Scutellarein derivative and preparing method, preparation and application thereof
A technology of anthocyanidin and cyanidin aglycone is applied in the directions of pharmaceutical formulations, drug combinations, medical preparations containing active ingredients, etc., and can solve the problems of easy oxidative denaturation, low bioavailability, difficult to permeate biological membranes, etc. , to achieve the effect of less environmental pollution, simple and easy preparation method and good reproducibility
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[0025] The preparation method is based on raw material 4-fluorophenylboronic acid, 3-fluorophenylboronic acid, 4-phenylphenylboronic acid, 4-trifluorophenylboronic acid or 4-pyridinium borate in the presence of a palladium catalyst and an organic solvent, and chlorine Substituting trimethoxychromanone for coupling reaction to obtain target scutellarin aglycon derivatives.
[0026] The reaction formula for this reaction is:
[0027]
[0028] A catalyst is a substance that increases the rate of a chemical reaction without permanently changing its structure.
[0029] The palladium catalyst is triphenylphosphopalladium.
[0030] Organic solvents refer to a class of organic compounds that contain carbon atoms and can dissolve water-insoluble substances, including alkanes, alkenes, alcohols, aldehydes, amines, esters, ethers, ketones, aromatic hydrocarbons, hydrogenated hydrocarbons, terpene hydrocarbons, Halogenated hydrocarbons, heterocyclic compounds, nitrogen-containing com...
Embodiment 1
[0042] The preparation of embodiment 1 KPC-4000001
[0043]
[0044] Add compound 7 (300.0 mg, 1.11 mmol), compound 8 (186.0 mg, 1.33 mmol), sodium carbonate (234.9 mg, 2.22 mmol), tetrakis (triphenylphosphine) palladium (64.0 mg, 0.055 mmol) into a reaction flask ), 1,4-dioxane (5.0 mL) and water (0.5 mL), replacing nitrogen. The reaction was carried out at 100 °C for 5 hours, TLC (petroleum ether:ethyl acetate=6:4) showed that the reaction was complete, the reaction solution was poured into ice water (10 mL), and ethyl acetate (5 mL×3), The organic layers were combined, washed once with 10 mL of saturated sodium chloride, dried over anhydrous sodium sulfate, and spin-dried to obtain a crude product that was purified by column chromatography (petroleum ether: ethyl acetate = 6:4) to obtain 200 mg of a white solid. Rate: 55%. 1H NMR : 7.87 (dd, J = 5.3, 8.8 Hz, 2H), 7.19 (t, J = 8.6 Hz, 2 H), (400MHz , CDCl3) 6.80 (s, 1 H), 6.62 (s, 1 H) ,3.98 (s, 3 H), 3.97 (s, 3 H), 3....
Embodiment 2
[0045] Preparation of Example 2 KPC-4000002
[0046]
[0047] Add compound 7 (300.0 mg, 1.11 mmol), compound 9 (186.0 mg, 1.33 mmol), sodium carbonate (234.9 mg, 2.22 mmol), tetrakis(triphenylphosphine) palladium (64.0 mg, 0.055 mmol) into a reaction flask ), 1,4-dioxane (5.0 mL) and water (0.5 mL), replacing nitrogen. The reaction was carried out at 100 °C for 5 hours, TLC (petroleum ether:ethyl acetate=6:4) showed that the reaction was complete, the reaction solution was poured into ice water (10 mL), and ethyl acetate (5 mL×3), The organic layers were combined, washed once with 10 mL of saturated sodium chloride, dried over anhydrous sodium sulfate, and spin-dried to obtain a crude product that was purified by column chromatography (petroleum ether: ethyl acetate = 6:4) to obtain 280 mg of a white solid. Rate: 76%. 1H NMR : 7.65 (d, J = 8.3 Hz, 1 H), 7.62 - 7.57 (m, 1 H), 7.48 (dt, (400MHz , CDCl3) J =5.9, 8.0 Hz, 1 H), 7.22(dt, J = 2.4, 8.2 Hz, 1 H), 6.82 (s, 1 H), 6...
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