Background of the Invention By the age of three, virtually every cnild in America has had at least one respiratory infection caused by respiratory syncytial virus ("RSV"). Of the eight million children under the age of five infected by RSV in the United States each year, approximately 5,000 die, another 100,000 are hospitalized, and 2.4 million are treated by a physician.

The availability of effective treatments for RSV infections is limited. A typical treatment for an RSV infection involves the administration of ribavirin (Virazoleo) as an aerosol, which can reduce the severity of lower respiratory infections. However, ribavirin has a low level of efficacy, as well as a variety of undesirable side effects. The treatment of RSV infections with ribavirin is described by C.B. Hall et al., Journal of the American Medical Association, 1983, 249, 2666-2670.

Therefore, a need exists for an effective treatment of RSV infections having high potency, low toxicity, and few side effects. The present invention provides such a treatment.

Summary of the Invention The present invention is directed to benzanthrone and benzanthrone derivative compositions having antiviral activity and to pharmaceutical compositions for the treatment of a viral infection, which comprise a therapeutically

effective amount of at least one benzanthrone or benzanthrone derivative. Preferred benzanthrones and benzanthrone derivatives include 7H-benz[de]anthracen-7-ones and salts thereof of formula, azabenzanthrones and salts thereof of formula II, or formula III,

7H-benz[de]anthracenes and salts thereof of formula IV, and derivatives thereof, where Rl, R2, and R3, are the same or different, and are individually selected from the group consisting of hydrogen, halide, alkyl, nitrile, nitro, alkanoly, benzyl, benzoly, hydroxyl, methylenedioxy, ethylenedioxy, dialkyamino, and cyclic amino; R4 is selected from the group consisting of hydrogen, alkyl, benzyl, benzoly; R5 and R6 are hydrogen or alkyl having one to four carbon atoms, or form a 5- or 6-membered heterocyclic ring with the nitrogen to which they are attached, where the 5- or 6-membered heterocyclic ring is selected from the group consisting of piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; and X and Y are selected from the group consisting of carbon, nitrogen and oxygen.

Preferred antiviral compositions include those containing a 3-substituted benzanthrone or salt thereof of formula wherein R1 is selected from the group consisting of alkyl and aryl sulfonamide, such as CONHSO2CH3, tetrazole, natural and synthetic carbonyl amino acids, such as CO-glycine, CO-asparagine, CO-arginine, CO-tryptophan, CO-leucine, and CO-proline, carbonyl-N-methylpiperazine, amide, halide, hydroxymethyl, methoxymethyl, and carboxylic acids, and those compositions that contain a 3,9-disubstituted benzanthrone or salt thereof of formula or a derivative thereof, wherein Rl and R2 are the same or different, and are individually selected from the group consisting of alkyl and aryl sulfonamide, such as CONHSO2CH3, tetrazole, natural and synthetic carbonyl amino acids, such as CO-glycine, CO-asparagine, CO-arginine, CO-tryptophan, CO-N-methylpiperazine, CO-leucine, and CO-proline, carbonyl-N-methylpiperazine, amide, halide, hydroxymethyl, and carboxylic acid, including CONH2, CN, Br, CO2H, and CO2Na.

Preferred 3,9-disubstituted benzanthrones and salts include those where R1=R2=CO-N-methylpiperazine, Rl=R2=CONH2, Rl=CN and R2=CONH2, R1=CONH2 and R2=Br, Rl=C02H and R2=Br, or Rl=CO2Na and R2=Br.

The most prefered 3-substituted benzanthrones and salts are of formula and the most preferred 3,9-disubstituted benzanthrones and salts are of formula

The invention also relates to a method for the treatment of a viral infection, which comprises administering to a patient having a viral infection a therapeutically effective amount of an antiviral composition comprising at least one of benzanthrone or benzanthrone derivative, where the benzanthrone or benzanthrone is preferably a 7H-benz [de) anthracen-7-one, an azabenzanthrone, a 7H-benz[de)anthracene, or a derivative thereof, as described above. The method of the invention typically comprises mixing the benzanthrone or benzanthrone derivative with a pharmaceutically suitable carrier to facilitate the administration of the antiviral composition. Preferably the benzanthrone and benzanthrone derivative compositions are used to treat RSV infections.

Detailed DescriPtion of the Invention The present invention is directed to compositions comprising benzanthrones and benzanthrone derivatives having antiviral activity, and to a method of treating viral infections, in particular, RSV infections, with compositions comprising benzanthrones and benzanthrone derivatives.

Benzanthrones having antiviral activity include 7H-benz[de]anthracene-7-ones of formula I,

azabenzanthrones of formula II, 7H-benz[deanthracenes of formula IV,

and formula V, and derivative thereof, where Rl, located at one of positions C8 to Cull, R2, located at one of positions Cl to C3, and R3, located at one of positions C4 to C6, are the same or different, and are individually selected from the group consisting of hydrogen, halide, alkyl, nitrile, nitro, alkanoly, benzyl, benzoly, hydroxyl, methylenedioxy, ethylenedioxy, dialkyamino, and cyclic amino; R4 is selected from the group consisting of hydrogen, alkyl, benzyl, benzoly; R5 and R6 when taken individually are selected from the group consisting of hydrogen and alkyl having one to four carbon atoms, or may form a 5- or 6-membered heterocyclic ring with the nitrogen to which they are attached, where the 5- or 6-membered heterocyclic ring is selected from the group consisting of piperidino, pyrrolo, pyrrolidino, morpholino and N-alkylpiperazino having from one to four carbon atoms in the alkyl group; and X and Y are selected from the group consisting of carbon, nitrogen and oxygen.

For the treatment of a patient having a viral infection, e.g., an RSV infection, a composition comprising at least one benzanthrone or benzanthrone derivative having antiviral activity may be administered to the patient by any means known in the art. To facilitate the administration, the benzanthrone composition may be mixed with a suitable pharmaceutical carrier.

Benzanthrones and benzanthrone derivatives may be tested for anti-RSV activity by a variety of methods known in the art. For example, benzanthrones and benzanthrone derivatives may be tested for the ability to disrupt the ability of HEp2 cells acutely infected with RSV (i.e., cells which are infected with a multiplicity of infection of greater than 2) to fuse and cause syncytial formation on a monolayer of an uninfected line of Hep-2 cells. The lower the observed level of fusion, the greater the antiviral activity of the benzanthrone or benzanthrone derivative is determined to be.

Uninfected confluent monolayers of Hep-2 cells are grown in microtiter wells in 3% EMEM (Eagle Minimum Essential Medium w/o L-glutamine [Bio Whittaker Cat. No. 12-125F], with fetal bovine serum [FBS; which had been heat inactivated for 30 minutes at 560C; Bio Whittaker Cat. No. 14-501F) supplemented at 3%, antibiotics (penicillin/streptomycin; Bio Whittaker Cat. No. 17-602E) added at 1%, and glutamine added at 1%.

To prepare Hep2 cells for addition to uninfected cells, cultures of acutely infected Hep2 cells are washed with DPBS (Dulbecco's Phosphate Buffered Saline w/o calcium or magnesium; Bio Whittaker Cat. No. 17-512F), and cell monolayers are removed with Versene (1:5000; Gibco Life Technologies Cat. No. 15040-017). The cells are spun 10 minutes, and resuspended in 3% FBS. Cell counts are performed using a hemacytometer. Persistent cells are added to the uninfected Hep-2 cells.

The antiviral assay may be conducted by, first, removing all media from the wells containing uninfected Hep-2 cells, then adding a benzanthrone or benzanthrone derivative and 100 acutely RSV-infected Hep2 cells per well. Wells are then incubated at 37"C for 48 hours.

After incubation, cells in control wells are checked for fusion centers, media is removed from the wells, followed by addition, to each well, of either Crystal Violet stain or XTT. With regard to Crystal Violet, approximately

50»1 0.25% Crystal Violet stain in methanol are added to each well. The wells are rinsed immediately, to remove excess stain, and allowed to dry. The number of syncytia per well are then counted, using a dissecting microscope.

With regard to XTT (2,3-bis[2-Methoxy-4-nitro-5- sulfophenyl]-2H-tetrazolium-5-carboxyanilide inner salt), 50p1 XTT (lmg/ml in RPMI buffered with 100mM HEPES, pH 7.2-7.4, plus 5% DMSO) are added to each well. The OD4so/6go is measured (after blanking against growth medium without cells or reagents, and against reagents) according to standard procedures.

Anti-RSV activity cGn also be assayed in vivo via well known mouse models. For example, RSV can be administered intranasally to mice of various inbred strains.

Virus replicates in lungs of all strains, but the highest titers are obtained in P/N, C57L/N and DBA/2N mice.

Infection of BALB/c mice produces an asymptomatic bronchiolitis characterized by lymphocytic infiltrates and pulmonary virus titers of 104 to 105 pfu/g of lung tissue (Taylor, G. et al., 1984, Infect. Immun. 43:649-655).

Cotton rat models of RSV are also well known.

Virus replicates to high titer in the nose and lungs of the cotton rat but produces few if any signs of inflammation.

ExamPles The following non-limiting examples are merely illustrative of the preferred embodiments of the present invention, and are not to be construed as limiting the invention, the scope of which is defined by the appended claims.

Benzanthrones and benzanthrone derivatives may be prepared from readily available starting materials. For example, to prepare 3-substituted benzanthrones, 3-bromobenzanthrone is treated with CuCN to provide 3-cyanobenzanthrone. The 3-cyanobenzanthrone is then hydrolyzed with sodium hydroxide to yield 3-carboxylic benzanthrone. The 3-substituted amides of benzanthrones are

prepared by reacting 3-carboxylic benzanthrones with thionyl chloride to yield the acid chloride followed by substitution with corresponding amines.

To prepare amino acid derivatives of 3-carbonybenzanthrones, a mixture of the acyl chloride of benzanthrone-3-carboxylic acid (1 mmol), a suitable amino derivative (1.1 mmol), such as , e.g., aspartic acid or DL-leucine, and potassium carbonate (3 mmol)(freshly tempered at 2000C for 36 hours at reduce pressure, and ground before use) in 50 ml of anhydrous 1,4-dioxane is stirred at reflux temperature, i.e., 102 to 1050C, for 4 hours. After cooling, the solvent is removed under reduced pressure in a rotary evaporator, and 25 ml of water is added. The reaction mixture is then neutralized to a pH of 6 to 7 by the addition of acetic acid. The resulting precipitate is then collected by filtration, washed with 5 ml of cold water, dried, and recrystallized from nitromethane. Yields range from about 36 to about 47 percent.

The 3-tetrazole and methane sulfonamide derivatives of benzanthrones are prepared from a mixture of the acyl chloride of benzanthrone-3-carboxylic acid (1 mmol) and a suitable amino derivative (1.1 mmol), such as , e.g., lH-tetrazole or methane sulfonamide, in 40 ml of anhydrous pyridine, which is stirred at reflux temperature, i.e., 115 to 1170C for 3 hours. After cooling, the is pyridine removed under reduced pressure in a rotary evaporator, and 40 ml of water is added. The resulting precipitate is then collected by filtration, washed with 10 ml of cold water, dried, and recrystallized from nitromethane. Yields range from about 57 to about 61 percent.

The 3,9-substituted benzanthrones are prepared from a mixture of the acyl chloride of benzanthrone-3,9-dicarboxylic acid (1 mmol), a suitable amine, such as, e.g., 0.1 mol ammonium hydroxide or 2.4 mmol N-methyl piperazine, and potassium carbonate (freshly tempered at 2000C for 36 hours at reduce pressure, and ground before use) in 50 ml of anhydrous 1,4-dioxane, which is

stirred at reflux temperature, i.e., 102 to 1050C, for 3.5 hours. After cooling, the solvent is removed under reduced pressure in a rotary evaporator, and 25 ml of water is added.

The resulting precipitate is then collected by filtration, washed with 5 ml of cold water, dried, and recrystallized from N,N-dimethylformamide. Yields range from about 33 to about 42 percent.

The antiviral properties of a number of benzanthrone compositions were determined by tests using ELISA (Enzyme-linked Immunosorbent Assay), RSV plaque reduction assay, and RSV infectious center assay.

Cytotoxicity was determined by test using XTT (2, 3-bis [2-methoxy-4-nitro-5-sulfophenyl -2H-tetrazolium- 5-carboxanilide inner salt) assay. Results of the tests of the indicated compositions are provided below as percent inhibition for ELISA assay, and ECs0 (ug/ml).

3-Substituted Benzanthrones and Their Salts Structures EC50 (µg/ml) R= H 0.86 Br 0.71 I 0.36 CN 0.1 CO2H 0.45 CO2Na 2.7 CO-N-methlypiperazine 1.0 CONH(CH2)3CH3 3.4 CO-N-morpholine 1.48 CONH2 0.04 CONHCH3 0.44 CO-N-piperidine 2.7

CONHCH2CH2-Ph-m-OCH3 1.36 CONH(CH2)3CO2H 0.47 CONEt2 1.46 COOCH3 0.17 CONHCH(CH3)Ph 1.8 CONH-c-NCOCH2C(CH3)2CH2CO 0.95 CONH(CH2)3-Imidazole 1.3 COO(CH2)2OEt 0.9 CONH-2-pyridine 1.8 CONHOCH3 0.7 CONHCH (CH3) CH2CO2H 1.0 CONHNHCO2CH3 3.4 CONHCH2CH2-2-pyridine 0.8 CONHSO2CH3 0.3 Tetrazole 1.0 CO-glycine 16 CO-asparagine 42 CO-arginine 2.5 CO-tryptophan 9.3 CO-leucine 0.6 CO-proline 2.2 3,9-Disubstituted Benzanthrones Structures EC50 (uq/ml) R1=R2=Br 18.5 R1=R2=CN 1.3 R1=H, R2=SO3Na 4.4 R1=Br, R2=SO3Na 0.56 R1=R2=CO2H 70 Rl=R2=CO2Na 35 R1=R2=CO-N-methylpiperazine 0.03 R1=R2=CONH2 0.04 R1=CN, R2=CONH2 0.23 R1=CONH2, R2=Br 0.03 Rl=CO2H, R2=Br 0.2 R1=CO2Na, R2=Br 0.6

3-Azabenzanthrones and Their Salts Structures ECso (uq/ml) R1=N=pyridinium salt, R2=H 18 Rl=NH2 R2=H 0.08 R1=NHCOCH3, R2=H 15 R1=NHCOPh, R2=H 57 Psridvlbenzanthrone and Its Salts Structures EC50 (µg/ml) R=H 0.03 The preparation and analysis of various compounds useful in the present invention are provided in the following examples.

EXAMPLE 1 3-Methoxy-benz(de)anthracen-7-one A suspension of 3-bromo-benz(de)anthracen-7-one (1.0 g, 0.3 mmol) in 100 ml of methyl alcohol and potassium hydroxide (1.68 g, 3 mmol) was stirred at the reflux temperature for 96 hours. After cooling the methyl alcohol was removed under reduced pressure, 100 ml of water was added, and the resulting mixture was neutralized by the addition of glacial acetic acid. The precipitate was collected by filtration, washed in 25 ml of water, recrystallized from nitromethane, and dried.

Yield = 0.54 g (90%). C18Hl202 m/z - 260 (m+) IR (KBr): 2844, 1734, 1652, 1579, 1285, 746 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 4.12 (s, 3H, 0-CH3), 7.27 (d, 1H, J=8.0 Hz), 7.57 (dd, 1H, J=8.0, 1.5 Hz), 7.80-7.93 (m. 3H), 8.32 (dd, 1H, J=8.0, 1.0 Hz), 8.53 (d, lH, J=8.5 Hz), 8.66-8.73 (m, 2H).

EXAMPLE 2 3-Cyano-benz(de)anthracene-7-one A suspension of 3-bromo-benz(de)anthracene-7-one (2.0 g, 0.65 mmol) in phenylacetonitrile (30 ml) with cuprous cyanide (1.0 g, 1.1 mmol) was heated at 2650C for 7.5 hours, and cooled to OOC. The separated solid was collected, washed with 2-propanol (50 ml), repeatedly boiled with dilute nitric acid (200 ml) to remove copper salts, washed with 100 ml of water, recrystallized from glacial acetic acid and nitrobenzene, and dried.

Yield = 1.27g (77%). C18HgNO2 m/z - 255 (m+) IR (KBr): 3485, 2223, 1660, 1326, 780 cm1.

1H NMR(300 MHz, DMSO-d6, TMS): 6 (ppm) 7.74 (t, 1H, J=8.0 Hz), 7.92 (t, 1H, J=8.0 Hz), 8.13 (dd, 1H, J=8.0, 1.0 Hz), 8.38

(d, 1H, J=8.0 Hz), 8.48 (d, 1H, J=8.0 Hz), 8.55 (d, 1H, J=8.0 Hz), 8.65-8.71 (m, 2H), 8.84 (d, 1H, J=8.0 Hz).

EXAMPLE 3 Benz (de) anthracene-7-one-3-carboxylic acid A mixture of 3-cyano-benz(de)anthracene-7-one (3.0 g, 1.2 mmol), glacial acetic acid (60 ml), and 50% sulfuric acid (48 ml) was stirred at the reflux temperature of 1500C for 16 hours. The reaction mixture was cooled to 600C, and treated with sodium nitrite (1.69 g, 2.54 mmol) over a 1 hour period with rapid stirring to decompose any amide. After cooling the reaction mixture to OOC, the carboxylic acid was precipitated with water (250 ml), recrystallized from glacial acetic acid and nitrobenzene, and dried to give a 2.65 g (82%) yield of the compound in the form of pale lemon-yellow needles. C18Hl003 m/z - 274 (mt) IR (KBr): 3274, 1687, 1668, 1512, 1276, 758 cm1.

1H NMR( 300 MHz, DMSO-d6, TMS): S (ppm) 7.72 (dd, 1H, J=8.0, 1.0 Hz), 7.90 (dd, 1H, J=8.0, 1.0 Hz), 8.02 (dd, 1H, J=8.0, 1.0 Hz), 8.37 (dd, 2H, J=8.0, 1.5 Hz), 8.66 - 8.71 (m, 2H), 8.45 (d, 1H, J=8.0 Hz), 9.35 (d, 1H, J=8.0 Hz).

The conversion to the sodium salt of 7-oxo-benz(de)anthracene-3-carboxylic acid yielded a yellow solid, which was recrystallized from water to provide an analytical sample. mp >3600C Analysis: Cal. for C18H903Na x 1.5 H2O: C, 66.87; H, 3.74%.

Found: C, 66.61; H, 3.585. m/z - 296 (m*) IR (KBr): 3502, 1652, 1600, 1558, 1378, 1279, 771 cm1.

1H NMR ( 300 MHz, DMSO-d6, TMS): S (ppm) 7.645 (t, 1H, J=8.0 Hz), 7.832 (dt, 1H, J=8.0, 1.5 Hz), 7.858 (dt, 1H, J=8.0, 1.5 Hz), 7.93 (d, 1H, J=8.0 Hz), 8.34 (dd, 1H, J=8.0, 1.0 Hz), 8.59 (dd, 1H, J=8.0, 1.0 Hz), 8.62 (d, 1H,

J=8.0 Hz), 8.69 (d, 1H, J=8.0 Hz), 9.50 (dd, 1H, J=8.0, 1.5 Hz).

EXAMPLE 4 7-Oxo-benz (de) anthracene-3-carbonyl chloride A suspension of 7-oxo-benz(de)ahthracene-3-carboxylic acid (2.7 g, 1 mmol) in benzene (70 ml) with thionyl chloride (3.6 ml, 5 mmol) and one drop of N,N-dimethylformamide was heated at the reflux temperature of 950C for 5 hours. After cooling, the solvent was removed under reduced pressure, added benzene was added in three 25 ml aliquots and removed, and 70 ml of hexane was added. The precipitate was collected by filtration, washed with 20 ml of hexane, and dried.

Yield = 2.81 g (96.2%), yellow needles. Cl8HgO2C m/z - 292 (m*) EXAMPLE 5 3 -Hydroxymethyl-benz (de) anthracene-7-one A mixture of 7-oxo-benz(de)anthracene-3-carbonyl chloride (2.93 g, 1 mmol), ethyl acetate (400 ml), and sodium borohydride (1.89 g, 5 mmol) was stirred at room temperature for 24 hours. Then 30 ml of 5% hydrochloric acid was added.

The product was separated with ethyl acetate, washed with water, dried with sodium sulfate, and the solvent was removed under the reduced pressure.

Yield = 1.1 g(42%). Recrystallized from nitromethane.

C18H12O2 m/z - 260 (mt) IR (KBr): 3280, 1684, 1648, 1559, 1280, 1017, 774 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 5.12 (d, 2H, -CH2-, J=7.0 Hz), 5.57 (m, 1H -OH), 7.64 (t, 1H, J=8.0 Hz), 7.836-7.956 (m, 3H), 8.34 (dd, 1H, J=8.0, 1.0 Hz), 8.61-8.67 (m, 3H), 8.75 ( d, 1H, J=8.0 Hz). mp 1990C

Analysis: Calcd. for C18H12O2 x 0.1 H2O: C, 82.48; H, 4.62 %.

Found: C, 82.39; H, 4.71 %.

EXAMPLE 6 3-Methyl-benz(de)anthracene-7-one and a-[7-oxo-benz(de)anthracen-3-yl]-methyl acetate A mixture of 3-hydroxymethyl-benz(de)anthracene-7-one (0.26 g, 0.1 mmol), N,N,-dimethylformamide (40 ml), potassium carbonate (0.414 g, 0.3 mmol) and bromomethyl acetate (0.23g, 0.15 mmol) was stirred at 1600C for 4 hours. After cooling the reaction mixture, N,N,-dimethylformamide was removed under reduced pressure, water (25 ml) was added. The precipitate was collected by filtration, washed with water (15 ml), and dried. Yield = 0.14g (57%).

The sample was further purified with thin layer chromatography (TLC) on silica gel GF (2000 mic) using hexane/ethyl acetate (8:2) as eluant to give the 3-methyl-benz(de)anthracene-7-one and 7-oxo-[benz(de)anthracene-3-yl] methyl acetate.

3-Methyl-benz (de) anthracene-7-one: Cl8Hl2O m/z - 244 (mt) IR (KBr): 3128, 1646, 1580, 1277, 772 cm~l.

H NMR (300 MHz, CDCl3, TMS): 6 (ppm) 2.82 (s, 3H, CH3-), 7.53 (dt, 2H, J=8.0, 1.5 Hz), 7.74 (dd, 1H, J=8.0, 1.0 Hz), 7.82 (t, 1H, J=8.0), 8.31-8.37 (m, 2H), 8.46 (d, 1H, J=8.0 Hz), 8.5 (dd, 1H, J=8.0, 1.0 Hz), 8.8 (d, 1H, J=8.0 Hz).

7-Oxo-[benz(de)anthracene-3-yl]methyl acetate C20H14O3 m/z - 302 (m*) IR (KBr): 3388, 1739, 1658, 1299, 1046, 776 cm-1.

H NMR (300 MHz, CDCl3, TMS): S (ppm) 2.14 (s, 3H, -CH3), 5.62 (s, 2H, -CH2-), 7.55 (t, 1H, J=8.0 Hz), 7.69-7.84 (m, 3H), 8.25-8.39 (m, 3H), 8.47 (dd, 1H, J=8.0, 1.0), 8.75 (d, 1H, J=8.0).

EXAMPLE 7 3-Chloromethyl-benz (de) anthracene-7-one A mixture of 3-hydroxymethyl-benz(de)anthracene-7-one (0.lg, 0.04 mmol), benzene (60 ml), thionyl chloride (0.05 ml, 0.07 mmol), and one drop of pyridine was stirred at the ref lux temperature for 4 hours. After cooling, the solvent was removed under the reduced pressure, 2 15 ml aliquots of benzene were added and removed, and water (15 ml) was added.

The precipitate was collected by filtration, washed with water (10 ml), recrystallized from nitromethane, and dried.

Yield = 0.09g (85%), Cl8HllOC m/z - 278 (m@) IR (KBr): 3032, 1652, 1529, 1456, 961, 773, 703 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 5.42 (s, 2H, -CH2-), 7.67 (dt, 1H, J=8.0, 1.5 Hz), 7.86-8.04 (m, 3H), 8.35 (dd, 1H, J=8.0, 1.0 Hz), 8.63-8.78 (m, 4H).

EXAMPLE 8 3- (4-Methylpiperazinyl)methyl-benz (de) anthracene-7-one A solution of 3-chloromethyl-benz(de)anthracene-7-one (0.05 g, 0.018 mmol) in 1,4-dioxane (70 ml) with N-methylpiperazine (0.02 g, 0.02 mmol) and potassium carbonate (0.07 g, 0.05 mmol) was stirred at 1050C for 3 hours. After cooling, the solvent was removed under the reduced pressure, water (10 ml) was added, and the precipitate was collected by filtration, washed with water, recrystallized from nitromethane, and dried, producing yellow crystals.

Yield = 0.041g, (68%), C23H22N2O m/z - 342 (met) IR (KBr): 2935, 2433, 2363, 1647, 1576, 776, 697 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 2.14 (s, 3H, N-CH3), 2.31-2.45 (m, 8H, aliphatic.), 4.00 (s, 2H, -CH2-), 7.64 (t, 1H, J=8.0 Hz), 7.74 (d, 1H, J=6.0 Hz), 7.85-7.96 (m, 2H), 8.34 (dd, 1H, J=8.0, 1.0 Hz), 8.61-8.73 (m, 3H), 8.83 (d, 1H, J=7.0 Hz).

Conversion to the hydrochloride yielded a yellow solid: C23H23C lN2O m/z - 342 (m+ -36) IR (KBr): 2903, 2334, 1648, 1559, 1419, 1279, 851, 754 cm-1.

EXAMPLE 9 3-Methoxymethyl-benz(de)anthracene-7-one A mixture of 3-chloromethyl-benz(de)anthracene(0.278 g, 0.1 mmol), methyl alcohol (60 ml), and potassium hydroxide (1.12 g, 0.2 mmol) was stirred at reflux temperature for 4 hours. After cooling, the solvent was removed under reduced pressure, water (15 ml) was added, and the reaction mixture was neutralized with acetic acid (pH=7). The precipitate was filtered, washed with water, and dried.

Yield = 0.llg (40%). Further purification with TLC on silica gel GF (1000 mic) using chloroform/methyl alcohol (9:1) as eluant was performed to give the analytically pure compound.

C19H14O2 m/z - 274 (m+) IR (KBr): 3649, 2807, 1653, 1576, 778, 749 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 3.43 (s, 3H, O-CH3), 5.00 (s, 2H, -CH2-), 7.65 (t, 1H, J=8.0, 1.5 Hz), 7.80-7.94 (m, 4H.), 8.35 (dd, 1H, J=8.0, 1.0 Hz), 8.59-8.67 (m, 2H), 8.73 (d, 1H, J=8.0 Hz).

3-{[2-(2-Pyrrolidinylethoxy)ethoxy]methyl}-benz(de) anthracene-7-one was also prepared in a similar manner from 3-chloromethyl-benz(de)anthracene-7-one, and purified with TLC on silica gel GF (1000 mic) using benzene as the eluant to give the analytically pure compound. C26H27NO3 m/z - 401 (m+) IR (KBr): 3649, 2963, 1646, 1559, 1386, 1323, 1277, 1006, 772, 695 cm1.

1H NMR (300 MHz, DMSO-d , TMS): 6 (ppm) 1.69-1.77 (m, 2H), 2.58-2.62 (t, 2H, J=4.0 Hz), 3.47-3.59 (m, 4H), 4.2 (d, 2H, J=6.0 Hz, -CH2-), 7.66-7.77 (m, 2H), 7.92 (t, 1H, J=8.0 Hz),

8.01 (t, 1H, J=8.0 Hz), 8.40 (dd, 1H, J=8.0, 1.0 Hz), 8.67 (d, 2H, J=8.0 Hz), 8.74 (d, 2h, J=8.0 Hz).

EXAMPLE 10 3- (4-Methylpiperazinyl) carbonyl-benz (de) anthracene-7-one A mixture of the 7-oxo-benz(de)anthracene-3-carbonyl chloride (0.293 g, 0.1 mmol), 1,4-dioxane (40 ml), 1-methylpiperazine (0.15 g, 0.15 mmol), and potassium carbonate (freshly tempered at 2000C for 36 hours at reduced pressure, and ground before use) (0.345 g, 0.25 mmol) was stirred at 800C for 2.5 hours. After cooling, the solvent was removed under reduced pressure, water (30 ml) was added, and the reaction mixture was neutralized to a pH of 6 to 7 with acetic acid.

The precipitate was collected with filtration, washed with cold water (15 ml), recrystallized from nitromethane, and dried.

Yield = 0.18g (51%). C23H20N202 m/z-356 (m+) IR (KBr):3335, 2802, 1645, 1622, 1447, 1273, 755 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 2.12 - 2.14 (m, 2H), 2.205(s, 3H, N-CH3), 3.14 - 3.33 (m, 2H), 3.76 - 3.88 (m, 4H), 7.69 (t, 1H, J=8.0, 1.5 Hz), 7.75 (dd, 1H, J=8.0, 1.0 Hz), 7.911 (dt, 1H, J=8.0, 1.0 Hz) ,7.99 (t, 1H, J=8.0, 1.5 Hz), 8.28 (dd, 1H, J=8.0, 1.0 Hz), 8.37 (dd, 1H, J=8.0, 1.0 Hz), 8.68 (dt, 2H, J=9.5, 1.5 Hz), 8.83 (d, 1H, J=8.0, 1.0 Hz). mp 2220C dec.

Analysis: Calcd. for C23H20N2O2 x 0.2 H2O: C, 76.73; H, 5.60; N, 7.74 %. Found: C,76.87; H, 5.90; N, 7.52 %.

Conversion to the hydrochloride yielded a yellow solid.

C23H21C1N2O2 1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 2.80 (s, 3H, N-CH3), 3.21 - 3.52 (m, 4H), 4.76 - 4.79 (m, 2H), 7.70 (t, 1H, J=8.0 Hz), 7.85 (dd, 1H, J=8.0, 1.0 Hz), 7.92 (dt, 2H, J=8.0, 1.5 Hz), 7.99 (dt, lH, J=8.0, 1.5 Hz), 8.38 (dd, 1H, J=8.0, 1.0 Hz), 8.71 (dd, 2H, J=8.0, 1.5 Hz), 8.87 (d, 1H, J=8.0 Hz).

EXAMPLE 11 The following compounds were prepared from the appropriate reactants using the procedure of Example 10.

The compounds prepared in Example 11 are provided in the accompanying Table.

Table for Example 11 Solvent for Yield% m/z (m+) Formula recrystalization CONH2 DMF 55 273 C18H11NO2 CONHCH3 CH3NO2 52 287 C19H13NO2 CONH(CH2)3CH3 CH3NO2 73 329 C22H19NO2 CON(C2H5)2 CH3CN 63 329 C22H19NO2 COOCH3 CH3CN 52 288 C19H12O3 CONHOCH3 CH3NO2 89 303 CONHNHCO2CH3 CH3NO2 84 346 C20H14N2O4 CO-N-morpholine CH3CN 78 343 C22H17NO3 CO-N-piperidine CH3CN 88 341 C23H19NO2 CONHCH2CH2-Ph-m-OCH3 CH3NO2 76 407 C27H21NO3 CONH(CH2)3CO2H CH3COOH 33 359 C22H17NO4 CONHCH(CH3)Ph CH3CN 53 377 C26H19NO2 CONCOCH2C(CH3)2CH2CO CH3NO2 50 397 C25H19NO4 CON(CH2)3-1-imidazole CH3CN 66 381 C24H19N3O2 COO(CH2)2OC2H5 CH3CN 35 346 C22H18O4 CONH-2-pyridine CH3NO2 94 350 C23H14N2O2 CONHCH2CH2-2-pyridine CH3NO2 56 378 C25H18N2O2 CONHCH(CH3)CH2COOH CH3COOH 70 359 C22H17NO4 COOCH2CH(NH2)COOC2H5 CH3NO2 28 389 C23H19NO5 CONHCH(COOH)CH2CH(CH3)2 CH3NO2 36 387 C24H21NO4 CONHCH2COOC2H5 CH3NO2 45 359 C22H17NO4 CONHCH(COOH)CH2COOH CH3NO2 47 390* C22H15NO6 CONHCH(COOH)CH2COOCH3 CH3NO2 58 403 C23H17NO6 CONHCH(COOK)CH2COOK CH3CN 34 466* C22H13NO6K2 CONHCH(COOCH3)CH2-3-indole CH3NO2 60 474 C30H22N2O4 CONHCH(COO-n-C4H9)CH2C6H5 CH3NO2 23 477 C31H27NO4 CONHCH(COOH)CH(CH3)2 CH3NO2 8 374* C23H19NO4 CONHCH(COOC2H5)CH2C6H4-p-OH CH3NO2 43 466* C29H23NO5 CONHCH(COONa)CH2CH2COONa CH3NO2 34 466** C23H15NO6Na2 CONHCH(COOC2H5)CH2CH3SCH3 CH3NO2 53 433 C25H23NO4S CO-1-pyrrolidine-2-COOCH3 CH3NO2 40 385 C24H19NO4 * (m+ +1), ** (m+-1)

a-[(7-Oxo-benz(de)anthracen-3-yl)carbonylamino]-propane-1,3- dicarboxylic acid sodium salt was prepared from the appropriate reactants following the procedure of Example 10 with using dry sodium carbonate.

An analysis of several of the compounds produced in Example 11 is set forth below.

R = CONH2, mp 2930C.

Analysis: Calcd. for ClsHllNO2 x 0.1 H2O: C, 78.58; H, 4.03; N, 5.04 %. Found: C, 78.51; H, 4.21; N, 5.28 %.

R=CONH(CH2)3CH3, mp 192°C.

Analysis: Calcd. for C22HlgNO2 C, 80.21; H, 5.81; N, 4.25 %.

Found: C, 80.13; H, 5.83; N, 4.23 %.

R=CONHCH2CH2-Ph-m-OCH3, mp 171 OC.

Analysis: Calcd. for C27H21NO3: C, 79.58; H, 5.20; N, 3.44 %.

Found: C, 79.41; H, 5.23; N, 3.40 %.

R=CONHCH(CH3)Ph, mp 224°C.

Analysis: Calcd. for C26HlgNO2 C, 82.73; H, 5.07; N, 3.71 %.

Found: C, 82.46; H, 5.12; N, 3.68 %.

R=CONHCH(COOH)CH2CH(CH3)2, mp 158 to 164°C.

Analysis: Calcd. for C24H21NO4 x 0.2 H2O: C, 73.72; H, 5.41; N, 3.58 %. Found: C, 73.54; H, 5.44; N, 3.60 %.

R=CONHCH(COOCH3)CH2-3-indole, mp 138 to 141°C.

Analysis: Calcd. for C30H22N2O4 x 0.2 H2O: C, 75.36; H, 4.63; N, 5.86 %. Found: C, 75.20; H, 4.59; N, 5.87 %.

EXAMPLE 12 3-(2H-2,3,4,5-Tetrazolyl)carbonyl-benz(de)anthracene-7-one A mixture of 7-oxo-benz(de)anthracene-3-carbonyl chloride (0.293 g, 0.1 mmol), lH-tetrazole (0.077g, 0.11 mmol), and dry pyridine (40 ml) was stirred at the reflux temperature

(1150C) for 3 hours. After cooling, the pyridine was removed under reduced pressure, water (40 ml) was added, and the precipitate was collected by filtration, washed with cold water (10 ml), recrystallized from nitromethane, and dried.

Yield = 0.186g (57%). C19H10N4O2 m/z - 326 (m+) IR (KBr): 3097, 1651, 1595, 1281, 781 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 7.72 (t, 1H, J=8.0 Hz), 7.92 (t, 1H, J=8.0 Hz), 8.08 (t, 1H., J=8.0), 8.34 -8.42 (m, 2H), 8.65 - 8.73 (m, 3H), 8.89 (d, 1H, J=8.0 Hz), 9.57 (dd, 1H, J=8.0, 1.0 Hz).

EXAMPLE 13 N-(Methylsulfonyl)-[7-oxo-benz(de)anthracen-3yl)formamide was prepared using the procedure of Example 12 from 7-oxo-benz (de) anthracene-3-carbonyl chloride, and recrystallized from nitromethane.

Yield=0.214 g (61%). C19H13NO4S m/z - 351 (m+) 1H NMR (300 Mhz, DMSO-d6, TMS): 6 (ppm) 3.74 (s, 3H, CH3), 7.68 (t, 1H, J=8.0 Hz), 7.88 (dt, 2H, J=12.0, 1.5 Hz), 8.10 (d, 1H, J=8.0 Hz), 8.39 (d, 1H, J=8.0 Hz), 8.45 (d, 1H, J=8.0 Hz), 8.54 (d, 1H, J=8.0 Hz), 8.79 (d, 1H, J=8.0 Hz), 8.84 (d, 1H, J=8.0 Hz).

N-[(4-Methylphenyl)sulfonul]-[7-oxo-benz(de)anthracen-3-y l] formamide was prepared in a similar manner from 7-oxo-benz (de) anthracene-3-carbonyl chloride, and recrystallized from nitromethane.

Yield=0.31 g (72.5%). C25H17NO4S m/z - 427 (m+) IR(KBr): 3195, 1698, 1630, 1574, 1430, 1347, 1159, 1057, 781, 547 cm~l.

1H NMR (300 Mhz, DMSO-d6, TMS): 6 (ppm) 2.46 (s, 3H, -CH3), 7.54 (d, 2H, J=8.0 Hz), 7.71 (t, 1H, J=8.0 Hz), 7.88 - 8.03

(m, 5H), 8.32 - 8.36 (m, 2H), 8.66 (dt, 2H, J=12.0, 1.5 Hz), 8.82 (d, 1H, J=8.0 Hz0.

Example 14 7-Oxo-benz(de)anthracene-9-sulfonic acid, sodium salt A mixture of benz(de)anthracene-7-one (25 g, 0.109 mol) and fuming sulfuric acid (5% of SO3) (250 g) was heated at 145 to 1500C for 2 hours, cooled, and poured into ice (600 g).

Unreacted benz(de)ahtracene-7-one was removed with filtration, and sodium carbonate (750 g) was added with stirring at 800C. The reaction mixture was made up to 51 by the addition of a saturated salt solution, boiled, and allowed to cool. The crystalline sodium salt of the sulphonic acid (37 g) separated, and was collected, washed with salt solution, and purified with four recrystallizations from hot water from which it separated as a green-yellow crystalline powder.

Yield = 5 g (14%). Cl7HgNaO4S m/z - 332 (m+) IR (KBr): 3446, 1648, 1597, 1195, 1042, 632 cm~l. lH NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 7.66 (t, 1H, J=8.0 Hz), 7.82-7.96 (m, 2H), 8.04 (dd, 1H, J=8.0, 1.0 Hz), 8.26 (d, 1H, J=6.0 Hz), 8.51 (d, 1H, J=6.0 Hz), 8.59-8.81 (m, 2H), 9.39 (dd, 1H, J=7.0, 1.0 Hz).

EXAMPLE 15 3-Nitro-benz(de)anthracene-7-one 88% nitric acid (2.7 ml, 5.6 mmol) was added dropwise to a solution of benz(de)anthracene-7-one (log, 4.35 mmol) in nitrobenzene (80 ml) at 18 to 200C. The reaction mixture was stirred at 500C for 3 hours, and the yellow precipitate was filtered off, washed with nitrobenzene, reczystallized with chlorobenzene, and dried.

Yield = 8.4 g (70%). Cl7HgNO3 m/z - 275 (m+)

IR (KBr): 1684, 1540, 1456, 1305, 777 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): S (ppm) 7.75 (t, 1H, J=8.0 Hz), 7.93 (dt, 1H, J=8.0, 1.0 Hz), 8.09 (dt, 1H, J=8.0, 1.0 Hz), 8.33 (dd, 1H, J=8.0, 1.0 Hz), 8.49 (d, 1H, J=8.0 Hz), 8.65 (d, 1H, J=8.0 Hz), 8.69 (d, 1H, J=8.0 Hz), 8.78 (d, 1H, J=8.0 Hz), 8.87 (d, 1H, J=8.0 Hz), EXAMPLE 16 3-Amino-benz (de) anthracene-7-one 3-nitro-benz(de)anthracene-7-one (6 g, 2.1 mmol) was added to an aqueous solution of sodium sulfide (10 g, 4.2 mmol) in water (50 ml). The resulting suspension was stirred initially at 18 at 200C for 1.5 hours and then at boiling point for 4 hours. The red precipitate was filtered from the hot reaction mixture, and washed on a filter to a neutral reaction (pH=7) with water, recrystallized from chlorobenzene, and dried to provide the compound in the form of yellow needles.

Yield = 4.3 g (83.5%). C17H11NO m/z - 245 (m+) IR (KBr): 2808, 1734, 1636, 1559, 1316, 773 cm-1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 6.90 (m, 2H, - NH2), 7.42 (t, 2H, J=8.0 Hz), 7.71-7.80 (m, 2H), 8.28 (dd, 1H, J=8.0, 1.0 Hz), 8.40 (d, 1H, J=8.0 Hz), 8.48 (d, 1H, J=8.0 Hz), 8.67 (d, 1H, J=8.0 Hz), 8.74 (d, 1H, J=8.0 Hz).

EXAMPLE 17 3-Iodo-benz (de) anthracene-7-one Sodium nitrite (0.14 g, 0.2 mmol) was added to a solution of 3-amino-benz(de)anthracene-7-one (0.25 g, 0.1 mmol) in 96% sulfuric acid (10 g), and stirred at 50C at 50C for 0.5 hour.

A mixture of water (50 ml) and ice(50 g) was then added. A solution of sodium iodide (0.6 g, 0.4 mmol) in water (5 ml) was added to the stirred red reaction mixture, which was heated at 35 to 400C for 1 hour. The mixture was cooled, and

the precipitate was filtered off, washed with water, recrystallized from chlorobenzene, and dried, providing yellow crystals.

Yield = 0.14 g (57%). . C17H9IO m/z - 356 (m+) 1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.66 (t, 1H, J=8.0, 1.5 Hz), 7.86 (dt, 1H, J=8.0, 1.5 Hz), 7.98 (t, 1H, J=8.0, 1.5 Hz), 8.32 (dd, 1H, J=8.0, 1.0 Hz), 8.39 (d, 1H, J=8.0 Hz), 8.45 (d, 1H, J=8.0 Hz), 8.49 (dd, 1H, J=8.0, 1.0 Hz), 8.58 (d, 1H, J=8.0 Hz), 8.67 (dd, 1H, J=8.0, 1.0 Hz) EXAMPLE 18 N- (7-Oxo-benz (de) anthracen-3-yl) -ethanamide 3-Amino-benz(de)anthracene (2.4 g, 1.0 mmol) was dissolved in boiling glacial acetic acid (70 ml), and a solution of acetic anhydride (7 ml, 7.4 mmol) was added to the resulting mixture, which was boiled for 1 hour. After cooling, the acetic acid was removed under the reduced pressure, water (50 ml) was added, and the precipitate was collected by filtration, washed with acetone, recrystallized from N,N-dimethylformamide, and dried.

Yield = 1.17 g (45%). C19H13N02 m/z - 287 (m+) IR (KBr): 3265, 1683, 1657, 1539, 1306, 779 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 2.27 (s, 3H, -CH2), 7.62 (t, 1H, J=8.0 Hz), 7.87 (dt, 1H, J=8.0, 1.0 Hz), 7.96 (t, 1H, J=8.0 Hz), 8.13 (d, 1H, J=8.0 Hz), 8.34 (dd, 1H, J=8.0, 1.0 Hz). 8.59 (dd, 1H, J=8.0, 1.0 Hz), 8.70-8.78 (m, 3H), 10.30 (s, 1H, -NH-).

EXAMPLE 19 <BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> 3-[ (Diethyloxyphosphinyl) methyl] amino-benz (de) anthracene-7-on e Diethylhydrogen phoshite (1.38 g, 1.0 mmol) and paraformaldehyde (0.3 g) were added To a solution of

3-amino-benz(de)anthracene-7-one (2.45 g, 1.0 mmol) in 1.4-dioxane (200 ml). The reaction mixture was boiled for 4 hours. After cooling, 1,4-dioxane was distilled off, and the residue was dissolved in chloroform, filtered, and dried by evaporation.

Yield = 1.5 g (42.8%). C22H22NO4P m/z - 395 (m), m. p. 1490C.

EXAMPLE 20 9-Bromo-3-cyano-benz(de)ahthracene-7-one Bromine (1.0 g, 0.63 mmol) was added to a well stirred suspension of 3-cyano-benz(de)anthracene-7-one (0.51 g, 0.2 mmol) in water (100 ml) at 30 - 400C, and the resulting reaction mixture was heated at 700C for 170 hours. After cooling, the precipitate was collected by filtration, washed with water recrystallized from nitrobenzene, and dried.

Yield = 0.48 g (71.6%). Q8H8BrNO m/z - 335 (m+) H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 8.08 (dd, 1H, J=8.0, 1.0 Hz), 8.14 (d, 1H, J=8.0 Hz), 8.38 (d, 1H, J=8.0 Hz), 8.40 (d, 1H, J=8.0 Hz), 8.58 (dd, 1H, J=8.0, 1.0 Hz), 8.63 (d, 1H, J=8.0 Hz), 8.71 (dd, 1H, J=8.0, 1.0 Hz), 8.86 (dd, 2H, J=8.0, 1.5 Hz) EXAMPLE 21 3,9-Dibromo-benz(de)anthracene-7-one was synthesized from the bromination reaction of 3-bromo-benz(de)anthracene-7-one for 18 hours using the same procedure used for Example 20. The product was recrystallized from nitrobenzene in the form of yellow needles.

Yield = 3.4 g (87.6%), Cl7H8Br2O m/z - 388 (mt) IR (KBr): 1644, 1561, 1373, 1079, 823 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 8.02 (dt, 1H, J=8.0, 1.0 Hz), 8.12 (d, 1H, J=8.0 Hz), 8.31 (d, 1H, J=8.0 Hz), 8.50 (d, 1H, J=8.0 Hz), 8.55-8.66 (m, 4H). mp 2460C Analysis: Calcd. for Cl7H8Br2O: C, 52.61; H, 2.08 %. Found: C, 52.71; H,2.08 %.

The 9-Bromo-7-oxo-benz (de) anthracene-3-carboxamide was prepared from 7-oxo-benz (de) anthracene-3-carboxamide using the bromination reaction procedure of Example 20 for 48 hours with recrystallization from nitrobenzene.

Yield = 0.36 g (47%). C18H10BrNO2 m/z - 351 (m+-1) 1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.87 (s, 1H), 7.91-8.00 (m, 3H), 8.07 (dd, 1H, J=8.0, 1.0 Hz), 8.27 (s, 1H), 8.41 (d, 1H, J=8.0 Hz), 8.64 (d, 1H, J=8.0 Hz), 8.68 (dd, 1H, J=8.0, 1.0 Hz), 8.83 (d, 2H, J=8.0 Hz).

EXAMPLE 22 9-Bromo-7-oxo-benz (de) anthracene-3-carboxylic acid was prepared from 9-bromo-3-cyano-benz (de) anthracene-7-one following the hydrolysis reaction procedure of Example 3 for 48 hours with recrystallization from glacial acetic acid.

Yield = 0.27 g (77%). C18H9BrO3 m/z - 354 (m+1) Conversion to the sodium salt of 9-bromo-7-oxo-benz (de) anthracene-3-carboxylic acid yielded a yellow powder. Cl8H8BrNaO3 EXAMPLE 23 9-Bromo-7-oxo-benz (de) anthracene-3-carbonyl chloride was prepared from 9-bromo-7-oxo-benz (de) anthracene-3-carboxylic acid using the same procedure as used in the Example 4 with recrystallization from m-xylene.

Yield=0.97g (82%). C18HBrClO2

m/z - 371 (m+).

EXAMPLE 24 9-Bromo-3-hydroxymethyl-benz (de) anthracene-7-one was prepared from 9-bromo-7-oxo-benz (de) anthracene-3-carbonyl chloride using the procedure of Example 5 for 32 hours with further purification with TLC on silica gel GF (1000 mic) using chloroform/methanol (9:1) as the eluant.

Yield = 0.15 g (45.5%). C18H11BrO2 m/z - 338 (m+-1) IR (KBr): 3488, 1643, 1575, 1375, 1302, 1055, 815 cm1.

1H NMR (300 MHz, DMSO-d5, TMS): s (ppm) 5.12 (d, 2H, J=4.0 Hz, -CH2-), 5.60 (m, 1H. -OH), 7.86 (d, 1H, J=6.0 Hz), 7.95 (t, 1H, J=8.0 Hz), 8.04 (dd, 1H, J=8.0, 1.0 Hz), 8.40 (d, 1H, J=8.0 Hz), 8.60 (d, 1H, J=8.0 Hz),, 8.64-8.68 (m, 2H), 8.78 (d, 1H, J=8.0 Hz).

EXAMPLE 25 3-Bromo-7-oxo-benz (de) anthracene-9-sulfonic acid sodium salt was prepared from 3-bromo-benz(de)anthracene-7-one using the same procedure used for Example 14 with recrystallization from aqueous ethyl alcohol.

Yield = 3.67 g (23.5%) Cl7H8BrO4SNa m/z - 411(m+) IR (KBr): 3446, 1650, 1501, 1198, 1046, 825, 627 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 8.02-8.07 (m, 3H), 8.16 (d, 1H, J=8.0 Hz), 8.56-8.65 (m, 3H), 8.73 (dd, 1H, J=8.0, 1.0 Hz).

EXAMPLE 26 3-Bromo-6-(2-pyridilamido)-benz(de)anthracene-7-one 3-Bromo-benz(de)anthracene-7one (0.3g, 0.1 mmole) was added to a stirred mixture of the 2-aminopyridine (0.282g, 0.3 mmole) in dry methyl sylfoxide (30 ml) and powdered

potassium hydroxide (1.4g, 2.5 mmole). The reaction mixture was stirred at room temperature for 16 hours, diluted with ice-cold water (100 ml), and adjusted to a pH of 4 to 5 using hydrochloric acid (35%). The product was separated, filtared, washed with water, dried, and purified using TLC on silica gel GF (2000 mic.) with benzene/ethyl acetate (8:2) as the eluant.

Yield= 0.27g (67.5%). C22Hl3BrN2O m/z - 401 (m+) IR(KBr): 3389, 2955, 1648, 1559, 1457, 1296, 1147 cm1.

1H NMR (300 Mhz, DMSO-d6, TMS): 6 (ppm) 7.21 (t, 1H, J=8.0 Hz), 7.35 (d, 1H, J=8.0 Hz), 7.69 (d, 1H, J=8.0 Hz), 7.71 (d, 1H, J=8.0 Hz), 7.90-7.98 (m, 3H), 8.49(dd, 1H, J=8.0, 1.0 Hz), 8.53 (dd, 1H, J=8.0, 1.0 Hz), 8.68 (d, 1H, J=8.0 Hz), 8.70 (d, 1H, J=8.0 Hz), 9.246 (dd, 1H, J=8.0, 1.0 Hz), 14.33 (s, 1H, N-H).

EXAMPLE 27 3,9-Dicyano-benz(de)ahtracene-7-one was prepared from 3,9-dibromo-benz(de)ahthracene-7-one using the procedure of Example 2 with recrystallization from nitrobenzene.

Yield = 0.15 g (53.6%). ClgH8N2O m/z - 280 (m+) IR (KBr): 3070, 2227, 1659, 1577, 1381, 779 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 8.09 (t, 1H, J=8.0 Hz), 8.27 (dd, 1H, J=8.0, 1.0 Hz), 8.39 (d, 1H, J=8.0 Hz), 8.51-8.56 (m, 2H), 8.64 (dd, 1H, J=8.0, 1.0 Hz), 8.77 (d, 1H, J=8.0 Hz), 8.86 (d, 1H, J=8.0 Hz).

EXAMPLE 28 3,9-Di-(2H-2,3,4,5-tetrazolyl)-benz(de)anthracene-7-one A suspension of 3,9-dicyano-benz(de)anthracene-7-one (0.28 g, 0.1 mmol), sodium azide (0.65 g, 1.0 mmol), ammonium chloride (0.54 g, 1.0 mmol) in fresh distilled anhydrous N,N-dimethylformamide was stirred at 1000C for 48 hours.

After cooling, the solvent was removed under reduced pressure, and water (15 ml) was added. The precipitate was collected by filtration, washed with water (10 ml), recrystallized from N,N-dimethylformamide, and dried.

Yield = 0.15 g (41.6%). ClgHloN8O m/z - 366 (m+) IR (KBr): 3528, 3424, 3027, 1653, 1570, 1384, 1311, 1027, 842, 742 cm-l.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 8.00 (dd, 1H, J=8.0, 1.0 Hz), 8.08 (dd, 1H, J=8.0, 1.0 Hz), 8.37 (dd, 1H, J=8.0, 1.0 Hz), 8.44 (dd, 1H, J=8.0, 1.0 Hz), 8. 52 (dt, 1H, J=8.0, 1.0 Hz), 8.70 (dt, 1H, J=8.0, 1.0 Hz), 8.80 (dd, 1H, J=8.0, 1.5 Hz), 8.92 (dt, 1H, J=8.0, 1.0 Hz), 9.54 (d, 2H, -NH-).

EXAMPLE 29 7-Oxo-benz(de)anthracene-3,9-carboxylic acid prepared from 3,9-dicyano-benz(de)anthracene-7-one with the of hydrolysis reaction of Example 3 for a period of 48 hours with recrystallization from glacial acetic acid and nitrobenzene.

Yield = 0.21 g (66%). . C19H10O5 m/z - 317 (m+-1) IR (KBr): 3467, 3151, 1698, 1651, 1604, 1580, 1280, 780 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 7.97 (t, 1H, J=8.0 Hz), 8.05 (t, 1H, J=8.0 Hz), 8.31 (d, 1H, J=8.0 Hz), 8.47 (dd, 1H, J=8.0, 1.0 Hz), 8.61-8.80 (m, 4H).

Conversion to the sodium salt of 7-oxo-benz(de)anthracene-3,9-dicarboxylic acid yielded a yellow powder. C19H8O5Na2 IR (KBr): 3538 - 3082, 1697, 1654, 1601, 1509, 1335, 1278, 784 cm~l.

EXAMPLE 30 3,9-Di-[benz(de)anthracene-7-one]carbonyl chloride was prepared from 7-oxo-benz(de)anthracene-3,9-dicarboxylic acid using the procedure of Example 4 with recrystallization from benzene.

Yield = 2.0 g (88.5%). ClgH8Cl203 m/z - 355 (m+) EXAMPLE 31 3,9-Di-(hydroxymethyl)-benz(de)ahthracene-7-one was synthesized from 3,9-di-[benz(de)anthracene-7-one]carbonyl chloride using the procedure of Example 5 and further purification with TLC on silica gel GF (1000 mic) using chloroform/methanol (9:1) as the eluant to give the analytically pure compound.

Yield = 0.17 g (58.6%). C19H14O3 m/z - 290 (m+) IR (KBr): 3297, 2991, 1650, 1575, 1-49, 780 cm-1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 4.68 (d, 2H, -CH2-, J=4.0 Hz), 5.12 (d, 2H, -CH2-, J=4.0 Hz), 5.45-5.46 (m, 1H, -OH), 5.55-5.56 (m, 1H, -OH), 7.80 (dd, 1H, J=8.0, 1.0 Hz), 7.84 (d, 1H, J=8.0 Hz), 7.93 (t, 1H, J=8.0 Hz), 8.31 (s, 1H), 8.59 (d, 1H, J=8.0 Hz), 8.63 (dd, 1H, J=8.0, 1.0 Hz), 8.66 (dd, 1H, J=8.0, 1.0 Hz), 8.74 (dd, 1H, J=8.0 Hz). mp 167°C dec.

Analysis: Calcd. for C19H14O3 x 0.2 H2O: C, 77.64; H, 4.80 %.

Found: C, 77.49; H, 4.84 %.

EXAMPLE 32 3,9-Di-[7-oxo-benz(de)anthracenyl]carbamide have been prepared from 3,9-di-[benz(de)anthracene-7-one]carbonyl chloride with the procedure of Example 10 with recrystallization from N,N,-dimethylformamide.

Yield = 0.1 g (33%). C19H12N2O3

m/z - 316 (m+) 1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 7.61 (d, 1H, J=8.0 Hz), 7.88-7.96 (m, 2H), 8.07-8.09 (m, 1H), 8.28-8.41 (m, 3H), 8.5 (dd, 1H, J=8.0, 1.0 Hz), 8.667 (dt, 1H, J=8.0, 1.5 Hz), 8.73-8.85 (m, 2H).

EXAMPLE 33 3,9-Di-(4-methylpiperazinyl)carbonyl-benz(de)anthracene-7-on e was prepared from 3,9-di-[benz(de)anthracene-7-one]-carbonyl chloride with the procedure of Example 10 with recrystallization from N, N-dimethylformamide.

Yield = 0.2 g (42%). C29H30N4O3 m/z - 482 (m+) 1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 1.75 (s, 6H, CH3), 2.13-2.43 (m, 8H), 3.42-3.45 (m, 4H), 3.67-3.69 (m, 4H), 7.92 (d, 1H, J=8.0 Hz), 8.13 (t, 1H, J=8.0 Hz), 8.28 (t, 1H, J=8.0 Hz), 8.44 (d, 1H, J=8.0 Hz), 8.58 (d, 1H, J=8.0 Hz), 8.71-8.74 (m, 2H), 8.83 (m, 1H).

EXAMPLE 34 <BR> <BR> <BR> <BR> <BR> <BR> <BR> N-[ (Methylsulfonyl) -9- (methylsulfonyl) carbamoyl-7-oxobenz (de) anthracen-3-yl]formamide was prepared from 3,9-di-[benz(de)anthracene-7-one]carbonyl chloride with the procedure of Example 12 with recrystallization from nitromethane.

Yield = 0.26 g (55%). , C21H16N2O7S2 m/z - 472 (m+) IR (KBr): 3628-3026, 1715, 1699, 1603, 1471, 1383, 1157, 886, 783, 520 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 3.44 (s, 3H, CH3), 3.55 (s, 3H, CH3), 8.06 (t, 1H, J=8.0 Hz), 8.10 (t, 1H, J=8.0 Hz), 8.39 (d, 1H, J=8.0 Hz), 8.72 (d, 1H, J=8.0 Hz), 8.75 (d, 1H, J=8.0 Hz), 8.87 (d, 1H, J=8.0 Hz), 8.92 (d, 1H, J=8.0 Hz), 8.97 (d, 1H, J=8.0 Hz).

EXAMPLE 35 7H-Benz(de)anthracene A mixture of benz(de)anthracene-7-one (0.5 g, 0.22 mmol), 2-propanol (80 ml), and aluminum isopropoxide (4.4 g, 2.2 mmol) was heated at 850C for 20 hours. After cooling, the solvent was removed under the reduced pressure, water (100 ml) was added, and the reaction mixture was acidified with dilute sulfuric acid (pH=l). The product was then extracted with boiling benzene (100 ml), the organic layer was dried with Na2SO4, and the solvent was evaporated to give the compound, which was purified with TLC on silica gel GF (2000 mic) using hexane as the eluant.

Yield = 0.35 g (74 %). Cl7Hl2 m/z- 215 (m+-1) IR (KBr): 2986, 1559, 815, 750 cm1.

1H NMR (300 MHz, CDCl3, TMS): s (ppm) 4.48 (s, 2H, -CH2-), 7.27 (d, 1H, J=8.0, Hz), 7.32-7.51 (m, 5H), 7.67 (d, 1H, J=8.0 Hz), 7.71 (d, 1H, J=8.0 Hz), 8.00 (d, 1H, J=8.0 Hz), 8.03 (d, 1H, J=8.0 Hz). mp 740C Analysis: Calcd. for C17H12: C, 94.40; H, 5.59 %. Found: C, 94.17; H, 5.55 %.

Similarly, the following compounds were prepared from the appropriate reactants: 3-Bromo-7H-benz(de)anthracene. Purification was achieved via TLC on silica gel GF (2000 mic) using hexane as the eluant.

Yield = 1.2 g (81 %). Cl7HllBr m/z- 295 (m+) IR (KBr): 3486, 1490, 1380, 1250, 832, 772 cm1.

1H NMR (300 MHz, CDCl3, TMS): 6 (ppm) 4.57 (s, 2H, -CH2-), 7.31-7.33 (m, 2H), 7.44 (dd, 1H, J=8.0, 1.0 Hz), 7.55 (t, 1H, J=8.0 Hz), 7.78 (d, 1H, J=8.0 Hz), 7.85 (d, 1H, J=8.0 Hz), 8.00 (dd, 2H, J=8.0, 1.5 Hz), 8.07 (d, 1H, J=8.0 Hz). mp 113°C

Analysis: Calcd. for C17H11Br x 1.5 H2O: C, 63.77; H, 3.44 %.

Found: C, 63.61; H, 3.29 %.

3-Cyano-7H-benz(de)anthracene. Purification was achieved via TLC on silica gel GF (2000 mic) using benzene/petroleum ether (1:1) as the eluant.

Yield = 0.16 g (66 %).C18H11N m/z- 240 (m+-l) IR (KBr): 2218, 1559, 773 cm1.

1H NMR (300 MHz, CDCl3, TMS): s (ppm) 4.60 (s, 2H, -CH2-), 7.37-7.39 (m, 3H), 7.51 (dd, 1H, J=8.0, 1.0 Hz), 7.64 (t, 1H, J=8.0 Hz), 7.90 (d, 1H, J=8.0 Hz), 8.01 (d, 1H, J=8.0 Hz), 8.03 (d, lH, J=8.0 Hz), 8.07 (d, lH, J=8.0 Hz).

7H-Benz (de) anthracene-3-carboxylic acid Yield = 0.15 g (57%). Recrystallized from toluene. C18H12O2 m/z- 260 (m+) IR (KBr): 3385, 1684, 1517, 771 cm-1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 4.61 (s, 2H, -CH2-), 7.37-7.44 (m, 2H), 7.53 (dd, lH, J=8.0, 1.0 Hz), 7.64 (d, lH, J=8.0 Hz), 8.16-8.23 (m, 2H), 8.68 (d, lH, J=8.0 Hz), 8.77 (dd, lH, J=8.0, 1.0 Hz), 9.36 (dd, lH, J=8.0, 1.0 Hz).

Conversion to the sodium salt of 7H-benz (de) anthracene-3-carboxylic acid and recrystallized from water to give analytical sample. Cl8HllO2Na 1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 4.52 (s, 2H, -CH2-), 7.25-7.42 (m, 5H), 7.75 (d, lH, J=8.0 Hz), 8.03 (d, 1H, J=8.0 Hz), 8.09 (dd, lH, J=8.0, 1.0 Hz), 8.82 (d, lH, J=8.0 Hz).

3-Hydroxymethyl-7H-benz(de)anthracene. Purification was achieved via TLC on silica gel GF (2000 mic) using hexane/ethyl acetate (1:1) as the eluant.

Yield = 0.11 g (44.7 %). C,8H140 m/z- 246 (m+) IR (KBr): 2923, 1576, 1456, 1094, 772 cm1.

1H NMR (300 MHz, CDCl3, TMS): 6 (ppm) 4.56 (s, 2H, -CH2-), 7.25 (d, 1H, J=8.0 Hz), 7.28 (d, 1H, J=8.0 Hz), 7.30 (dd, 1H, J=8.0, 1.0 Hz), 7.34 (d, 1H, J=8.0 Hz), 7.39 (dd, 1H, J=8.0, 1.0 Hz), 7.48 (d, 1H, J=8.0 Hz), 7.80 (d, 1H, J=8.0 Hz), 7.91 (d, 1H, J=8.0 Hz), 8.01 (d, 1H, J=8.0 Hz).

EXAMPLE 36 7-Methyl-benz(de)anthracen-7-ol Benz(de)anthracene-7-one (5.0 g, 2.2 mmol) was dissolved in dry ether (120 ml). Excess of methyllithium (1.4 M solution in diethyl ether) (50 ml) was added using a hypodermic syringe, and the reaction mixture was stirred overnight at room temperature under an argon atmosphere. The lithium salt of the alcohol was hydrolyzed by dropwise addition of water (50 ml) using a dropping funnel. The alcohol was extracted with ether, and the combined ether extract was dried over Na2SO4. Evaporation of ether yielded the compound, which was recrystallized from carbon tetrachloride.

Yield = 4.4 g, (76%). Cl8Hl4O m/z- 246 (m+) IR (KBr): 3282, 1559, 1081, 761 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 1.46 (s, 3H, -CH3), 6.08 (s, 1H, -OH), 7.39-7.44 (m, 2H), 7.61 (t, 1H, J=8.0 Hz), 7.64 (t, 1H, J=8.0 Hz), 7.87 (d, 1H, J=8.0 Hz), 7.89 (d, 1H, J=8.0 Hz), 7.92 (d, 1H, J=8.0 Hz), 7.97 (dd, 1H, J=8.0, 1.0 Hz), 8.20 (dd, 1H, J=8.0, 1.0 Hz), 8.29 (d, 1H, J=8.0 Hz).

EXAMPLE 37 7-Methylene-benz(de)anthracene Sulfuric acid (10%, 50 ml) was added to a solution of 7-methyl-benz(de)anthracen-7-ol (2.5 g, 1.0 mmol) in ether (125 ml). The reaction mixture was stirred overnight, and the precipitated solid was filtered, washed with water to

remove sulfuric acid, recrystallized from carbon tetrachloride and absolute ethyl alcohol, and dried.

Yield = 1.85 g (81%).Cl8Hl2 m/z- 228 (m+) IR (KBr): 3022, 1576, 778, 749 cm1.

H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 5.32 (dd, lH, J=6.0, 3.0 Hz, =CH2), 5.49 (dd, lH, J=6.0, 3.0 Hz, =CH2), 7.09 (dt, lH, J=8.0 Hz), 7.53 (t, lH, J=8.0 Hz), 7.65 (t, lH, J=8.0 Hz), 7.75 (t, lH, J=8.0 Hz), 7.78 (t lH, J=8.0 Hz), 7.96 (t, lH, J=8.0 Hz), 8.24 (dt, lH, J=8.0, 1.5 Hz), 8.31 (d, lH, J=8.0 Hz), 8.42 (d, lH, J=8.0 Hz), 8.76 (dd, lH, J=8.0, 1.0 Hz), 8.92 (dd, lH, J=8.0, 1.0 Hz).

EXAMPLE 38 7-Hydroxyimino-benz(de)anthracene A mixture of benz(de)anthracene (2.5 g, 1.09 mmol), hydroxylamine hydrochloride (12 g, 17.4 mmol) in dry pyridine (60 ml) was heated at 115°C for 70 to 90 hours. Most of the pyridine was distilled off, and the residue was poured into water (40 ml), and extracted with 3 70 ml aliquots of ether, and dried over Na2SO4, followed by evaporation. The product was further purified via TLC on silica gel GF (2000 mic) using benzene as the eluant.

Yield = 1.87 g (70 %). Cl,HllNO m/z- 245 (m*) IR (KBr): 3304, 1559, 1368, 980, 742 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 7.48 (dd, lH, J=8.0, 1.5 Hz), 7.58 (t, lH, J=8.0 Hz), 7.69 (dd, lH, J=8.0, 1.0 Hz), 7.76 (dd, lH, J=8.0, 1.0 Hz), 8.01 (d, lH, J=8.0 Hz), 8.12 (d, lH, J=8.0 Hz), 8.24 (d, lH, J=8.0 Hz), 8.37 (d, lH, J=8.0 Hz), 8.38 (d, lH, J=8.0 Hz), 9.34 (d, lH, J=8.0 Hz), 12.48 (s, lH, =N-OH).

The following compounds were similarly prepared from the appropriate starting materials:

3-Bromo-7-hydroxyimino-benz(de)anthracene. Recrystallized from toluene with charcoal.

Yield = 2.1 g (65%). Cl7Hl0BrNO m/z- 325 (m++1) IR (KBr): 3380, 1559, 1334, 1052, 947, 743 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.49 (dt, lH, J=8.0, 1.0 Hz), 7.57 (dt, lH, J=8.0, 1.0 Hz), 7.89 (t, lH, J=8.0 Hz), 8.05 (d, lH, J=8.0 Hz), 8.22 (dd, lH, J=8.0, 1.0 Hz), 8.34 (d, lH, J=8.0 Hz), 8.36 (dd, lH, J=8.0, 1,0 Hz), 9.40 (d, lH, J=8.0 Hz), 14.28 (s, lH, =N-OH).

3-Carboxamido-7-hydroxyimino-benz(de)anthracene.

Purification was achieved via TLC on silica gel GF (2000 mic) using hexane/ethyl acetate (1:1) as the eluant.

Yield = 1.91 g (70%).C18H11NO2 m/z- 273 (m+) IR (KBr): 2953, 1559, 1374, 931, 763 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 6.23 (s, 2H), 6.80 (dd, lH, J=8.0, 1.5 Hz), 7.24 (t, 1H, J=8.0 Hz), 7.41 (dt, lH, J=8.0, 1.5 Hz), 7.57 (t, lH, J=8.0 Hz), 8.07-8.18 (m, 3H), 8.90 (d, lH, J=8.0 Hz), 9.25 (dd, lH, J=8.0, 1.0 Hz), 12.07 (s, 1H, =N-OH).

EXAMPLE 39 <BR> <BR> <BR> <BR> <BR> <BR> <BR> <BR> l-[2,7-Dioxo-2,7-dihydro-3H-naphtho(1,2,3-de)quinolin-1-yl] pyridinium chloride N-(9,10-Dioxoanthryl)-2-N-chloroethanamide was produced by adding chloroacetyl chloride (5 g, 4.46 mmol) to 1-aminoantraquinone (5 g, 2.25 mmol) in dry benzene (100 ml), and heating the reaction mixture at 900C for 1.5 hours.

After cooling to 100C the precipitate was collected by filtration, washed with benzene, anhydrous ether, recrystallized from nitromethane, and dried.

Yield = 6.23 g (95 %). Cl6HloClNO3 m/z - 299 (m+)

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 4.59 (s, 2H, -CH2-C1), 7.92-8.03 (m, 4H), 8.19 (dd, lH, J=8.0, 1.0 Hz), 8.26 (dd, lH, J=8.0, 1.0 Hz), 9.03 (dd, lH, J=8.0, 1.0 Hz).

A suspension of the N-(9,10-dioxoanthryl)-2-chloroethanamide (2.5 g, 0.84 mmol) in dry pyridine (50 ml) was stirred at 1200C for 1 hour. After cooling to OOC, the precipitate was collected by filtration, washed with benzene and ether, recrystallized from water, and dried, yielding 1-[2,7-Dioxo-2,7-dihydro-3H-naphtho(1,2,3-de)quinolin-1-yl] pyridinium chloride.

Yield = 2.83 g (93.7%). C21H13C1N2O2 m/z- 325 (m+-35) IR (KBr): 3412, 3012, 1662, 1621, 1593, 1469, 1336, 1280, 700 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 6.31 (d, lH, J=8.0 Hz), 7.53 (dd, 1H, J=8.0, 1.0 Hz), 7.58 (dd, lH, J=8.0, 1.0 Hz), 7.79 (t, lH, J=8.0 Hz), 7.91 (dd, lH, J=8.0, 1.0 Hz), 8.00 (t, lH, J=8.0 Hz), 8.24 (dd, lH, J=8.0, 1.0 Hz),8.40 (dd, lH, J=8.0, 1.0 Hz), 8.48 (d, lH, J=8.0 Hz), 8.55 (d, lH, J=8.0 Hz), 9.04 (t, lH, J=8.0 Hz), 9.39 (d, lH, J=8.0 Hz).

1-[Bromo-5-methyl-2,7-dioxo-2,7-dihydro-3H-naphtho(1,2,3- de) quinolin-1-yl]pyridinium chloride was prepared in a similar manner using recrystallized from water from 3-bromo-6(2-pyridylamido)-benz(de)anthracene-7-one.

Yield = 0.83g (86%) . C22H14BrClN2O2 m/z- 418 (m+-35) IR (KBr): 3508, 3037, 1683, 1646, 1463, 1244, 1070, 707, 628 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): S (ppm) 2.66 (s, 3H, CH3), 6.40 (d, lH, J=8.0, Hz), 7.50 (dt, lH, J=8.0, 1.0 Hz), 7.74 (t, 1H, J=8.0 Hz), 8.14 (s, 1H, N-H), 8.25 (dd, 1H, J=8.0, 1.0 Hz),8.51 (t, lH, J=8.0 Hz), 9.01 (t, 1H, J=8.0 Hz), 9.40 (d, 1H, J=8.0 Hz).

1-[3-Methyl-3H-2,7-dioxo-2,7-dihydronaphtho(1,2,3-de)] pyridinium chloride have been prepared in a similar manner from N- (9, 10-dioxoanthryl) -2-chloro-N-methylethanamide, and recrystallized from water.

Yield = 3.12g (83 %). C22H15ClN2O2 m/z- 339 (m+-35) 1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 3.90 (s, 3H, N-CH3), 6.32 (d, 1H, J=8.0, Hz), 7.55 (dt, 1H, J=8.0, 1.0 Hz), 7.78 (dt, 1H, J=8.0, 1.0 Hz), 8.13 (t, lH, J=8.0 Hz), 8.22 (d, lH, J=8.0 Hz), 8.32 (dd, lH, J=8.0, 1.0 Hz), 8.40 (dd, lH, J=8.0, 1.0 Hz), 8.52 (d, lH, J=8.0 Hz), 8.55 (d, lH, J=8.0 Hz), 9.04 (t, lH, J=8.0 Hz), 9.38 (d, lH, J=8.0 Hz), 9.40 (d, lH, J=8.0 Hz).

EXAMPLE 40 1-(4-Methylpiperazin-l-yl)-3-methyl-3H-naphtho(1,2,3-de) quinoline-2,7-dione A suspension of N-(9,10-dioxoanthryl)-2-chloro-N- methylethanamide (0.78 g, 0.25 mmol) in l-methylpiperazine (10 ml) was stirred at 1250C for 2 hours. After cooling to OOC, the precipitate was collected by filtration, washed with benzene and ether, recrystallized from nitromethane, and dried.

Yield = 0.32 g (36%). C22H21N302 m/z- 359 (m+) 1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 3.90 (s, 3H, N-CH3), 6.32 (d, 1H, J=8.0 Hz), 7.55 (dt, lH, J=8.0, 1.0 Hz), 7.78 (dt, lH, J=8.0, 1.0 Hz), 8.13 (t, lH, J=8.0 Hz), 8.22 (dd, lH, J=8.0, 1.0 Hz), 8.32 (dd, lH, J=8.0, 1.0 Hz), 8.40 (dd, lH, J=8.0, 1.0 Hz), 8.52 (d, lH, J=8.0 Hz), 8.55 (d, lH, J=8.0 Hz), 9.04 (t, lH, J=8.0 Hz), 9.38 (d, lH, J=8.0 Hz), 9.40 (d, lH, J=8.0 Hz).

Conversion to the hydrochloride yielded 1-[(4-methylpiperazin-1-yl)]-3-methyl-3H-naphtho(1,2,3-de) quinoline-2 ,7-dione hydrochloride. C22H22ClN3O2

IR (KBr): 2826, 1675, 1656, 1559, 1315, 1132, 976, 812, 713 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 1.86-2.01 (m, 6H), 2.58 (d, lH, J=8.0 Hz), 2.80 (d, lH, J=8.0 Hz), 3.15 (s, 6H, N-CH3), 7.84 (dd, 1H, J=8.0, 1.0 Hz), 7.90-7.93 (m, 3H), 8.18 (dd, 1H, J=8.0, 1.0 Hz), 8.21 (dd, lH, J=8.0, 1.0 Hz), 8.28 (dd, 1H, J=8.0, 1.0 Hz).

EXAMPLE 41 3H-Naphtho (1,2,3 -de ) quinoline-2,7-dione A suspension of 1-[2,7-dioxo-2,7-dihydro-3H-naphtho(1,2,3-de) quinolin-1-yl]-pyridinium chloride (0.5 g, 0.14 mmol) in N,N-dimethylaniline was stirred at 2200C for 16 hours. After cooling, the precipitate was collected by filtration, washed with 2-propanol and ether, recrystallized from N,N-dimethylformamide with charcoal, and dried.

Yield = 0.11 g (32.3%). C16H9NO2 m/z- 247 (m+) IR (KBr): 3051, 2847, 1660, 1565, 1379, 1244, 779 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.72 (dd, lH, J=8.0, 1.0 Hz), 7.75 (s, lH, N-H), 7.79 (dd, 1H, J=8.0, 1.0 Hz), 7.84 (s, 1H), 7.92-7.85 (m, 2H0, 8.06 (dd, lH, J=8.0, 1.0 Hz), 8.32 (d, lH, J=8.0 Hz), 8.60 (d, lH, J=8.0 Hz). mp > 340°C <BR> <BR> <BR> <BR> <BR> 6-Bromo-4-methyl-3H-naphtho (1,2,3-de) quinoline-2,7-dione was prepared similarly from 1-[6-bromo-5-methyl-2,7-dioxo- 2,7-dihydro-3H-naphtho(1,2,3-de)]pyridinium chloride, and recrystallized from N,N-dimethylformamide with charcoal.

Yield = 0.27 g (79 %). Cl,Hl0BrNO2 m/z- 340 (m+) IR (KBr): 3032, 1683, 1647, 1558, 1282, 755 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 2.57 (s, 3H, CH3), 6.64 (m, 1H), 7.12 (t, lH, J=8.0 Hz), 7.52 (s, 1H), 7.68-7.85 (m, 2H), 8.54 (d, 1H, J=8.0 Hz), 11.40 (s, 1H, N-H).

EXAMPLE 42 3-Methyl-3H-naphtho(1,2,3-de)quinoline-2,7-dione 3H-Naphtho(1,2,3-de)quinoline-2,7-dione (0.49 g, 0.2 mmol) was heated with excess of dimethyl sulfate (10 ml) at 1450C for 2 hours. After cooling, the reaction mixture was diluted with benzene (50 ml), and the precipitate was collected by filtration, washed with benzene, boiled in 2-propanol and filtered off after cooling, recrystallized from 2-propanol with charcoal, and dried.

Yield = 0.31 g (59.6%). Cl7HllNO2 m/z - 261 (m+) EXAMPLE 43 2-Chloro-naphtho(1,2,3-de)quinoline-7-one A suspension of 3H-naphtho(1,2,3-de)quinoline-2,7-dione (1.0 g, 0.4 mmol) in phosphorus oxychloride (15 ml) was heated at 105°C for 5 hours. After cooling, the dark reaction mixture was poured into ice (100 g), and the precipitate, was filtered off, washed with hot water (150 ml), recrystallized from m-xylene, and dried.

Yield = 0.93 g (87.7%). Cl6H8ClNO m/z - 265 (m+) EXAMPLE 44 1-Amino-3H-naphtho(1,2,3-de)quinoline-2,7-dione A suspension of 1-[2,7-dioxo-2,7-dihydro-3H-naphtho (1,2,3-de)quino]in-1-yl]pyridinium chloride (3.61 g, 1.0 mmol) in aniline (17 ml) was heated at 1900C for 5 minutes to 1.5 hours. After cooling, methanol (40 ml) was added, and the precipitate was collected by filtration, washed with methanol, recrystallized from N,N-dimethylformamide with charcoal, and dried.

Yield = 2.41 g (92%). C16H10N2O2 m/z- 262 (m+)

IR (KBr): 3320, 2881, 1674, 1637, 1546, 1349, 758 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.25 (s, 2H, NH2), 7.52 (d, 1H, J=8.0 Hz), 7.55 (d, lH, J=8.0 Hz), 7.60 (t, lH, J=8.0 Hz), 7.64 (s, lH, N-H), 7.85 (dt, lH, J=8.0, 1.0 Hz), 8.11 (dd, 1H, J=8.0, 1.0 Hz), 8.41 (dd, lH, J=8.0, 1.0 Hz), 8.62 (d, 1H, J=8.0 Hz). mp >3500C Analysis: Calcd. for C16H10N2O2: C, 73.27; H, 3.84; N, 10.68 %.

Found: C, 73.05; H, 3.87; N, 10.69 %. <BR> <BR> <BR> <BR> <BR> <BR> <BR> l-Amino-3-methyl-3H-naphtho (1,2,3-de) quinoline-2,7-dione was similarly prepared from 1-[3-methyl-3H-2 ,7-dioxo- 2,7-dihydro-naphtho(1,2,3-de)]pyridinium chloride, and recrystallized from N,N-dimethylformamide with charcoal.

Yield = 0.27 g (39%). C17H12N2O2 m/z- 276 (m+) IR (KBr): 3322, 1653, 1648, 1593, 1337, 985, 759 cm-1.

1H NMR (300 MHz, DMSO-d6, TMS): 6 (ppm) 3.84 (s, 3H, N-CH3), 7.33 (s, 2H, -NH2), 7.57 (dd, lH, J=8.0, 1.0 Hz), 7.61 (dd, lH, J=8.0, 1.0 Hz), 7.83 (dd, lH, J=8.0, 1.0 Hz), 7.87 (dd, lH, J=8.0, 1.0 Hz), 8.19 (dd, lH, J=8.0, 1.0 Hz), 8.39 (dd, lH, J=8.0, 1.0 Hz), 8.62 (d, lH, J=8.0 Hz). mp 259°C.

Analysis: Calcd. for C17H12N2O2 x 0.1 H2O: C, 73.42; H, 4.35; N, 10.07 %. Found; C, 73.33; H, 4.41; N,9.98 %.

1-Amino-6-bromo-4-methyl-3H-naphtho(1,2,3-de)quinolin-2,7 - dione was similarly prepared from 1-[6-bromo-5-methyl-2,7- dioxo-2,7-dihydro-3H-naphtho(1,2,3-de)pyridinium chloride, and recrystallized from N,N-dimethylformamide with charcoal.

Yield = 0.31 g (87%). C17H11BrN2O2 m/z- 356 (m+1) IR (KBr): 3434, 3334, 3170, 1670, 1646, 1584, 1335, 1038, 625 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): S (ppm) 2.55 (s, 3H, -CH3), 7.29 (s, 2H, -NH2), 7.55 (d, lH, J=8.0 Hz), 7.60 (d, lH,

J=8.0 Hz), 7.79 (dt, lH, J=8.0, 1.0 Hz), 8.23 (dd, lH, J=8.0, 1.0 Hz), 8.55 (d, lH, J=8.0 Hz).

Example 45 2,7-Dioxo-4-methyl-1-trimethylamino-3-H-naphtho(1,2,3-de) quinolinium 4-methylbenzosulfonoate A mixture of 1-amino-3-methyl-3H-naphtho (1,2, 3-de) quinoline-2,7-dione (0.276 g, 0.1 mmol) and methyl p-tolyenesulfonate (3.0 g, 1.6 mmol) was heated at 1350C for 1.5 hours. After cooling, dry ether (150 ml) was added, and the precipitate was collected by filtration, washed with dry ether, recrystallized from 2-propanol, and dried.

Yield = 0.27 g (55%). C27H26N2OsS m/z- 319 (m+-171) IR (KBr): 3502, 2987, 1683, 1668, 1559, 1320, 1202, 1050, 804, 693, 569 cm-l.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 2.27 (s, 3H, C6H4-CH3), 3.94 (s, 3H, N-CH3), 4.97 (s, 9H, N-CH2)3), 7.09 (d, lH, J=8.0 Hz), 7.44 (d, 1H, J=8.0 Hz), 8.14 (t, 1H, J=8.0 Hz), 8.24 (d, lH, J=8.0 Hz), 8.36 (d, lH, J=8.0 Hz), 8.52 (t, lH, J=8.0 Hz), 9.02 (d, lH, J=8.0 Hz), 9.18 (d, lH, J=8.0 Hz), 10.51 (d, lH, J=8.0 Hz).

EXAMPLE 46 l-Acetamido-3H-naphtho(1,2,3-de)quinoline-2,7-dione 2-Methyl-naphtho(1,2,3-de)oxazole[5,4-bzquinolin-8-one was produced from a suspension of 1-amino-3H-naphtho(1,2,3-de) quinoline-2,7-dione (0.13 g, 0.05 mmol) in acetic anhydride (2 ml). The suspension was ref fluxed for 2 hours, cooled and precipitate was collected by filtration, washed with 2-propanol and ether, and recrystallized from glacial acetic acid and N,N-dimethylformamide with charcoal.

Yield = 0.091 g (6 3%). C18H10N2O2 IR (KBr): 1674, 1648, 1581, 1297, 737 cm1.

1H NMR (300 MHz, CF3CO2D, TMS): s (ppm) 3.04 (s, 3H, -CH3) 8.01 (t, lH, J=8.0 Hz), 8.13 (t, lH, J=8.0 Hz), 8.39 (t, lH, J=8.0 Hz), 8.66 (d, lH, J=6.5 Hz), 8.67 (d, lH, J=8.0 Hz), 9.07 (d, lH, J=8.0 Hz), 10.00 (d, lH, J=8.0 Hz).

The 2-Methyl-naphtho(1,2,3-de)oxazole[5,4-b]quinolin-8-one product (0.14 g, 0.05 mmol) was dissolved with ref fluxing in aqueous 1.4-dioxane (1:1) (30 ml), and hydrochloric acid (35 %) (1.0 ml) was added. The reaction mixture was cooled, and neutralized with a solution of sodium bicarbonate. The precipitate was removed by filtration, washed with 2-propanol, recrystallized from a mixture of acetic acid and water (1:1) with charcoal, and dried, yielding 1-Acetamido-3H-naphtho(1,2,3-de)quinoline-2,7-dione.

Yield = 0.08 g (53%). C1iH12N2O3 IR (KBr): 3294, 2825, 1690, 1653, 1558, 1478, 1244, 926, 764 cm~l.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 2.16 (s, 3H, CH3), 7.65-7.82 (m, 5H), 8.10 (d, lH, J=8.0 Hz), 8.29 (d, lH, J=8.0 Hz), 10.14 (s, 1H).

EXAMPLE 47 1-Benzamide-3H-naphtho(1,2,3 -de) quinoline-2,7-dione 2-Phenyl-naphtho(l,2,3-de)oxazole[5,4-b]quinolin-8-one was prepared from a suspension of l-amino-3H-naphtho(l,2,3-de) quinoline-2,7-dione (0.262 g, 0.1 mmol) in the benzoyl chloride (15 ml) by heating the suspension at 1100C for 1 hour. After cooling the precipitate was filtered and washed with 2-propanol and ether, and recrystallized from N, N-dimethylformamide with charcoal.

Yield = 0.27 g (78 %). C22H12N2O2 IR (KBr): 1660, 1544, 1267, 1025, 699 cm~l. lH NMR (300 MHz, CF3CO2D, TMS): 6 (ppm) 7.74 (d, lH, J=6.0 Hz), 7.78 (d, 1H, J=6.0 Hz), 7.87 (t, lH, J=8.0 Hz), 8.03 (t, lH, J=8.0 Hz), 8.19 (t, lH, J=8.0 Hz), 8.39 (t, lH, J=8.0 Hz), 8.53 (d, lH, J=6.5 Hz), 8.55 (d, lH, J=6.5 Hz),

8.68 (d, lH, J=6.5 Hz), 8.71 (d, lH, J=6.5 Hz), 9.10 (dd, lH, J=6.5, 1.0 Hz), 10.15 (t, 1H, J=8.0 Hz).

The 2-Phenyl-naphtho(1,2,3-de)oxazole[5,4-b]quinolin-8-one product (0.17 g, 0.05 mmol) was dissolved with ref fluxing in aqueous 1.4-dioxane (1:1) (30 ml), and sodium hydroxide solution (40%) (0.5 ml) was added to the solution. The mixture was cooled, neutralized with sulfuric acid and filtered. The solid was washed with water and 2-propanol, recrystallized from mixture acetic acid/water (3:1), and dried, yielding l-Benzamide-3H-naphtho(1,2,3-de) quinoline-2,7-dione.

Yield = 0.11 g (60%). C23H14N2O3 IR (KBr): 3504, 3327, 2828, 1689, 1649, 1558, 1263, 926, 785 cm1.

1H NMR (300 MHz, DMSO-d6, TMS): s (ppm) 7.57-7.84 (m, 6H), 7.82 (t, lH, J=8.0 Hz), 8.08 (d, 1H, J=8.0 Hz), 8.14 (d, lH, J=8.0 Hz), 8.34 (d, lH, J=8.0 Hz), 8.72 (d, lH, J=8.0 Hz), 10.29 (s, 1H).

The molecular binding and antiviral activity of the benzanthrone class of molecules and a benzanthrone series structure activity relationship chart are provided in the tables below.

Molecular Binding and Antiviral Activity of the Benzanthrone Class of Molecules R1 R2 R3 R4 Salt Molecular RSV PRA HEp2 XTT Screening BrX HX HX HX 0.0045 1.57 38.4 HX HX HX HX 1.28 65.7 HX HX HX HX 0.02 IX HX HX HX 0.0035 0.64 31.98 IX HX HX HX IX HX HX HX CNX HX HX HX 0.007 0.38 6.8 CNX HX HX HX 0.4 1.32 5.32 CH02X HX HX HX 0.45 3.62 CH02X HX HX HX 0.2 CO2X HX HX HX Sodium 2.78 5.67 CO2X HX HX HX Sodium 3.5 4.3 11.8 C6H11N20X HX HX HX 1.16 23.65 C6H11N20X HX HX HX 0.8 CH1ONOX HX HX HX 999 3.37 37.51 C5H8N02X HX HX HX 1.49 18.5 CH2NOX HX HX HX 0.51 24.89 CH2NOX HX HX HX 0.23 C10H12NO2X HX HX HX 0.07 1.36 39.59 C5H10NOX HX HX HX 1.47 12.24 C2H3O2X HX HX HX 0.04 0.17 10.77

R1 R2 R3 R4 Salt Molecular RSV PRA HEp2 XTT Screening C6H10NOX HX HX HX 0.1 1.55 32 C5H8N03X HX HX HX 7.3 49.5 C2H4NOX HX HX HX 0.44 11.26 C7H10N3OX HX HX HX 3.64 C5H903X HX HX HX 0.92 5. C5H8N03X HX HX HX 0.9 14. C9H1ONOX HX HX HX 999 1.81 15.55 C9H12N03X HX HX HX 0.17 0.95 6.41 C6H5N20X HX HX HX 0.04 1. 16.72 C6H5N20X HX HX HX C8H9N2OX HX HX HX 0.79 5.63 C3H5N203X HX HX HX 3.41 39.34 C2H4N02X HX HX HX 0.72 11.6E C3H4N03X HX HX HX 1.3 10.58 15.87 C5H6N05X HX HX HX 22.55 8.1 C12H11N203X HX HX HX 7.76 25 C7H13NO3X HX HX HX 2.47 31.5 C7H13N403X HX HX HX 2.1 9.7 C7H12N03X HX HX HX C7H12NO3X HX HX HX 1.14 17 C6H8N03X HX HX HX 2.24 33. C6H8N03X HX HX HX 2. 16. C2HN40X HX HX HX 0.41 7. C2H4NO3SX HX HX HX 4.54 7.9 BrX BrX HX HX 18.5 43.1 CNX CNX HX HX 999 5.5 HX O3SX HX HX 4.37 8.5 HX C3H3NX2 HX HX 1.99 11.6 BrX O3SX HX HX 0.56 31.6 CH02X CH02X HX HX 70.71 8.1

R, R2 R3 R4 Salt Molecular RSV PRA HEp2 XTT Screening CO2X CO2X HX HX 34.96 12.7 HX C3H4NX2 HX HX 18.92 3 CH2NOX CH2NOX HX HX 17 0.0 6.1 CH2NOX BrX HX HX 999 0.0 4.1 CNX BrX HX HX 99 0.24 7.2 C6H11N2OX C6H11N2OX HX HX 22 0.05 4.25 CH02X BrX HX HX 1 6 0.3 2 CO2X BrX HX HX 1 6 0.6 10.1 CH30X HX HX HX 0. 9.9 CH30X HX HX HX CH30X HX HX HX CH4NX HX HX HX C8H8NO3SX HX HX HX 16 10 6.8 C5H4NO5X HX HX HX K+ 4.42 12.9 C6H8N05X HX HX HX 12. | 16. C7H3BrOX2 BrX HX HX C8H16N4O3X HX HX HX 7. 3. @ 9. C5H8NO3X HX HX HX 999 29 19.9 C13H13N2O3X HX HX HX 0.1 3.9 z 35.6 C6H10N04X HX HX HX 0.31 17.7 23.1 C14H18NO3X HX HX HX 0.018 25.3 19.8 C8H14N03X HX HX HX 0. 0.75 7. C12H14N04X HX HX HX 0.1 z 22.9 52.8 C6H6N05X HX HX HX sodium salt 1 0.81 15.8 C7H11N2O3X HX HX HX 0.57 6.8 17.1 C8H14NO3SX HX HX HX 1. 16.2 34. C6H8N204X HX HX HX sodium salt 3.6 3.1 17.3 C2H40X HX HX HX C2H4N03SX C2H4N03SX HX HX 1 0.45 9.8 CHN4X CHN4X HX HX 5 9.7 20.6

R1 R2 R3 R4 Salt Molecular RSV PRA HEp2 XTT Screening BrX C3H3NX2 HX HX 0.4 0.21 5.6 CH2CIX HX HX HX 0.01 6 0.79 2.1 C6H13N2X HX HX HX HCI 0.17 1.2 2.1 C6H13N2X HX HX HX HCI 0.5 CH20X BrX HX HX 0.14 CH30X CH30X HX HX 0.9 C6H13N2X HX HX HX 0. CH20X HX HX HX C2H4NOX HX N02X HX C2H4NOX HX HX HX H2NX HX H2NX HX H2NX HX N02X HX C2H5OX HX HX HX C2H5OX HX HX HX C9H18NO2X HX HX HX BrX HX HX C5H5N2X C5H13NO3PX HX HX HX CH3X HX HX HX C3H502X HX HX HX

Ia%-rm Series SAR R3 R3 R1 R7 'D uj Al RI R2 R3 « q o o n o t C Br x115 0.0045 1.57 38.4 v, 0 C t es o o ct N 1D F X A xl 0 C N x15 0.007 0.38 6.8 0 C N x5 Xs 0.4 1.32 5.32 o tj xl5 0.2 0.45 3.62 X1 OH C 0 x5 Na+ 3.5 4.3 11.8 u, [ t9 \n ZN

IV! $ Series SAR R3 R3 ,R1 R7 (I, X N rv ~ t N ~ LU o o; R2 t e X t a C x5 0.8 1.16 23.65 0 z O Ci n! q o x15 999 3.37 37.52 F C x115 0.3 1.49 18.5 0 v, 0 Y PZ: II Xu7=o X-=O X--O 10.77 ~ g att

Benzanthrone Series SAR R3 R3 1R1 I I u, 'L O x = 6"4 Al RI R2 R3 O N » 8 v O e O O ~ ~ U) CM F eD U) m ~ ~ to ~ Cy ox115 1.2 0.44 11.26 con ¼ 0 C x15 0.28 0.92 5.5 0 C x115 0.55 0.96 14.7 NOH 0 C x5 999 1.61 15.55 x-=o x-=o x-=o x-=o x-=o x-=o x--o X nz .@, X a: C 4 U > < X X X

I Series SAR R3 R3 r\r (3 CO CO cd "4 5"4 Al RI R2 R3 t CM e a cu m v ~ (cnn <s - co In 0 C x115 1 0.79 5.63 C x5 999 3.41 39.34 C x15 2.5 0.72 11.68 x,)¼NocH3 - t C x115 8 22.55 8.1 ¼ 0 'CA a: E =t tW f

Benzanthrone Series SAR R3 "4½;{lRlR7 LD LO V) 00 a, nr r cd rc: ri Al RI R2 N ~ O t . C y%Iffi\ 0x15 3.5 7.76 25 Z tn o o o ~ o C x5 0.95 1.14 17 C vK x15 0.3 2.9 16.5 ½ C X,NIN xIs 0.14 0.41 7.8 re C Ofl 0x15 10 4.54 7.9 X, 3 C U7 UZ U) UX 0.1 18.5 43.1 xl m @ XX XX X X

Benzanthrone Series SAR R3 V) rC) U) (D r Ic O uj cd r: ad (j Al o; R2 o r o c re C 0 x5 999 4.37 8.5 0 C x5 0.065 1.99 11.6 w C Br oO\\s Xd x15 0.09 0.56 31.6 xX rye Xi OH ½ oIl C 0 0 X4 x5 999 34.96 12.7 x¼o. ½ C N X x115 0.04 18.92 3 X O X=O X=O X=O X=O X=O X= O a xX O ùS° /X) *\=00 0SO oF * @ 1C <

m u, cu SAR R3 R3 fRI R7 "4 5"4 Al o R2 o N o o = o C 0 X4 x115 17 0.04 6.15 z o, a, o: ~ no X X In Br N x4 x15 999 0.24 7.2 xK Br'/ 0 C x15 22 0.05 4.25 mi C x1;¼OH Br x15 16 0.39 24 0 C 0 x4 x5 16 0.6 10.14 x1o- Br C x115 0.08 0.4 9.9 Xi OH o z O m m m m

Benzanthrone cn SAR R3 R4¼;?)IRIR7 Al RI R2 t N N N R7 Salt TiO45PNB RSVPRA HEp2xTT C Xi NH2 Z lD N O Q C ox115 2.7 4.42 12.9 C x5 0.08 12.7 16.3 x½o C Br ~ ~ =X=X- ~ ~ I 0 C X-=O X=O X--O 999 X--O 19.9 =-r TA 'ZD

cr, r: aq m oq oq r: N u) X O cu Ln 'Vn w I Al RI CX s U) s CSj eo LL lr o e o o eo ~ o C X15 0.018 25.3 19.8 F C x15 ~X~ ~ Z ~ C yy. xIIs 0.13 22.9 52.8 C ..: ox115 Na+ I 0.81 15.8 C .t0ty ul ux u: 6.8 17.1 X=O X=O X=O X=O X=O X=O X=O Ut o cn a: g <4 °X\X m < t, O O O O O O

Benzanthrone Series 00 (0 SAR R3 cu ;g cd ri 'cr R6 1<? C xI15 1.7 16.2 34.3 C x115 Na+ 3.6 3.1 17.3 c xtNA II 0 C N 115 16 0.45 9.8 xi)¼s/ro 0 C NN\\ N x4 11S 5 9.7 20.6 a xiN p: w C x115 0.016 0.79 2.1 x=o Cl S eAX m < O O O O O O O

x Series SAR R3 R3 fRI IR7 "4 5R6 Al RI |N R6 R7 Salt TIO45PNB X HEp2XTT C a! x5 HCI 0.17 1.2 2.1 m o ~ Xi OH 0 xl C x5 0.3 o11 C 0-OH3 x5 0.034 C H3 O\\ O x115 0.6 X10NxI2 C H3 x15 0.45 x=o x=o x--o x-=o x-=o x-=o x-=o z xs m tV WaX f

X Series SAR R3 n Al RI R2 R3 R4 R5 R6 R7 Salt TIO45PNB RSVPRA HEp2xTT - - -=-- - -= xl }2 C o, a, x115 0.9 xl NI 'o 0 Xl C XO-CH x5 0.018 C x.oC) x15 0.01 A R1 H3c OH C C Br x5 tY x o x=o x=o x=o / x=UN o 1 < ' f

Benzanthrone Series SAR R3 1'4D;?)IRIR7 Al RI R2 R3 R4 R5 R6 R7 Salt TI045PNB RSVPRA HEp2xTT 8 Br N O N 42.31 x1 0 C x115 0.13 2.88 16.41 ¼ C o x15 0.06 0.53 19.56 xl C 0x115 0.1 0.72 9.9 crr lZ C Br x1 X=O X O X=O xr=O == k X tS m <: O O O O O O O

Benzanthrone Series SAR R3 R3 ,R1 W- ur s "4 Re a RI R2 ~ o o 0% X1 OH Na+ Xi 0 C OH 0MM Xi OH NH2 "S t XI 0 OH N 011 x115 100 0.g7 5.6 x2 0 N oil A=zos 999 x-~o 4 m ~ C«OD a: ~ X -o=x o=x t r f X ° t X m <: O O O O O z z

pz OD SAR R3 R3 io cu In Al RI R2 R3 oq q N 1 t N xI15 0.05 39.56 35.7 X O sOo O 0-sa N 0x1I2 a, 0x115 80 49.11 39.8 N 0 H2N x115 999 0.076667 2.65 X3 0 x2 N Ox115 () 68.985 Å N 0 XIs 4.6 15.2 19.1 II 0 N oil I xI15 Cl(-) 17.86 53.4 x2 ~X 0 salt >iP-- N' 0 1 x2 "S Br 1« r < X e « H o=x o=x a o=x o=x o=x g <Z Z lzX

Benzanthrone Series SAR R3 R3 coS co (o cs N t O ~ U) tt CC cn 5R6 Al RI R2 N s N CM N 0 0 x115 cn 98.41 43.5 0 X7 X2 H3C X3 Br Br ~ Z° ~~ O-gs~ CO 0 x2 N CI x5 100 3.5 11.8 x2 0 N I xI15 x6 CH3 HO 1.1 21.9 51.6 X2 Br N \ H2NN x115 CH3 1.7 45.5 43.1 x3 o I x7 x2 Br N 011 x115 xsn 100 X £ co x2 Br N xiMOH3 {i x15 HO 8 2 9.5 X-=O X-=O X--O X-=O X-=O X-=O X-=O x2 a: o = x o = x cJ x O = x O = x o = x O = x m < z z z z z z z

Benzanthrone Series SAR R3 t ~ o , ç cO N r C) (D P V) Al RI R2 R3 X N n ~ P N CH3 011 cHa x115 Benzyl 0.033 1.8 10 xl CO 8 N oil H2N X5 2.7 10 CH3 x3 0 ~ F N CH3 xI15 999 13.8 45.3 xl I M 0 x2 N m m HO 999 18.4 61.4 re X2 Xi N CH3 H2N xIIs HOl 0.18 2.8 4.6 xl x3 0 <t . "|iS 3.3 13.4 x2 N x"=o x"=o x"=o 999 18 32.5 x .@ e \ x 9 3 I o = xN o =xN o =xN o = x t o =xN o = x @ ~ 5: X r O I r r I N ~ x x x x x x x m < z z z z z z z While it is apparent that the invention disclosed herein is well calculated to fulfill the objects stated above, it will be appreciated that numerous modifications and embodiments may be devised by those skilled in the art.

Therefore, it is intended that the appended claims cover all such modifications and embodiments that fall within the true spirit and scope of the present invention.