Application of 2,6-Diisopropylbenzoic Acid and Its Derivatives as Neuroprotective Agents
A neuroprotection and drug technology, applied in nervous system diseases, active ingredients of hydroxyl compounds, drug combinations, etc., can solve problems such as side effects, poor effect, and inability to apply clinically, and achieve protective and strong effects.
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Embodiment 12
[0019] The synthesis of embodiment 12,6-diisopropyl iodobenzene
[0020] Measure 3.2mL (15.8mmol) of 2,6-diisopropylaniline into a 100mL three-necked round-bottomed flask, add 30mL of water, and add 15mL of concentrated hydrochloric acid under mechanical stirring. A solution of 1.18 g (17.4 mmol) of sodium nitrite dissolved in 4 mL was added dropwise to the dropping funnel, and the reaction was continued at 4° C. for 1 h. Weigh 4.40 g (21.28 mmol) of iodine and 6.04 g (36 mmol) of potassium iodide and dissolve them in 10 mL of ice water to obtain a mixed solution. Put the mixed solution into the reaction system, after 30min, add 40mL of water, 100mL of dichloromethane, overnight at room temperature, add 6.30g (25.4mmol) of sodium thiosulfate hydrate, and stir for 20min. The black precipitate was filtered off, the solution was separated with a separatory funnel, the aqueous phase was extracted with chloroform (60mL×2 times), the organic phases were combined, washed with 50mL o...
Embodiment 22
[0021] Synthesis of embodiment 22,6-diisopropylbenzoic acid (1)
[0022] Take 1.44g (5mmol) of 2,6-diisopropyliodobenzene in a 100mL three-neck flask, add 3mL of anhydrous tetrahydrofuran, and fully replace it with nitrogen in the double-pipe system. With acetone as the coolant, the reaction system was lowered to -78°C with liquid nitrogen. With stirring, 5 mL (10 mmol) of 2 mol / L n-butyllithium solution was added dropwise with a syringe, and after the injection was completed, the reaction was kept at -78°C for 1 h. The temperature was raised to room temperature, and after half an hour, CO was 2 Reaction 20h. Add 5 mL of 2N hydrochloric acid solution, stir and extract with ether, combine the organic phases, and evaporate the solvent to dryness. The residue was dissolved in 5 mL of 2N NaOH solution and washed with ether. The aqueous phase was neutralized with 10 mL of 2N hydrochloric acid solution, extracted with ether, and the extracts were combined, dried over anhydrous s...
Embodiment 32
[0023] Example 32, Synthesis of 6-diisopropylbenzyl alcohol (2)
[0024] A solution of 2.1 g (10 mol) of 2,6-diisopropylbenzoic acid dissolved in 10 mL THF was dropped into LiAlH 4 A solution of 0.57 g in 20 mL THF. After adding, reflux for 2h. After cooling, add 10%wtNH 4 20 mL of Cl solution was extracted with EtOAc, washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated to obtain 1.83 g of solid with a yield of 95%. 1 HNMR (CDCl 3 ,500MHZ):1.28(s,12H),2.92-3.12(m,2H),4.79(s,2H),6.86-7.05(m,3H).
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