Application of polycyclic polyketone compound in preparation of medicine for resisting novel coronavirus
A technology of polyketide compounds and coronaviruses, which can be used in antiviral agents, pharmaceutical formulations, medical preparations containing active ingredients, etc., and can solve the problem of lack of anti-SARS-CoV-2 drugs
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Embodiment 1
[0049] 6,8-Hydroxy-5-(3-methylbutyryl)-9-isobutyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1, Preparation of 3(2H)-diketone (1)
[0050]
[0051] first step
[0052] Dissolve phloroglucinol 26a (2.5 g, 20 mmol) in nitromethane solution at room temperature, add anhydrous aluminum chloride (10.7 g, 80 mmol) and isobutyryl chloride (2.3 g, 22 mmol) successively , and warmed to reflux. After reacting for 12 hours, the reaction solution was slowly poured into ice water, and saturated sodium potassium tartrate solution (100 mL) was added, followed by vigorous stirring. The reaction solution was extracted 3 times with ethyl acetate (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 26c (3.6 g, yield 85%).
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Embodiment 2
[0061] 6,8-Dihydroxy-5-(2-diylbutyryl)-9-isopropyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1 , Preparation of 3(2H)-diketone (2)
[0062]
[0063] Compound 27b (1.0 g, 5 mmol) was dissolved in THF and added to compound 27a (1.8 g, 7.5 mmol) at room temperature. After reacting for 4 hours, p-toluenesulfonic acid monohydrate (2.9 g, 15 mmol) was added, and the temperature was raised to reflux. After reacting for 2 hours, cool down to room temperature, add saturated aqueous sodium bicarbonate (100 mL) to quench the reaction, and extract the reaction solution with ethyl acetate three times (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 2 (964 mg, yield 45%).
[0064] 1 H NMR (500 MHz, CDCl 3 ) δ 13....
Embodiment 3
[0066] 6,8-Dihydroxy-5-(2-methylbutyryl)-9-phenyl-2,2,4,4-tetramethyl-4,9-dihydro-1H-xanthene-1, Preparation of 3(2H)-diketone (3)
[0067]
[0068]Compound 27b (1.0 g, 5 mmol) was dissolved in THF and added to compound 28a (2.0 g, 7.5 mmol) at room temperature. After reacting for 4 hours, p-toluenesulfonic acid monohydrate (2.9 g, 15 mmol) was added, and the temperature was raised to reflux. After reacting for 2 hours, cool down to room temperature, add saturated aqueous sodium bicarbonate (100 mL) to quench the reaction, and extract the reaction solution with ethyl acetate three times (100 mL×3). The organic phases were combined and washed with saturated NaCl solution. After drying and filtering over anhydrous sodium sulfate, the organic phase was evaporated to dryness under reduced pressure. The obtained crude product was separated and purified by silica gel column chromatography to obtain compound 3 (994 mg, yield 43%).
[0069] 1 H NMR (400 MHz, CDCl 3 ) δ 13.50 ...
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