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(+)-4-methoxybornyl benzoate and its preparation method and application

A technology of methoxybenzoic acid and p-toluenesulfonic acid, which is applied in the field of benzoic acid esters, can solve the problems of unsatisfactory ability of borneol to penetrate the blood-brain barrier and limit applications, and achieve the goal of promoting the penetration of blood-brain barrier drugs , low cytotoxicity, and good effect of penetrating the blood-brain barrier

Inactive Publication Date: 2011-12-14
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the ability of borneol to penetrate the blood-brain barrier is still not ideal.
In addition, borneol also has certain reproductive toxicity, which limits its application.

Method used

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  • (+)-4-methoxybornyl benzoate and its preparation method and application
  • (+)-4-methoxybornyl benzoate and its preparation method and application
  • (+)-4-methoxybornyl benzoate and its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] 1. Synthesis of (+)-4-methoxybornyl benzoate

[0014] Add 20g of natural borneol, 15g of 4-methoxybenzoic acid and 30ml of toluene into a 500ml round bottom flask; add 0.5g of p-toluenesulfonic acid dropwise, mix well; stir and reflux at 120°C for 8 hours. After the reaction, the catalyst, unreacted borneol, and solvent were removed to obtain the initial product. The primary product was separated with a silica gel column to obtain colorless crystals.

[0015] 2. Properties of (+)-4-methoxybornyl benzoate

[0016] The colorless crystals obtained in step 1 are poorly soluble in water, but easily soluble in chloroform, ethanol, acetone, and ethyl acetate. The melting point is 66.3-68.6°C.

[0017] 3. Identification of the compounds of the present invention:

[0018] 1. UV spectrum analysis: the compound described in the invention is dissolved in methanol, and then scanned with a PDA-100 diode array detector (DAD), and the compound has ultraviolet absorption at 212.3nm ...

Embodiment 2

[0035] 1. Acute toxicity test of dextroborneol in mice

[0036] 1.1. Experimental animals

[0037] 60 Kunming white mice, half male and half male, body weight 20±2g. Provided by the Guangdong Provincial Laboratory Animal Center, certificate number: SCXK Yue 2008-0001 Yue Jian Zheng Zi 2007A013, used for the test after 3 days of adaptation.

[0038] 1.2. Experimental method

[0039] Mice were fasted overnight for 15 h before administration, and had free access to water. They were divided into 6 groups with 10 rats in each group. Groups 1 to 5 were given dextroborneol blended oil solution, and the dosages were 6170, 4319, 3023, 2116, 1481 mg / kg; Blend oil. According to the weight of the mice, the drug group was fed with dextroborneol at a dose of 0.2 mL / 10 g, and the control group was fed with the same volume of edible oil. Return to normal feeding 2 hours after administration, observe continuously for 14 days, observe the changes in the weight of the mice every day, whethe...

Embodiment 3

[0063] Experimental Study of (+)-4-Methoxybornyl Benzoate Penetrating the Blood Brain Barrier

[0064] 1. Test animals: SPF grade Kunming mice, half male and half male, weighing 20±2g. Provided by the Experimental Animal Center of the Guangdong Provincial Department of Health, certificate number: SCXK Yue 2008-0002, used for experiments after 3 days of adaptation. Kunming mice were fasted overnight for 15 hours before administration, and had free access to water.

[0065] 2. Method

[0066] 2.1 Liquid preparation

[0067] Accurately weigh 40mg of Evans blue and transfer it into a 10ml volumetric flask, add normal saline to the volume to obtain a 0.4% solution; mix acetone and normal saline (7:3) (v:v) to obtain a homogeneous solution slurry mixture.

[0068] 2.2 Evansland standard curve drawing

[0069] Prepare Evans blue multiple release series concentration solution 0.5ug / g, 10ug / g, 20ug / g, 50ug / g, 100ug / g with blank mouse brain plasma, and measure the absorbance at 620...

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Abstract

The present invention relates to a kind of bornyl benzoate and its preparation method and application, its chemical structure is shown in following formula (I), and chemical name is (+)-4-methoxybornyl benzoate. The synthetic method of bornyl benzoate of the present invention is that (+)-borneol, 0.75 times of borneol quality 4-methoxybenzoic acid, 0.025 times of borneol quality p-toluenesulfonic acid are added in toluene, It was obtained by reacting at 120°C for 8 hours. The (+)-4-methoxybornyl benzoate of the present invention has low cytotoxicity and the effect of penetrating the blood-brain barrier, and can promote medicines to penetrate the blood-brain barrier.

Description

technical field [0001] The invention relates to benzoic acid esters, in particular to benzoic acid esters containing six-membered rings. Background technique [0002] Borneol is a commonly used adjuvant in traditional Chinese medicine. Traditional Chinese medicine believes that it has the effects of resuscitating the mind, clearing away heat, relieving pain, and promoting muscle growth. Since ancient times, it has been widely used by various physicians to treat dizziness due to fever, internal closure of phlegm heat, stroke due to summer heat, and convulsions in children. Its main pharmacological effects include 1. anti-inflammatory and analgesic effects; 2. antibacterial and antiviral effects; 3. anti-fertility effects. [0003] Modern medical research shows that borneol can significantly loosen the tight junctions between the cells of the blood-brain barrier and accelerate the passage of substances between cells; The transport of substances swallowed by cells is accelera...

Claims

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Application Information

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IPC IPC(8): C07C69/92C07C67/08A61P43/00
Inventor 王宁生吴祈德宓穗卿李伟荣赵威伍海涛
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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