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Cannabinoid compound as well as preparation method, composition and application thereof

A technology of compounds and substituents, applied in the field of cannabinoids, can solve problems such as inability to form stable π bonds, affect the effect of drug molecules and receptors, and affect biological effects

Active Publication Date: 2020-12-08
SHANGHAI TECH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Silicon is an element of the fourth main group and the third period. It is the same main group as carbon. They are natural bioisosteres. Although both carbon and silicon show the same valence to form tetrahedral compounds, their properties have Certain differences: (1) The C-Si bond is nearly 20% longer than the C-C bond, the C-C bond length is 1.54 angstroms, and the C-Si bond length is 1.87 angstroms, which will affect the effect of drug molecules and receptors; (2) The lipophilicity of silicon is stronger, which can increase the transmittance of the central nervous system; (3) Silicon cannot form stable π bonds, and the bond energy of Si-Siσ bonds (230kJ·mol -1 ) is weaker than the Si-O bond energy (368kJ·mol -1 ), so silicon can form a stable 1,2-gemsilanediol structure; (4) silicon can form compounds with a coordination number of six or higher; (5) the electronegativity of silicon is lower than that of carbon, and the electronegativity of silicon A negativity of 1.74 and a value of 2.50 for carbon will result in a change in the polarity of silicon-containing compounds
These factors will lead to changes in the physicochemical properties of silicon-substituted carbon compounds, affect metabolic properties, and then affect biological effects

Method used

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  • Cannabinoid compound as well as preparation method, composition and application thereof
  • Cannabinoid compound as well as preparation method, composition and application thereof
  • Cannabinoid compound as well as preparation method, composition and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0147] Example 1: 5-(butyldimethylsilyl)-2-cyclohexyl-3-methoxyphenol (compound 1) and 5-(butyldimethylsilyl)-2-cyclohexylbenzene- Synthesis of 1,3-Diphenol (Compound 2)

[0148] Step 1: Synthesis of Butyl(3,5-Dimethoxyphenyl)dimethylsilane

[0149]

[0150] Weigh 1-bromo-3,5-dimethoxybenzene (500mg, 2.3mmol) into a flask, add anhydrous tetrahydrofuran (10mL) under the protection of argon, cool down to -78°C in the low-temperature reactor, and slowly A solution of n-butyllithium in n-hexane (1.60M, 4.3mL, 6.9mmol) was added dropwise. The reaction was stirred at -78°C for half an hour, after which butyldimethylsilyl chloride (1.04 g, 6.9 mmol) was slowly added dropwise. After stirring for 2 hours, move to room temperature and stir for an additional 1 hour. Add a saturated aqueous solution of ammonium chloride (10 mL) to the reaction system to quench the reaction, extract three times with ethyl acetate, combine the organic phases and wash with water and saturated brine, dr...

Embodiment 2

[0160] Example 2: 5-(hexyldimethylsilyl)-2-cyclohexyl-3-methoxyphenol (compound 3) and 5-(hexyldimethylsilyl)-2-cyclohexylbenzene-1, Synthesis of 3-Diphenol (Compound 4)

[0161] Step 1: Synthesis of (3,5-dimethoxyphenyl)(hexyl)dimethylsilane

[0162]

[0163] Weigh 1-bromo-3,5-dimethoxybenzene (500mg, 2.3mmol) into a flask, add anhydrous tetrahydrofuran (10mL) under the protection of argon, cool down to -78°C in the low-temperature reactor, and slowly A solution of n-butyllithium in n-hexane (1.60M, 4.3 mL, 6.9 mmol) was added dropwise. After the reaction solution was stirred at -78°C for half an hour, hexyldimethylsilyl chloride (1.23 g, 6.9 mmol) was slowly added dropwise, stirring was continued for 2 hours, then moved to room temperature and stirred for another 1 hour. Add a saturated solution of ammonium chloride (10 mL) to the reaction system to quench the reaction, extract three times with ethyl acetate, combine the organic phases and wash with water and saturated ...

Embodiment 3

[0173] Example 3: 5-(Butyldimethylsilyl)-2-cyclopentyl-3-methoxyphenol (compound 5) and 5-(butyldimethylsilyl)-2-cyclopentyl Synthesis of Benzene-1,3-diol (Compound 6)

[0174] Step 1: Synthesis of 1-(4-((butyldimethylsilyl)-2,6-dimethoxyphenyl)cyclopentyl-1-ol

[0175]

[0176] Experimental operation is the same as step 2 of embodiment 1.

[0177] Step 2: Synthesis of butyl(4-cyclopentyl-3,5-dimethoxyphenyl)dimethylsilane

[0178]

[0179] Experimental operation is the same as step 3 of embodiment 1. 1 H NMR (800MHz, deuterated chloroform) δ6.66(s,2H),3.82(s,6H),3.66–3.59(m,1H),1.95–1.86(m,2H),1.86–1.79(m,2H ),1.77–1.72(m,2H),1.65–1.59(m,2H),1.36–1.32(m,4H),0.88(t,J=6.8Hz,3H),0.76–0.73(m,2H), 0.25(s,6H).

[0180] Step 3: 5-(butyldimethylsilyl)-2-cyclopentyl-3-methoxyphenol (compound 5) and 5-(butyldimethylsilyl)-2-cyclopentylbenzene Synthesis of -1,3-diphenol (Compound 6)

[0181]

[0182] Experimental operation is the same as step 4 of embodiment 1. Compound...

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Abstract

The invention discloses a cannabinoid compound as well as a preparation method, a composition and application thereof. The invention discloses a compound shown as a formula I or a pharmaceutically acceptable salt thereof. The compound disclosed by the invention has medium-to-strong affinity to a cannabinoid receptor 1 or a cannabinoid receptor 2, and can be used as a potential therapeutic drug fortreating diseases and symptoms related to an endogenous cannabinoid system; , including but not limited to anorexia, vomiting, pain, epilepsy, spasm, Parkinson's disease, Alzheimer's disease, anxiety, depression, schizophrenia, or drug addiction.

Description

technical field [0001] The present invention relates to a cannabinoid compound, its preparation method, composition and use. Background technique [0002] The endocannabinoid system (endocannabinoid system, ECS) is involved in a variety of physiological and pathological processes such as appetite, pain, inflammation, emotion, memory, etc. Drug intervention is a potential method for the treatment of related diseases (Pacher et al., Pharmacological Reviews 2006, 58, 389-462). The endocannabinoid system consists of three parts: cannabinoid receptors, endocannabinoids, and enzymes that regulate the synthesis and metabolism of endocannabinoids. Cannabinoid receptors belong to G protein-coupled receptors (GPCRs) and are mainly divided into two subtypes, cannabinoid receptor 1 (CB1) and cannabinoid receptor 2 (CB2). CB1 receptors are mainly expressed in the central nervous system and are one of the most abundantly expressed GPCRs in the brain. They are also expressed in organs su...

Claims

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Application Information

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IPC IPC(8): C07F7/08A61K31/695A61P1/08A61P25/04A61P25/08A61P25/16A61P25/28A61P25/22A61P25/24A61P25/18A61P25/30A61P1/14
CPCC07F7/081C07F7/0814A61P1/08A61P25/04A61P25/08A61P25/16A61P25/28A61P25/22A61P25/24A61P25/18A61P25/30A61P1/14
Inventor 程建军刘志杰张志远华甜徐越溟
Owner SHANGHAI TECH UNIV
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