Preparation and application of brain glioma targeting berberine and folic acid modified lipid material
A glioma, targeting lipid technology, applied in the field of medical technology and chemical synthesis, can solve the problems of poor plasma stability of nanoparticles, serious cells, toxicity and so on
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Embodiment 1
[0033] Preparation of compound 2
[0034] Compound 1 (19.88 g, 51.40 mmol) was placed in a reaction flask, replaced with argon three times, dissolved in 65 mL of a mixed solvent (52 mL of anhydrous dichloromethane + 13 mL of anhydrous pyridine), and sequentially added succinic anhydride ( 3.30 g, 33.60 mmol), DMAP (632.0 mg, 5.170 mmol), DMAP (632.0 mg, 5.170 mmol), after addition, stirred at room temperature for 16 h, TLC monitored the completion of the raw material reaction, stopped the reaction, added 15 mL of water and continued to stir for 2 h, and added 200 mL of dichloro Methane, and washed with 1N HCl (150 mL×2) and saturated sodium chloride solution (100 mL×1) successively, the organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure to remove the solvent, and the residue was subjected to silica gel column chromatography Purification (petroleum ether: dichloromethane = 3:1) gave 12.30 g of white solid powder with a yield of 49.15%. 1...
Embodiment 2
[0036] Preparation of compound 3
[0037] Compound 2 (21.00 g, 2.055 mmol) was placed in the reaction bottle, replaced with argon three times to dissolve it with 20 mL of anhydrous dichloromethane, and then added dicyclohexylcarbodiimide (DCC, 0.635 g , 3.083mmol), 4-dimethylaminopyridine (DMAP, 0.076g, 0.620 mmol), activated at 0 ℃ for 30 min. Tetraethylene glycol (1.996 g, 10.275 mmol) was dissolved in 3 mL of anhydrous dichloromethane, and the above activation reaction solution was slowly added dropwise under the protection of argon. After the addition was complete, it was moved to room temperature and stirred for 2 h. The completion of the reaction was monitored by TLC, the insoluble matter was removed by filtration, the filtrate was collected and concentrated under reduced pressure to remove the reaction solvent, the residue was dissolved in 10 mL of dichloromethane, and the reaction solution was sequentially washed with 1N HCl (20 mL×2), water (10 mL×1 ), saturated sodi...
Embodiment 3
[0039] Preparation of Compound 4
[0040] The compound monobenzyl succinate (315.63 mg, 1.52 mmol) was dissolved in 8 mL of anhydrous dichloromethane, and 1-(3-dimethylaminopropyl)-3-ethylcarbadiene was added successively under the protection of argon Imine hydrochloride (EDCI, 368.4 mg, 1.92 mmol), 4-dimethylaminopyridine (DMAP, 234.79 mg, 1.92 mmol) and N,N-diisopropylethylamine (DIPEA, 300.4 mg, 2.32 mmol) , activated at 0 °C for 30 min. Compound 3 (670.0 mg, 1.01 mmol) was dissolved in 8 mL of anhydrous dichloromethane, and then transferred to the above reaction solution, moved to room temperature and stirred for 6 h. The reaction was monitored by TLC, and the reaction was stopped. The reaction solution was washed with 1N HCl (20 mL × 2), saturated aqueous sodium bicarbonate solution (20 mL × 1), and saturated sodium chloride solution (10 mL × 1), and the organic layer was collected. After drying over anhydrous sodium sulfate, it was concentrated under reduced pressure t...
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