3-oxo-1,2-naphthoquinone analog, its preparation method and application
An analogue, oxo-generation technology, applied in the field of medicinal chemistry, can solve problems such as uncontrollable antibiotics and patient death, and achieve the effect of treating and preventing cardiovascular and cerebrovascular diseases
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Embodiment 1
[0030] Example 1: 3-methoxyl-1,2-naphthoquinone (I, R 1 =R 2 =R 3 =R 4 =R 5 = H; R 6 = Me)
[0031] To a solution of 3-methoxy-2-naphthol (0.60 g, 3.4 mmol) in acetic acid (50 mL) was slowly added dropwise 95% fuming nitric acid (0.48 g, 6.8 mmol) at room temperature. After the dropwise addition, the reaction was continued for 15 min, quenched with water, and extracted three times with 100 mL of dichloromethane. The organic phases were combined and washed three times with 100 mL of water. After drying over anhydrous sodium sulfate, the solvent was evaporated and separated by column chromatography (petroleum ether: ethyl acetate = 3:1) to obtain the red solid compound 3-methoxy-1,2-naphthoquinone (1) (0.27 g , 42%). Melting point: 173-177°C; 1 H NMR (300 MHz, CDCl 3 ) δ: 8.02 (1H, d, J = 6.9 Hz), 7.58 (1H, td, J = 7.5, 0.9 Hz), 7.34 (1H, t, J = 7.5 Hz), 7.24 (1H, d, J = 7.5 Hz), 6.46 (1H, s), 3.88 (3H, s); 13 C NMR (75 MHz, CDCl 3 ) δ: 178.3, 176.3, 151.8, 13...
Embodiment 2
[0032] Example 2: Benzo[f]chroman-5,6-dione (I, R 1 =R 2 =R 3 =R 4 = H; R 5 +R 6 = -CH 2 CH 2 CH 2 -)
[0033] 5-Hydroxybenzo[f]chromane (69 mg, 0.35 mmol) was dissolved in 2 mL of glacial acetic acid, and 0.05 mL of concentrated nitric acid was added dropwise under ice-cooling, the color of the solution turned red, and the reaction was stopped rapidly. Add water to quench. Extracted several times with ethyl acetate, combined the organic phases, dried over anhydrous sodium sulfate, and distilled off the solvent. The crude product was separated by column with petroleum ether: ethyl acetate = 2:1 eluent to obtain the red solid compound benzo[f]chromane-5,6-dione (2) (51 mg, 69 %). Melting point: 145-147 ℃; 1 H NMR (300 MHz, CDCl 3 ) δ: 8.01 (1H, dd, J = 8.0, 1.5 Hz), 7.59 (1H, td, J = 7.5, 1.5 Hz), 7.33 (2H, m), 4.24 (2H, t, J = 5.4 Hz), 2.67 (2H, t, J = 6.6 Hz), 2.13 (2H, m); 13 C NMR (75 MHz, CDCl 3 ) δ: 178.7, 175.1, 147.7, 136.1, 136.0, 129.9, 128.4, 128...
Embodiment 3
[0034] Example 3: 2-Methylnaphtho[2,1-b]dihydrofuran-4,5-dione (I, R 1 =R 2 =R 3 =R 4 = H, R 5 +R 6 = -CH 2 CHCH 3 -)
[0035] Dissolve 2-methyl-4-hydroxynaphtho[2,1-b]dihydrofuran (69 mg, 0.35 mmol) in 2 mL of glacial acetic acid, add 0.05 mL of concentrated nitric acid dropwise under ice-cooling, and see the solution After the color turns red, stop the reaction quickly and add water to extract it. After several extractions with ethyl acetate, the combined organic phases were dried over anhydrous sodium sulfate and the solvent was distilled off. The crude product was separated by column with petroleum ether: ethyl acetate = 3:1 eluent to obtain 2-methylnaphtho[2,1-b]dihydrofuran-4,5-dione (3) (47 mg , 65%). 1 H NMR (300 MHz, CDCl 3 ) δ: 7.97 (1H, dd, J = 7.5, 1.2 Hz), 7.55 (1H, td, J = 7.5, 1.2 Hz), 7.33 (1H, td, J = 7.5, 1.2 Hz), 7.06 (1H, dd , J = 7.5, 1.2 Hz), 5.12-5.02 (1H, m), 3.33 (1H, dd, J = 18.3, 9.9 Hz), 2.79 (1H, dd, J = 18.3, 8.1 Hz), 1.54 (3H, d...
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