Novel chalcone compound Chalcone-1203, and composition, preparation method and application thereof

A compound and chalcone technology, applied in the field of novel chalcone compounds, can solve the problems of unpleasant side effects, restricting long-term use, etc., and achieve the effects of simple preparation method, reduced immobility time, and quick effect

Inactive Publication Date: 2016-07-20
ZHEJIANG OCEAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] At present, many drugs are available for antidepressant in clinical application, such as amitepine, clomipramine, moclobemide, fluoxetine, paroxetine, sertraline, citalopram, etc., although these Drugs can be used to treat or alleviate the pain of various depression patients to varying degrees, but they have side effects and discomfort, which limits their long-term use

Method used

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  • Novel chalcone compound Chalcone-1203, and composition, preparation method and application thereof
  • Novel chalcone compound Chalcone-1203, and composition, preparation method and application thereof
  • Novel chalcone compound Chalcone-1203, and composition, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1: Preparation of novel chalcone compound (Chalcone-1203)

[0024] Add 0.425g3.82mmol1-naphthaldehyde to 0.5g3.18mmol compound I, mix well, add dropwise a solution of 14% KOH made of 35mL absolute ethanol and 4.9gKOH, and react at room temperature for 8h. After the reaction is over, pour the reaction solution into 60 mL of ice water, adjust the pH to neutral with 3 mol / L HCl, filter to obtain a yellow solid, and dry it. The crude product is recrystallized with 95% ethanol to obtain a yellow crystal, which is the desired novel chalcone Compound (Chalcone-1203).

[0025] Yield 85.4%, melting point 137.5-138.5°C. 1 HNMR (CDCl 3 )δ: 1 H-NMR (CCl 3 D) δ: 1.70(s, 3H, -CH 3 ), 1.75 (s, 3H, -CH 3 ), 4.51(d, 2H, -CH 2 ), 5.42 (t, 1H, =CH), 6.45-7.86 (m, 3H, -C 6 h 3 ), 7.49 (d, 1H, J = 15Hz, = CH), 7.19-7.49 (m, 7H, -C 12 h 7 ), 8.68 (d, 1H, J=15Hz, =CH), 13.43 (s, 1H, -OH); IR(KBr) cm －1 : 3216, 1638, 1571, 1224, 966; MSm / z: 359 (M+1).

Embodiment 2

[0026] Example 2: Antidepressant pharmacological experiments of novel chalcone compounds

[0027] In this example, mice injected with the above-mentioned novel chalcone compound (Chalcone-1203) were screened by forced swimming test and mouse tail spin test to evaluate its antidepressant efficacy and safety.

[0028] Experimental materials: healthy Balb / e mice, male, weighing 18-20 g, provided by the Animal Experiment Center of Zhejiang Academy of Medical Sciences, and kept at 25°C. During the experiment, free drinking water and food were kept, the temperature of the feeding environment was 24±1°C, and the humidity was 55±5%. The experiment was carried out after 5-7 days of adaptive feeding, and each animal was only used once.

[0029] Positive control drug: FLU (fluoxetine), purchased from Lilly Company of the United States, fluoxetine in the following tests 2.1 and 2.2 was formulated into a solution with normal saline before use, and the chalcone compound (Chalcone-1203) was ...

Embodiment 3

[0037] Embodiment 3: Mouse open experiment

[0038] The open experiment is mainly used to evaluate the autonomous activity behavior of experimental animals. In this embodiment, the open experimental device is an opaque plastic box (80cm × 60cm × 30cm), and the bottom of the plastic box is divided into 48 square grids with a size of 10cm × 10cm. Place the plastic box in a quiet room and light it with a 60W light bulb, which is about 1m above the center of the plastic box.

[0039] Twenty male Balb / e mice were randomly divided into two groups, 10 in each group, which were blank control group and drug group. 30 minutes before the test, the new chalcone compound was dissolved in DMSO solution, and 0.10ml / 20g was intraperitoneally injected at a dose of 10mg / kg, and the blank control group was intraperitoneally injected with the same volume of DMSO solution. Place the mouse in the center square at the bottom of the plastic box, manually record the number of times of movement (all l...

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PUM

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Abstract

The invention relates to a novel chalcone compound Chalcone-1203, and also relates to a preparation method for the compound, a composition using the compound as an active component and application of the compound in preparation of an antidepressant drug. The novel chalcone compound Chalcone-1203 provided by the invention has substantial anti-depression effect. Results of animal testing in the embodiments show that Chalcone-1203 can substantially reduce immobility time of mice in forced swimming test and tail suspension test of the mice, has fast action and small toxic and side effect (TD50>2000 mg / kg), is suitable for long-term usage and shows valuable antidepressant pharmacological properties. The novel chalcone compound uses widely-available and cheap raw materials, is simple to prepare and can be used for preparation of antidepressant drugs of a variety of dosage forms.

Description

technical field [0001] The present invention relates to a novel chalcone compound, in particular to Chalcone-1203[1-(2-hydroxyl-4-prenyloxy)-phenyl-3-(naphthalene-1-yl)-2-propene- 1-ketone], and relates to its preparation method, and its composition as an active component and its application in the treatment of antidepressants. Background technique [0002] Depression, also known as depressive disorder, is characterized by marked and persistent low mood as the main clinical feature. It is the main type of mood disorder. Clinically, it can be seen that the low mood is not commensurate with the situation. The depression of mood can range from gloomy to heartbroken, low self-esteem, depression, and even pessimism World-weary, there may be suicide attempts or behaviors, and even stupor. Some cases have obvious anxiety and motor agitation, and severe cases have hallucinations, delusions and other psychotic symptoms. Depression can affect people's digestive, immune and nervous sy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/84C07C45/72A61K31/122A61P25/24
Inventor 关丽萍金晴昊甄兴华赵水莲彭舟
Owner ZHEJIANG OCEAN UNIV
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