Cannabidiol 2-dioxopiperazine acid ester and application thereof
A technology of dioxypiperazine ester and cannabidiol, which is applied in the field of novel cannabidiol derivatives and their preparation, can solve the problems of inability to meet the needs of drug development, ambiguity and the like, and achieves high yield, good stability, The effect of cheap and easily available raw materials
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Embodiment 1
[0039] Embodiment 1, the preparation of cannabidiol-2-dioxopiperazine ester
[0040] The synthetic route is shown in the following formula:
[0041]
[0042] Add 1.02 g (5 mmol) of 4-ethyl-2,3-dioxo-1-piperazinecarbonyl chloride and 20 mL of anhydrous acetonitrile into a 50 mL three-neck flask, stir, add 1.57 g (5 mmol) of cannabidiol and 1 mL of pyridine, stirred and heated, refluxed for 11 hours, concentrated by rotary evaporation, dissolved in dichloromethane, washed with water, dried over anhydrous magnesium sulfate, rotary evaporated, separated and purified by column chromatography, 1.71 g of colorless liquid was obtained, yield 70.9% .
[0043] The H NMR spectrum of the product is characterized as follows:
[0044] 1 H NMR (300 MHz, DMSO- d 6 ) δ : 9.43 (s, 1H), 6.49 (s, 1H), 6.33 (s, 1H),5.04 (s, 1H), 4.43 (d, J = 6.0 Hz, 2H), 3.97 (t, J = 6.0 Hz, 2H), 3.83 (s,1H), 3.64 (s, 2H), 3.42 (t, J = 7.5 Hz, 2H), 2.77 (s, 1H), 2.43 (t, J = 7.5Hz, 2H), 1.99 ( s, 1H), ...
Embodiment 2
[0048] Example 2, Determination of the conversion risk of cannabidiol-2-dioxopiprazinate
[0049] Compound cannabidiol-2-dioxypiperazine and its analogs (cannabidiol-2-propionate, cannabidiol-2-butyrate, cannabidiol-2-imidazole) obtained in embodiment 1 -1-formic acid ester) take appropriate amount respectively (chemical formula such as figure 1 shown), add 20 mL of 95% ethanol solution to dissolve, adjust the pH to 1.68 with 37% hydrochloric acid, take 20 μL and add methanol to 1 mL, put it on the machine, and take samples every 2 hours. With the THC methanol solution of 100 μg / mL and the cannabidiol methanol solution of 100 μg / mL as the reference substance solution, the liquid chromatography detection results of THC and cannabidiol mixed standard samples are as follows: figure 2 shown. Liquid phase conditions: Agilent ZORBAX SB-C18 chromatographic column, elution conditions: 0.1% formic acid solution: acetonitrile = 25:75, time 30 minutes, wavelength 220 nm, injection vol...
Embodiment 3
[0051] Example 3, Determination of the Nerve Cell Injury Protective Effect of Cannabidiol-2-dioxopiperazinate
[0052] Under sterile conditions, the compound cannabidiol-2-dioxopiperazine and its analogs (cannabidiol, cannabidiol-2-propionate, cannabidiol-2-butyl) obtained in Example 1 ester, cannabidiol-2-imidazole-1-carboxylate) were dissolved in DMSO to prepare a 20 mM stock solution. Glial cells BV2 were inoculated into a 96-well plate, respectively stimulated with glutamate and corticosterone to construct a cell injury model, and after 12 hours of culture, cannabidiol and the compound obtained in Example 1 were added to the medium and diluted to 5.0, 2.5, 1.0, 0.5, 0.25, 0.1 μM, set 5 duplicate wells for each group, continue to cultivate for 72 hours, add 20 μL of MTT reagent to each well, and continue to cultivate for 0.5 hours. Discard the MTT working solution, add 150 μl DMSO to each well, and shake gently on a shaker at room temperature for 10 minutes to mix well. T...
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