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Coumarone derivative, and preparation method and applications thereof

A technology of benzofuran and carboxylic acid derivatives, which can be used in drug combinations, pharmaceutical formulas, and medical preparations containing active ingredients. question

Inactive Publication Date: 2013-10-02
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

These AChE inhibitors can temporarily alleviate the symptoms of mild to moderate patients by enhancing the function of the cholinergic system, but are less effective or ineffective for severe patients; some also have short half-lives and side effects of the peripheral cholinergic system
In addition, the existing AChE inhibitors are symptomatic drugs designed only for a single factor, and have a single molecular target, which cannot effectively prevent the pathological degeneration of AD.

Method used

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  • Coumarone derivative, and preparation method and applications thereof
  • Coumarone derivative, and preparation method and applications thereof
  • Coumarone derivative, and preparation method and applications thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Embodiment 1 (preparation of benzofuran)

[0023] (1) Preparation of oleanol shown in chemical formula (II)

[0024] Take 2.1 kg of Jasmine fruit coarse powder, add ethyl acetate (EtOAc) for ultrasonic extraction at room temperature (2000 mL×3, 40 kHz, 45 min), and concentrate under reduced pressure to obtain ethyl acetate (597.7 g) extracts respectively.

[0025] Ethyl acetate extract (30g) was dissolved in 10% NaOH ethanol (50%) solution (300ml), magnetically stirred, and refluxed at 100°C for 4h under the protection of argon. Cool to room temperature, and concentrate by rotary evaporation to remove ethanol to obtain an aqueous solution; dichloromethane is added to the aqueous solution for extraction to obtain a dichloromethane extract. Anhydrous sodium sulfate was added to the dichloromethane extract to dry, and the dichloromethane was removed by rotary evaporation to obtain a white crude product. The crude product was subjected to silica gel column chromatography. ...

Embodiment 2

[0047] Example 2 (biological activity of benzofuran represented by formula (I))

[0048] (1) In vitro activity test of acetylcholinesterase

[0049] The in vitro inhibitory activity of the compound on acetylcholinesterase (recombinant human rhAChE, Sigma) was determined by Ellman spectroscopy. The inhibitory activity of the compounds on hAChE was determined on a 96-well plate. All solvents were brought to room temperature 25°C before use. Sodium phosphate buffer containing dithionitrobenzoic acid (200 μL, 0.1 M, pH=8), rhAChE solution (13 μL, 100 U / mL), and test compound solution dissolved in DMSO (2 μL, 10 After mixing at room temperature at 25°C, thioacetylcholine iodide solution (20 μL, 7.5 mM) was added to each well to start the reaction, and the absorbance value was measured at 412 nm with a multifunctional microplate reader (Molecular Devices Max384Plus) immediately. Use SoftMaxPro software to reference and calculate IC 50 Value, experiment with DMSO as blank control...

Embodiment 3

[0069] Embodiment 3 (injection)

[0070] formula

[0071] Benzofuran represented by chemical formula (I): 100mg

[0072] Triglycerides: 25mg

[0073] Propylene glycol: 25mg

[0074] Soy lecithin: 25mg

[0075] Preparation:

[0076] Weigh the benzofuran, triglyceride, soybean lecithin and propylene glycol represented by the chemical formula (I) of the prescription amount, heat and dissolve at 45°C to obtain a uniform solution, slowly and gradually introduce the solution into 500mL sterilized distilled water under magnetic stirring , emulsified for 60 minutes to form a clear solution. Then, under sterile conditions, filter with a 0.22μM microporous membrane, fill in a sterilized 50mL ampoule, pull the seal, and place it in 121°C and 0.1MPa autoclaving for 15 minutes to obtain compound I as an active ingredient. The injection can be used to treat diseases such as neurodegenerative diseases such as senile dementia.

[0077] Dosage: Intravenous injection, 1 stick at a time,...

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Abstract

The invention discloses a coumarone derivative represented by formula (I). The coumarone derivative is prepared by reacting 4-amino-1-benzylpiperidine with a carboxylic acid derivative prepared by oxidation of oleanolic alcohol with chromium trioxide. The coumarone derivative can be used for preparation of an inhibitor for aggregation of acetylcholinesterase and amyloid protein.

Description

technical field [0001] The invention belongs to the field of organic chemistry and relates to benzofuran compounds, in particular to a novel benzofuran derivative. Background technique [0002] Alzheimer's disease (AD) is a degenerative central nervous system disease characterized by progressive cognitive and memory dysfunction, also known as Alzheimer's disease. With the aging of the world's population and the increasing severity of environmental pollution, its incidence is increasing day by day. Among the population over 60 years old, the proportion of dementia patients is as high as 5-10%, with a total of tens of millions of people. It is the fourth leading cause of death after cardiovascular diseases, tumors and strokes. [0003] The pathogenesis of AD is extremely complex. It is generally accepted that the onset of AD is a gradual process involving multiple etiological factors. The main pathological changes are senile plaques caused by abnormal deposition of extracellu...

Claims

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Application Information

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IPC IPC(8): C07D405/14A61K31/4525A61P25/28
Inventor 刘嘉炜弗朗索瓦丝·格丽特文森特·杜蒙特司马贞华李武国陈蔚文
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE