*Storage: {[sel_prStorage]}
*Shipping: {[sel_prShipping]}
The BI-3802 was designed by Boehringer Ingelheim and could be obtained free of charge through the Boehringer Ingelheim open innovation portal opnMe.com, associated with its negative control.
9,10-Phenanthrenedione is a quinone compound with fluorescent properties, acting as a TRPA1 agonist.
4.5
*For Research Use Only !
Change View
Size | Price | VIP Price | US Stock |
Global Stock |
In Stock | ||
{[ item.pr_size ]} |
Inquiry
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.discount_usd) ]} {[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]} |
Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]} | Inquiry {[ item.pr_usastock ]} In Stock Inquiry - | {[ item.pr_chinastock ]} {[ item.pr_remark ]} In Stock 1-2 weeks - Inquiry - | Login | - + | Inquiry |
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days
1-2weeks
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd,1,item.mem_rate,item.pr_is_large_size_no_price, item.pr_usd) ]}
Inquiry
{[ getRatePrice(item.pr_usd,item.pr_rate,1,item.pr_is_large_size_no_price, item.vip_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
{[ getRatePrice(item.pr_usd, 1,1,item.pr_is_large_size_no_price, item.pr_usd) ]}
In Stock
- +
Please Login or Create an Account to: See VIP prices and availability
US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.
Synthesis of TU100 Analogs and Biological Assays
Oladapo, Feyisope Tonye ;
Abstract: TU-100 (14-methyl-5H-5,12-epiminobenzo[4,5]cyclohepta[1,2-b]naphthalene-6,11,13(12H)-trione) exhibits exceptional chemotherapeutic properties. It operates via a distinct mechanism that triggers cell death to create cytotoxic effects while concurrently inhibiting topoisomerase I and II. Its efficacy rivals that of well-known chemotherapeutic drugs like Daunorubicin. The distinctive characteristics of TU100 have led to initiatives aimed at creating structurally similar compounds to discover even more effective bioactive alternatives. The analog synthesis incorporated quinoxaline or its derivatives (diphenyl quinoxaline, dipyridinyl quinoxaline, and dibenzophenazine-10,13-dione) that have been shown to have promising chemotherapeutic effects. Synthesizing the hetero naphthoquinones required a multistep synthetic process, so quinoxaline/ derivatives intermediates are first prepared, then the intermediates are reacted with 4-hydroxy-N-methylisoquinolinum iodide to yield the TU100 analogs. The TU100 analogs were analyzed for their cytotoxic effect compared to that of TU100. All the analogs showed cytotoxic effects, with TU100 having a reduced cell viability compared to the analogs in BT5 cell line, while the analogs showed similar effects with TU100 in PC3 cell line, except for the Phenazine analog, which had greater cell viability compared to the others.
Show More >
Keywords: TU100 ; Quinoxaline analog ; Diphenyl Analog ; Pyridinyl analog ; Phenazine analog ; Cancer
Show More >
CAS No. : | 84-11-7 |
Formula : | C14H8O2 |
M.W : | 208.21 |
SMILES Code : | O=C1C(=O)C2=CC=CC=C2C2=CC=CC=C12 |
MDL No. : | MFCD00001163 |
InChI Key : | YYVYAPXYZVYDHN-UHFFFAOYSA-N |
Pubchem ID : | 6763 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319-H335 |
Precautionary Statements: | P261-P305+P351+P338 |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With potassium hydroxide; In ethanol; at 50℃; for 5h; | 1000mL, 3-neck round bottom flask, 2,7-dibromo-phenanthrene-9,10-dione 50 g (0.240 mol), 1,3- bis ((4-bromophenyl) propan-2 one was added 500ml of 80g of ethanol and stirred. In the potassium hydroxide (KOH) in 30g of this solution and stirred for 5 hours at 50 C. The resulting solid was filtered off after cooling the reaction solution to room temperature and washed well with methanol. Vacuum drying the solid obtained to give an intermediate A-1 70 g (yield 60%). |
60% | With potassium hydroxide; In ethanol; at 50℃; for 5h; | 50 g (0.240 mol) of 2,7-dibromophenanthrene-9,10-dione, 1,3-bis (4-boromophenyl) propa-2-one (1000 ml, in a three-neck round bottom flask) 80 g of 1,3-bis (4-bromophenyl) propan-2-one) and 500 ml of ethanol were added and stirred. Potassium hydroxide and 30 g of KOH were added to the solution and stirred at 50 C. for 5 hours. After cooling the reaction solution to room temperature, the resulting solid was filtered and washed well with methanol. The obtained solid was dried in vacuo to give 70 g (yield 60%) of the target compound A. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In methanol; acetic acid; at 70℃; for 2.0h; | 10.1 g (82 mmol) of <strong>[608-32-2]1,2,3-triaminobenzene</strong> and 4.6 g (70 mmol) of 9,10-phenanthrenequinone were placed in a four-necked flask, to which 350 g of a solvent of acetic acid and methanol at 1:1 was added for dissolution, followed by reaction at a reaction temperature of 70°C for 2 hours. After the reaction, the solvent was removed and the resulting product was washed with methanol to obtain the intended product. Yield: 17.1 g Ocher solid m/z: 295 (calculated: 295.11) 13C-NMR: 146.932, 144.145, 143.084, 139.740, 133.473, 133.007, 132.656, 132.213, 131.602, 131.488, 130.847, 130.473, 128.465, 126.869, 126.831, 126.663, 123.900, 116.243, 108.647 ppm |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With ammonium acetate; acetic acid; for 2h;Inert atmosphere; Reflux; | Synthesis of (2-(4-(9H-carbazol-9-yl)phenyl)-1-phenyl-1H-phenanthro[9,10-d]imidazole (M1): a mixture of <strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1.00 g, 3.70 mmol), phenanthrene-9,10-dione (767.50 mg, 3.70 mmol), aniline (0.85 g, 18.50 mmol), ammonium acetate (1.14 g, 14.80 mmol), and acetic acid (10 mL) were refluxed under nitrogen in an oil bath. After 2 h, the mixture was cooled and filtered. The solid product was washed with an acetic acid/water mixture (1:1, 150 mL) and water. It was then purified by chromatography using CH2Cl2/petroleum ether (1:1) as eluent to obtain the product as white powder. Yield: 75%. 1H NMR (500 MHz, DMSO, δ): 8.96 (d, J = 8.30 Hz, 1H), 8.91 (d, J = 8.45 Hz, 1H), 8.74 (d, J = 7.36 Hz, 1H), 8.26 (d, J = 7.83 Hz, 2H), 7.89 (d, J = 8.22 Hz, 2H), 7.84-7.76 (m, 6H), 7.73 (t, J = 7.50 Hz, 6.43 Hz, 1H), 7.66 (d, J = 7.94 Hz, 2H), 7.59 (t, J = 6.97 Hz, 7.68 Hz, 1H), 7.46 (t, J = 7.50 Hz, 7.14 Hz, 2H), 7.40 (d, J = 8.61 Hz, 2H), 7.38 (t, J = 7.68 Hz, 7.68 Hz, 1H), 7.32 (t, J = 7.68 Hz, 7.68 Hz, 2H), 7.11 (d, J = 8.47 Hz, 1H); 13C NMR (500 MHz, CDCl3, Hz): 140.53, 130.80, 130.40, 130.14, 129.15, 128.39, 127.42, 126.61, 126.39, 126.02, 124.19, 123.57, 123.18, 120.91, 120.35, 120.20, 109.78; FTIR (KBr, ν, cm-1) 3058, 1625, 1532, 1475, 1451, 1429, 1378, 1358, 1241, 1225, 1174, 1147, 1111, 1018, 1004, 929, 844, 750, 724, 667, 620, 563, 535; MALDI-TOF (m/z): [M+] calcd for C39H25N3: 535.64; Found: 535.90. Anal. calcd for C39H25N3: C 87.45, H 4.70, N 7.84; Found: C 87.45, H 4.66, N 8.03. |
75% | With ammonium acetate; acetic acid; at 120℃; for 2h;Inert atmosphere; | A mixture of<strong>[110677-45-7]4-(9H-carbazol-9-yl)benzaldehyde</strong> (1.00 g,3.70 mmol),phenanthrene-9,10-dione (767.50 mg,3.70 mmol), aniline(0.85 g,18.50 mmol), ammonium acetate (1.14 g,14.80 mmol), and acetic acid (10 mL) were refluxed undernitrogen in an oil bath. After 2 h, the mixture was cooledand filtered. The solid product was washed with an aceticacid/water mixture (1:1,150 mL) and water. It was thenpurified by chromatography using CH2Cl2/petroleum ether(1:1) as eluent to obtain the product as white powder.Yield: 75%. 1H NMR (500 MHz, DMSO, d): 8.96 (d, J =8.30 Hz, 1H), 8.91 (d, J = 8.45 Hz, 1H), 8.74 (d, J = 7.36 Hz,1H), 8.26 (d, J = 7.83 Hz, 2H), 7.89 (d, J = 8.22 Hz, 2H),7.84-7.76 (m,6H), 7.73 (t, J = 7.50 Hz, 6.43 Hz, 1H), 7.66(d, J = 7.94 Hz, 2H), 7.59 (t, J = 6.97 Hz, 7.68 Hz, 1H), 7.46(t, J = 7.50 Hz, 7.14 Hz, 2H), 7.40 (d, J = 8.61 Hz, 2H), 7.38(t, J = 7.68 Hz, 7.68 Hz, 1H), 7.32 (t, J = 7.68 Hz, 7.68 Hz,2H), 7.11 (d, J = 8.47 Hz, 1H); 13C NMR (500 MHz, CDCl3,Hz): 140.53, 130.80, 130.40, 130.14, 129.15, 128.39,127.42, 126.61, 126.39, 126.02, 124.19, 123.57, 123.18,120.91, 120.35, 120.20, 109.78; FTIR (KBr, m, cm1) 3058,1625, 1532, 1475, 1451, 1429, 1378, 1358, 1241, 1225,1174, 1147, 1111, 1018, 1004, 929, 844, 750, 724, 667,620, 563, 535; MALDI-TOF (m/z): [M+] calcd for C39H25N3:535.64; Found: 535.90. Anal. calcd for C39H25N3: C 87.45,H 4.70, N 7.84; Found: C 87.45, H 4.66, N 8.03. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With ammonium acetate; acetic acid; for 2h;Inert atmosphere; Reflux; | Synthesis of 1-phenyl-2-(9-phenyl-9H-carbazol-3-yl)-1H-phenanthro[9,10-d]imidazole (M3): a mixture of <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (500.00 mg, 1.85 mmol), phenanthrene-9,10-dione (460.50 mg, 2.21 mmol), aniline (0.50 g), ammonium acetate (0.60 g, 8.00 mmol), and acetic acid (10 mL) were refluxed under nitrogen in an oil bath. After 2 h, the mixture was cooled and filtered. The solid product was washed with an acetic acid/water mixture (1:1, 150 mL) and water. It was then purified by chromatography using CH2Cl2/petroleum ether (1:1) as eluent to obtain the product as white powder. Yield: 80%. 1H NMR (500 MHz, DMSO, δ): 8.96 (d, J = 7.98 Hz, 1H), 8.91 (d, J = 8.67 Hz, 1H), 8.76 (d, J = 7.28 Hz, 1H), 8.35 (s, 1H), 8.09 (d, J = 7.53 Hz, 1H), 7.81-7.76 (m, 4H), 7.73-7.68 (m, 6H), 7.64 (d, J = 7.08 Hz, 2H), 7.58 (t, J = 7.69 Hz, 7.08 Hz, 2H), 7.48 (t, J = 7.08 Hz, 7.00 Hz, 1H), 7.39-7.31 (m, 4H), 7.16 (d, J = 7.94 Hz, 1H); MALDI-TOF (m/z): [M+] calcd for C39H25N3:535.64; Found: 535.4. Anal. calcd for C39H25N3: C 87.45, H 4.70, N 7.84; Found: C 87.28, H 4.66, N 7.77. |
80% | With ammonium acetate; acetic acid; at 120℃; for 2h;Inert atmosphere; | A mixture of <strong>[87220-68-6]9-phenyl-9H-carbazole-3-carbaldehyde</strong> (500.00 mg, 1.85 mmol),phenanthrene-9,10-dione (460.50 mg, 2.21 mmol), aniline(0.50 g), ammoniumacetate (0.60 g, 8.00 mmol), and aceticacid (10 mL) were refluxed under nitrogen in an oil bath.After 2 h, the mixture was cooled and filtered. The solidproduct was washed with an acetic acid/water mixture(1:1, 150 mL) and water. It was then purified by chromatographyusing CH2Cl2/petroleum ether (1:1) as eluent toobtain the product as white powder. Yield: 80%. 1H NMR(500 MHz, DMSO, d): 8.96 (d, J = 7.98 Hz, 1H), 8.91 (d,J = 8.67 Hz, 1H), 8.76 (d, J = 7.28 Hz, 1H), 8.35 (s, 1H), 8.09(d, J = 7.53 Hz, 1H), 7.81-7.76 (m, 4H), 7.73-7.68 (m, 6H),7.64 (d, J = 7.08 Hz, 2H), 7.58 (t, J = 7.69 Hz, 7.08 Hz, 2H),7.48 (t, J = 7.08 Hz, 7.00 Hz, 1H), 7.39-7.31 (m, 4H), 7.16(d, J = 7.94 Hz, 1H); MALDI-TOF (m/z): [M+] calcd forC39H25N3:535.64; Found: 535.4. Anal. calcd for C39H25N3:C 87.45, H 4.70, N 7.84; Found: C 87.28, H 4.66, N 7.77. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With ammonium acetate; acetic acid; at 120℃; for 8h;Inert atmosphere; | A mixture of 9,10-phenanthrenequinone (0.8 g, 3.83 mmol), 40-bromo-[1,10-biphenyl]-4-carbaldehyde (1 g, 3.83 mmol), 4-(tertbutyl)aniline (0.57 g, 3.83 mmol) and ammonium acetate(1.8 g,23 mmol) was dissolved in acetic acid (50 mL), and was heated toreflux for 8 h under nitrogen atmosphere. After cooling to roomtemperature, the mixture was poured into water. The solid productwas filtered, washed with methanol and dried under vacuum toafford a pale-yellow solid (1.8 g, yield: 80%). The crude product wasused in the next step without further purification. 1H NMR(400 MHz, CDCl3) δ [ppm]: 8.92 (s, 1H), 8.77 (d, J = 8.4 Hz, 1H), 8.71(d, J = 8.4 Hz, 1H), 7.76 (t, J = 7.6 Hz, 1H), 7.70-7.62 (m, 5H),7.56-7.43 (m, 9H), 7.29-7.25 (m, 1H), 7.19 (d, J = 8.0 Hz, 1H), 1.46 (s,9H); HRMS (APCI): calculated for C37H29BrN2, 582.1494; found,583.1540, [MH]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With ammonium acetate; acetic acid; at 140℃; for 48h;Inert atmosphere; | In a round-bottomed flask, compound B (0.65 g, 2.4 mmol), compound F (0.54 g, 2 mmol), phenanthrene-9,10- dione (0.50 g, 2.4 mmol), ammonium acetate (1.54 g, 20mmol), and a stir bar were added, and then acetic acid wasadded (80 mE). Afier reacting two days in nitrogen atmosphere and 140 C., the mixture was cooled to room temperature and added in water to precipitate a crude product.Filtering was performed using a ceramic flannel, and excessacetic acid was washed away with water, and then impuritieswere washed away with methanol. Lastly, the filter mediumwas purified via sublimation at a temperature of 350 C. andpressure of 7x106 torr to obtain a yellow brown glassycompound PIACzph (0.83 g, yield: 58%). Spectral data of compound PIACzph: 1H NMR (400MHz, CDC13): ö 8.97 (d, J=8.0 Hz, 1H), 8.85 (d, J=8.4 Hz,1H), 8.76 (d, J=8.0 Hz, 1H), 8.54 (s, 1H), 8.46 (s, 1H), 8.09(d, J=7.6 Hz, 2H), 8.05 (d, J=8.4 Hz, 1H), 7.95 (d, J=8.4 Hz,1H), 7.85-7.76 (m, 4H), 7.70-7.58 (m, 9H), 7.55-7.39 (m,9H), 7.31-7.28 (m, 1H), 6.95 (t, J=7.6 Hz, 1H). 13C NMR (175 MHz, CDC13): ö 152.01, 141.36, 140.97,140.41, 138.59, 137.57, 137.31, 135.10, 133.06, 131.28,131.26, 129.98, 129.88, 129.57, 129.26, 128.65, 128.46,128.25, 128.07, 127.99, 127.73, 127.33, 127.30, 127.08,126.35, 126.23, 126.07, 125.97, 125.90, 125.56, 125.26,125.20, 124.79, 124.29, 123.31, 123.19, 123.16, 123.14,122.84, 122.25, 121.60, 120.92, 120.52, 120.40, 110.06,109.71. HRMS(FABj: [M] calcd. for C53H34N3, 712.2674.found, 712.2753. Anal. calcd. For C53H33N3: C, 89.42; H, 4.67; N, 5.90.found: C, 89.37; H, 4.65; N, 5.95. |
58% | With ammonium acetate; acetic acid; at 140℃; for 48h;Inert atmosphere; | Compound B (0.65 g, 2.4 mmol), compound F (0.54 g, 2 mmol), (phenanthrene-9, 10-dione) (0.50 g, 2.4 mmol) were added to a round bottom flask.Ammonium acetate (1.54 g, 20 mmol) and magnet, followed by acetic acid (80 mL).After reacting for two days under a nitrogen atmosphere at 140 C, it was cooled to room temperature and poured into water to precipitate a crude product.Filtration was carried out using a ceramic funnel, and excess acetic acid was washed with water, and the impurities were washed away with methanol.Finally, the filter is sublimed and purified at a temperature of 350 C and a pressure of 7 × 10 -6 torr.The compound PIACzph (0.83 g, yield 58%) was obtained as a yellow brown glass. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With ammonium acetate; acetic acid; at 140℃; for 48h;Inert atmosphere; | Compound B (0.65 g, 2.4 mmol), Compound H (0.54 g, 2 mmol), (phenanthrene-9, 10-dione) (0.50 g, 2.4 mmol) were added to a round bottom flask.Ammonium acetate (1.54 g, 20 mmol) and magnet, followed by acetic acid (80 mL).After reacting for two days under a nitrogen atmosphere at 140 C, it was cooled to room temperature and poured into water to precipitate a crude product.Next, filtration was carried out using a ceramic funnel, and excess acetic acid was washed with water, and most of the impurities were washed away with methanol.Finally, the filtrate was sublimed and purified under the conditions of a temperature of 380 C and a pressure of 7 × 10 -6 torr to obtain a brown glassy compound PIACz (0.93 g, yield: 65%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With ammonium acetate; In acetic acid; at 115℃; for 10h;Inert atmosphere; | (1) In a 500 ml three-necked flask, phenanthrenequinone (31.23 g, 150 mmol), aniline (16.76 g, 180 mmol),4'-Bromo-[1,1'-biphenyl]-4-benzaldehyde (47.00 g, 180 mmol), ammonium acetate (23.12 g, 300 mmol) was dissolved in 300 mL of acetic acid and added to the reactor.Under a nitrogen atmosphere, the temperature was raised to 115 C for 10 h.The liquid phase monitors the reaction and is cooled to room temperature.It was washed twice with water, filtered, and recrystallized twice from ethyl acetate to give 70.15 g of Intermediate A, yield 89%. |