A kind of cannabidiol-2-nicotinate and its application
A technology of cannabidiol and nicotinic acid ester, which is applied in the field of new cannabidiol derivatives and its preparation, can solve problems such as ambiguity and inability to meet the needs of drug development, and achieve good stability, high yield, and low energy consumption Effect
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0039] Embodiment 1, the preparation of cannabidiol-2-nicotinate
[0040] The synthetic route is shown in the following formula:
[0041]
[0042] Add 0.88 g (5 mmol) of 6-chloronicotinoyl 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, stir to raise the temperature, and reflux for 7 hours. Concentrate by rotary evaporation, dissolve with dichloromethane, wash with water, dry over anhydrous magnesium sulfate, rotary evaporate, and separate and purify by column chromatography to obtain 1.26 g of a colorless liquid with a yield of 55.5%.
[0043] The H NMR spectrum of the product is characterized as follows:
[0044] 1 H NMR (300 MHz, CDCl 3 ) δ : 9.15 (d, J = 3.0 Hz, 1H), 8.37 (q, J = 4.0Hz, 1H),7.51 (d, J = 6.0 Hz, 1H), 6.91 (s, 1H), 6.63-6.51 (m, 1H), 5.25 (s,1H), 4.61 (s, 1H), 4.47 (s, 1H), 4.13 (d, J = 9.0 Hz, 1H), 3.52 (t, J = 9.0Hz, 1H), 2.63- 2.51 (m, 3H), 2.05 (s, 1H), 1...
Embodiment 2
[0048] Example 2, Determination of the conversion risk of cannabidiol-2-nicotinate
[0049] Compound cannabidiol-2-nicotinate and its analogues obtained in Example 1 (cannabidiol-2-propionate, cannabidiol-2-butyrate, cannabidiol-2-imidazole-1- Formate) 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 conditions: chromatographic column is Agilent ZORBAX SB-C18, elution condition is 0.1% formic acid solution: acetonitrile=25:75, time 30 minutes, wavelength 220nm, injection volume 1 μL. Results are expre...
Embodiment 3
[0051] Example 3, Determination of the glial cell damage protection effect of cannabidiol-2-nicotinate
[0052] Under sterile conditions, the compound cannabidiol-2-nicotinate obtained in Example 1 and its analogs (cannabidiol, cannabidiol-2-propionate, cannabidiol-2-butyrate, Cannabidiol-2-imidazole-1-carboxylate) was dissolved in DMSO to make 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. The experiment consis...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More