Cannabidiol 2-butyrate and application thereof

A technology of cannabidiol and butyrate, which is applied in the preparation of carboxylic acid halides, preparations for toiletry, active ingredients of esters, etc., can solve the biological effects and drug potential that have not been disclosed, and cannot meet the needs of drug development, Biological role is not clear and other issues, to achieve the effect of high yield, mild conditions, low energy consumption

Active Publication Date: 2021-12-03
黑龙江丰佑麻类种植有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

CN112111025A discloses the preparation of cannabidiol derivatives including cannabidiol-3-succinic acid, but this compound only improves its water solubility, and its biological effects and drug-making potential have not been disclosed
CN1688290A discloses the preparation of cannabinoid liquid preparation including cannabidiol-propanol, and its biological effect is still unclear
CN109311838A discloses the biosynthesis of cannabinoid prodrugs including cannabidiol-2-acetate, but these prodrugs still cannot meet the needs of drug development

Method used

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  • Cannabidiol 2-butyrate and application thereof
  • Cannabidiol 2-butyrate and application thereof
  • Cannabidiol 2-butyrate and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Embodiment 1, the preparation of cannabidiol-2-butyrate

[0035] The synthetic route is shown in the following formula:

[0036]

[0037] Add 0.53g (5mmol) of butyryl chloride and 20mL of anhydrous acetonitrile into a 50mL three-neck flask, stir, add 1.57g (5mmol) of cannabidiol and 1mL of pyridine, stir to raise the temperature, reflux for 4 hours, and concentrate by rotary evaporation. Dissolved, washed with water, dried over anhydrous magnesium sulfate, rotary evaporated, separated and purified by column chromatography to obtain 1.39 g of a colorless liquid with a yield of 72.4%.

[0038] The H NMR spectrum of the product is characterized as follows:

[0039] 1 H NMR (300MHz, DMSO-d 6 )δ: 6.41(d, J=24.0Hz, 1H), 6.18(d, J=18.0Hz, 1H), 6.01(s, 1H), 5.05(d, J=21.0Hz, 1H), 4.46(d, J=21.0Hz, 2H), 3.83(d, J=9.0Hz, 1H), 3.03(t, J=9.0Hz, 1H), 2.66(s, 1H), 2.43-2.30(m, 3H), 2.08( s,1H),2.02-1.83(m,2H),1.67(s,2H),1.58(s,7H),1.48(d,J=6.0Hz,2H),1.30-1.26(m,5H),0.95 (t, ...

Embodiment 2

[0043] Example 2, Determination of the Nerve Cell Injury Protection of Cannabidiol-2-butyrate

[0044] Under sterile conditions, the compound cannabidiol-2-butyrate and its analogs (cannabidiol, cannabidiol-2-acetate, cannabidiol-2-imidazole-1- Formate, cannabidiol-2-propyl ether, cannabidiol-2-(3-hydroxy)propionate, cannabidiol-2-bicarbonate, cannabidiol-2-(2-hydroxy)propionate acid ester) was dissolved in DMSO to prepare a 20mM 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...

Embodiment 3

[0056] Embodiment 3, anti-breast cancer effect determination of cannabidiol-2-butyrate

[0057] Under sterile conditions, the compound cannabidiol-2-butyrate and its analogs (cannabidiol, cannabidiol-2-acetate, cannabidiol-2-imidazole-1- Formate, cannabidiol-2-propyl ether, cannabidiol-2-(2-hydroxy)propionate, cannabidiol-2-(3-hydroxy)propionate, cannabidiol-2-carbonic acid Hydrogen ester) was dissolved in DMSO to make a 20mM stock solution. Human breast cancer cells MDA-MB-231 were inoculated into 6-well plates, and three replicate wells were set for each group, and cultured for 12 hours. After the cells adhered to the wall, they were diluted into 5.0, 2.5, and 1.0 μM drug treatment groups by adding medium. Incubate for 24 hours. A normal control group was set up in the experiment. Digest the cells with EDTA-free trypsin, wash twice with PBS, resuspend the cells in 100 μL binding buffer, transfer to the flow tube, then add 5 μL Annexin V-FITC and 5 μL PI staining solution,...

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PUM

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Abstract

The invention discloses cannabidiol 2-butyrate and application thereof, and particularly relates to a compound as shown in a formula I, and a stereoisomer or pharmaceutically acceptable salt thereof. The cannabidiol 2-butyrate has a protection effect on nerve cell injury and skin cell injury, and can induce apoptosis of human breast cancer cells. The compound has practical application value in medicine and cosmetic production.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a novel cannabidiol derivative and its preparation method and application. Background technique [0002] Cannabidiol (CBD) is one of the main phenolic chemical components in industrial hemp. In vivo experiments have found that CBD can not only antagonize the psychoactive activity induced by THC agonizing cannabinoid type I receptor (CB1R), but also has anticonvulsant, Sedative and hypnotic, anxiolytic, antipsychotic, anti-inflammatory and neuroprotective, it is a natural active ingredient with great application prospects in the fields of medicine, cosmetics and food. [0003] In recent years, the physiological activity research and application development of CBD have made great progress. GW Pharmaceuticals UK has developed Sative (an oromucosal spray with a THC / CBD content ratio of 1) for the treatment of tuberous sclerosis (TSC). In 2018, the U.S. Food an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/28C07C67/14A61K31/22A61K8/37A61P25/00A61P35/00A61P17/00A61Q19/00
CPCC07C69/28A61K8/37A61P25/00A61P35/00A61P17/00A61Q19/00
Inventor 王凤忠范蓓孙玉凤佟立涛金诺孙晶卢聪王永泉白亚娟李敏敏李春梅
Owner 黑龙江丰佑麻类种植有限公司
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