2Cl2: AcOEt: MeOH 93:5:2) yielding 400 mg (61%) of blue crystals, m.p. 161.5 - 162.5C after recrystallization from CH2Cl2: hexane. 1H NMR (CDCl3) 1.49 (s, 18H); 2.94 (s, 6H); 3.45-3.75 (m, 8H); 7.25-7.55 (m, 2H); 8.12 (d, 1H); 8.95 (d, 1H); 9.62 (s, 1H); 10.95-11.23 (m, 2H, exchangeable with D2O).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

10
[ 141-43-5 ]
[ 144511-13-7 ]
[ 144510-98-5 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

11
[ 111-41-1 ]
[ 144511-13-7 ]
6,9-bis<<2-<(2-hydroxyethyl)amino>ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

12
[ 107-15-3 ]
[ 144511-13-7 ]
[ 144510-96-3 ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

13
[ 109-76-2 ]
[ 144511-13-7 ]
6,9-bis<(3-aminopropyl)amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
290 mg (93%)	In chloroform;	1) Free Amine : A solution of 1,3-diaminopropane (870 mg, 11.76 mmol) in chloroform (3 ml) was added to 9 (300 mg, 1.22 mmol) in chloroform (6 ml). The purple mixture was allowed to stir for 166 hours at room temperature. The mixture was filtered and the salts washed with chloroform. The solvent was removed by rotary evaporation and the residue was placed under vacuum overnight to yield 290 mg (93%) of 12a ; TLC (silica gel, 25% MeOH/75% chloroform/few drops of aq. ammonium hydroxide) indicated one blue spot; m.p. 105C (softens) 112-115C. 1H NMR (DMSO-d6) 11.15 (m, 1H), 11.05 (m, 1H), 9.45 (s, 1H), 8.90 (d, 1H), 8.0 (d, 1H), 7.55 (br s, 2H), 3.55 (br m, 4H), 4.65 (t, 4H), 3.75 (t, 4H), 1.75 (t, 4H). Anal. Calcd. for C19H23N5O2: C, 64.57; H, 6.56; N, 19.81. Found: C, 65.00; H, 6.50; N, 19.78.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 6851 - 6866

14
[ 108-00-9 ]
[ 144511-13-7 ]
6,9-bis<<2-(dimethylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

15
[ 110-60-1 ]
[ 144511-13-7 ]
6,9-bis<(3-aminobutyl)amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform;	1) Free Amine : A solution of 1,4-diaminobutane (960 mg, 10.9 mmol) in chloroform (3 ml) was added to 9 (319 mg, 1.3 mmol) in chloroform (6 ml). The purple reaction mixture was stirred at room temperature for 217 hours (9 days). The precipitate salts were removed by filtration amd the filtrate concentrated under a slow nitrogen stream to yield the free amine 12b (400 mg, 80%); TLC (Silica gel, 25% MeOH/75% CHCl3/few drops of aq. ammonium hydroxide); m.p. 80C, (softens) 90-92C. 1H NMR (DMSO-d6) 11.15 (m, 1H), 11.05 (m, 1H), 9.42 (s, 1H), 8.90 (d, 1H), 8.0 (d, 1H), 7.5 (br s, 2H), 3.45 (m, 4H), 2.60 (m, 4H), 1.70 (m, 4H), 1.45 (m, 4H). Anal. Calcd. for C21H27N5O2: C, 66.12; H, 7.13; N, 18.36. Found: C, 64.26; H, 6.95; N, 17.42.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1
[3]Journal of Medicinal Chemistry,2010,vol. 53,p. 6851 - 6866

16
[ 109-55-7 ]
[ 144511-13-7 ]
6,9-bis<<3-(dimethylamino)propyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; methanol; chloroform; water;	Example 22 6,9-Bis[3-(dimethylamino)propyl]amino}benzo[g]isoquinoline-5,10-dione (12c) A solution of 3-dimethylaminopropylamine (700 mg, 6.9 mmol) in pyridine (2 ml) was added to compound 9 (100 mg, 0.41 mmol) in pyridine (2 ml). The mixture was stirred at room temperature for 120 h. The excess diamine and pyridine were removed under a slow stream of nitrogen gas and the residue placed under vacuum overnight. The residue was added to cold water and extracted with chloroform (4 x 20 ml). The extract was dried over Na2SO4 and concentrated by rotary evaporation. The blue solid was purified by column chromatography over silica gel. The initial eluant was 10% methanol/90% chloroform followed by 25% methanol/75% chloroform. The product was eluted by addition of small amounts of ammonium hydroxide to 25% methanol/75% chloroform. Concentration of these eluants led to 92 mg (55%) of the desired product 12c mp 107-109C. 1H NMR (CDCl3): 11.00-11.20 (2m, 2H), 9.63 (s, 1H), 8.93 (d, 1H), 8.12 (d, 1H), 7.37 (s, 2H), 3.55 (q, 4H), 2.55 (m, 4H), 2.35 (s, 12H), 2.00 (m, 4H).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

17
[ 100-36-7 ]
[ 144511-13-7 ]
6,9-bis<<2-(diethylamino)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine; methanol; (2S)-N-methyl-1-phenylpropan-2-amine hydrate;	Example 5 6,9-Bis[2-(diethylamino)ethyl]amino}benzo[g]isoquinoline-5,10-dione (10b) A solution of N,N-diethylethylenediamine (684 mg, 5.9 mmol) in pyridine (2 ml) was added to 9 (202 mg, 0.82 mmol) in pyridine (2 ml). The purple mixture was stirred at room temperature for 48 hours (TLC analysis at this point showed one blue component: silica gel, 5% MeOH/CHCl3). The excess base and pyridine were removed by evaporation with a slow stream of nitrogen gas. The crude material was then placed under vacuum overnight. Upon addition of ice-water to the residue the solid was collected by filtration and dried (330 mg, 84%); m.p. 142-144C. 1H NMR (CDCl3) 11.10 (t, 1H), 11.00 (t, 1H), 9.60 (s, 1H), 8.92 (d, 1H), 8.10 (d, 1H), 7.25 (m, 3H), 3.50 (m, 1H), 2.82 (m, 1H), 2.35 (m, 3H), 1.10 (m, 12H). Anal. Calcd. for C25H35N5O2: C, 68.62; H, 16.00; N, 7.31. Found: C, 67.95; H, 16.05; N, 7.28.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

18
[ 144511-13-7 ]
[ 145047-55-8 ]

Yield	Reaction Conditions	Operation in experiment
	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;	EXAMPLE 10 A solution of <strong>[144511-13-7]6,9-difluorobenzo[g]isoquinoline-5,10-dione</strong> (0.97 g) in methylene chloride (40 ml) is added in portions to m-chloroperbenzoic acid (1.78 g, titre about 50%). After about 5 hrs at room temperature, more m-chloroperbenzoic acid (0.35 g) is added and the resulting mixture is left at room temperature for overall 22 hrs. The obtained solution is washed with a sodium bicarbonate saturated solution (3 x 20 ml), the combined aqueous phases are re-extracted with methylene chloride (20 ml) and the combined organic phases are finally washed with brine. After drying over sodium sulfate and distilling the solvent under reduced pressure, the obtained residue is recrystallized from methylene chloride, to gave <strong>[144511-13-7]6,9-difluorobenzo[g]isoquinoline-5,10-dione</strong>-2-oxide, in form of a yellow solid, m.p. 250.1-252.3C (0,75 g). 1-NMR (CDCl3delta: 7.58, m, 2H; 8.11, d, 1H; 8.43, dd, 1H; 8.82, dd, 1H.

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP639183,1998,B1

19
[ 144511-13-7 ]
[ 811-93-8 ]
6,9-bis<(2-amino-2,2-dimethylethyl)amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837

20
[ 144511-13-7 ]
[ 929-06-6 ]
6,9-bis<<2-(2-hydroxyethoxy)ethyl>amino>benzo<g>isoquinoline-5,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
140 mg (82%)	With sodium chloride; In pyridine;	Example 19 6,9-Bis[2-(2-hydroxyethoxy)ethyl]amino}benzo[g]isoquinoline-5,10-dione (11c) A solution of 2-(2-aminoethoxy)ethanol (446 mg, 4.25 mmol) in pyridine (1 ml) was added to compound 9 (100 mg, 0.41 mmol) in pyridine (1 ml). The mixture was stirred at room temperature for 45 h. The excess amine and pyridine were removed via a slow stream of nitrogen gas and the residual solid was placed under vacuum overnight. A cold saturated NaCl solution was added to the solid and the product was extracted with chloroform (6 x 25 ml). The extracts were dried over magnesium sulfate and concentrated on the rotary evaporator to yield 140 mg (82%) of product 11c ; mp 97-99C. 1H NMR (CDCl3): 11.15-11.35 (2m, 2H), 9.60 (s, 1H), 8.85 (d, 1H), 8.08 (d, 1H), 7.30 (m, 2H), 3.85 (m, 8H), 3.57-3.75 (2m, 9H), 2.75-3.25 (br s, 1H).

Reference： [1]Journal of Medicinal Chemistry,1994,vol. 37,p. 828 - 837
[2]Patent: EP503537,1992,A1

21
[ 626-60-8 ]
[ 111608-80-1 ]
[ 144511-13-7 ]

Reference： [1]Journal of Fluorine Chemistry,1994,vol. 68,p. 131 - 134

22
[ 188622-59-5 ]
[ 144511-13-7 ]

Reference： [1]Journal of Heterocyclic Chemistry,1997,vol. 34,p. 27 - 32

23
[ 124-41-4 ]
[ 144511-13-7 ]
6-fluoro-9-methoxybenz<g>isoquinoline-5,10-dione [ No CAS ]
6,9-dimethoxybenz<g>isoquinoline-5,10-dione [ No CAS ]
[ 156090-71-0 ]