2,3-dyhydroxyl parabens compound as well as preparation and application thereof

A technology of dihydroxybenzoic acid and ester compounds, which is applied to 2,3-dihydroxybenzoic acid ester compounds and the fields of preparation and application, can solve the problems of large molecular weight, no treatment method, inability to pass through the blood-brain barrier, and the like, achieve the effect of optimizing the structure

Inactive Publication Date: 2010-07-14
ZHEJIANG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, it is a polypeptide composed of more than 100 amino acids; due to reasons such as large molecular weight and strong polarity, it cannot pass through the blood brain barrier (Blood Brain Barrier), and it is difficult to prepare on a large scale, which limits its practical clinical application. , NGF has not found a better treatment method other than direct administration of intracerebral surgery

Method used

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  • 2,3-dyhydroxyl parabens compound as well as preparation and application thereof
  • 2,3-dyhydroxyl parabens compound as well as preparation and application thereof
  • 2,3-dyhydroxyl parabens compound as well as preparation and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] The preparation method of separating and extracting 2,3-dihydroxybenzoate natural compound formula (I) from the traditional Chinese medicine Gentiana, the specific steps are:

[0034] 1) Crushing and extraction:

[0035] After 1980g of traditional Chinese medicine Gentiana was crushed, it was extracted with 10L of methanol (industrial grade) at room temperature for 5 days (with occasional shaking). After suction filtration and concentration, 353.6 g of crude methanol extract was obtained, which was divided into two parts for extraction, and extracted and separated twice with 80% aqueous methanol (1500 ml) and n-hexane (500 ml) alternately. A total of 14.6 g of crude n-hexane layer was obtained.

[0036] 2) Separation and purification:

[0037] The crude sample of the n-hexane layer was first separated twice through a silica gel open column (200-300 mesh, the following solvent systems were all by volume ratio, and the first separation was n-hexane: ethyl acetate=100:0,...

Embodiment 1

[0040] Qualitative identification of the physical and chemical characteristics and chemical structure of compound I-A~L obtained in embodiment 1:

[0041] The structures of compounds I-A and I-B were confirmed by MS, HR MS, 1 H NMR, 13 Confirmed by C NMR, DEPT, H-HCOSY, HMBC, HSQC and HOHAHA.

[0042] The structures of compounds I-C~L were confirmed by MS, HR MS, 1 H NMR test, determined after comparison with the structures of compounds I-A and I-B.

[0043] Physicochemical properties of compound I-A: white solid, molecular formula is C 29 h 50 o 4 ; HR FT-ICR MS: m / z 485.3610 [M+Na] + , theoretical value C 29 h 50 o 4 Na: 485.3601. Infrared spectrum (KBr) values: 3469, 2920, 1671, 1469, 1311 and 1155cm -1 ; Ultraviolet spectrum (solvent is acetonitrile): the maximum absorption wavelength is 318nm; hydrogen spectrum and carbon spectrum data are shown in Table-1.

[0044] Physicochemical properties of compound I-B: white solid, molecular formula C 30 h 52 o 4 ; ...

Embodiment 3

[0077] Biological activity of gentian-derived alkyl 2,3-dihydroxybenzoates.

[0078] In animal models of neurodegeneration, studies have found that NGF can prevent or reduce the degeneration of neurons, prevent the progression of AD to a certain extent, and has the effects of promoting nerve growth and neuroprotection. Because PC12 cells have the general characteristics of nerve cells, PC12 cells will stop dividing under the action of NGF, grow protrusions, and transform into neuron-like cells. Therefore, the compound that can cause PC12 cells to transform into neuron-like cells has application value in the prevention and treatment of neurodegenerative diseases such as senile dementia.

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Abstract

The invention provides a method for separating, extracting and preparing 2,3-dyhydroxyl parabens natural compound from traditional Chinese medicine gentian. The preparation method comprises the following steps of: pulverizing the traditional Chinese medicine gentian, extracting with carbinol, and carrying out suction filteration and concentration to obtain a methanol extract crude product, extracting and separating with 80 percent methanol water solution and normal hexane to obtain normal hexane layer crude sample; and separating the crude sample through a silica gel opening column and separating through an ODS opening column, and purifying by using a reverse HPLC to obtain a target compound. The naturally-separated 2,3-dyhydroxyl parabens compound used as a micromolecule compound represents obvious NGF mimics activity in an in-vitro screening model PC 12 cells for senile dementia, and can be applied to preparing medicaments for preventing neurodegenerative diseases of senile dementia and the like. A structure formula of the compound is shown as the following formula.

Description

technical field [0001] The invention belongs to the preparation method and application of compounds, and relates to a preparation method of 2,3-dihydroxybenzoate natural compounds and the application of such compounds in the prevention and treatment of neurodegenerative diseases such as senile dementia. Background technique [0002] Alzheimer's disease can be roughly divided into three types: Alzheimer's disease (AD for short), vascular dementia and other types of dementia. With the increase of the aging population, the prevalence of Alzheimer's disease has increased significantly, and it has become the fourth leading cause of death in adults, second only to heart disease, cancer, and stroke. It is estimated that there are more than 5 million senile dementia patients in my country, accounting for about 1 / 4 of the total number of cases in the world; moreover, with the acceleration of the aging process of my country's population, this number will become even larger, which will...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C69/88C07C67/56A61K31/235A61P25/28
Inventor 戚建华高丽娟罗燕李金优
Owner ZHEJIANG UNIV
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