Application of chalcone compounds in preparations of inflammation resisting medicines

A compound and drug technology, applied in the direction of anti-inflammatory agents, drug combinations, active ingredients of ketones, etc., can solve the problem that the pharmacological activity cannot be predicted from the structure

Active Publication Date: 2012-04-04
WENZHOU MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] However, other chalcones structurally similar to chalcones have very different functional activities, and the final pharmacological activities such as anti-inflammatory cannot be predicted from the structure

Method used

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  • Application of chalcone compounds in preparations of inflammation resisting medicines
  • Application of chalcone compounds in preparations of inflammation resisting medicines
  • Application of chalcone compounds in preparations of inflammation resisting medicines

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] The synthesis of embodiment 1 compound

[0027] Dissolve 1 mmol of the corresponding substituted benzaldehyde and substituted acetophenone in 10-20 mL of absolute ethanol, add 5-10 drops of 40% NaOH solution at 5-8°C, react for 5-24 hours at 5-8°C, and detect with TLC The reaction proceeds. After the reaction, 1-2 times the volume of the reaction liquid was added to precipitate a precipitate, which was suction filtered and vacuum-dried overnight to obtain a powder product, which was purified by silica gel column chromatography to obtain compounds with a purity greater than 98%. Among the hundreds of compounds synthesized, the pharmacological activities vary greatly, and the representative compounds and their physicochemical properties are as follows:

[0028] Comparative compound L1H2: (E)-4-(dimethylamino)Chalcone(L1H2).Yellow crystal, 32.4% yield, mp 97.8~98.9℃. 1 H-NMR (CDCl 3 )δ: 8.003(d, J=7.8Hz, 2H, H-2', H-6'), 7.793(d, J=15.6Hz, 1H, H-β), 7.552(d, J=8.4Hz, 2...

Embodiment 2

[0063] Inhibition of the compound of Example 2 on the release of inflammatory factors from macrophages stimulated by LPS

[0064] The preliminary anti-inflammatory activity of the compound in vitro was tested by using the compound to inhibit the release of inflammatory factors (TNF-α and IL-6) from RAW 264.7 macrophages stimulated by LPS. The specific method is as follows: 1.2×10 6 RAW 264.7 macrophages were cultured with DMEM medium at 37°C. After 24 hours, the medium was renewed, and the test compound (final concentration was 10 μM) was added for pretreatment for 2 hours, and then treated with 0.5 μg / mL LPS for 22 hours. , collect the culture fluid and use ELISA method to detect the content of TNF-α and IL-6; collect the cells to detect the total protein concentration, and the ELISA results are divided by the corresponding total protein concentration for calibration, and the TNF-α and IL-6 content of the LPS control group The calibration was 100; each compound was tested thr...

Embodiment 3

[0065]Example 3 The dose-effect relationship of the active compound inhibiting the release of inflammatory factors from macrophages stimulated by LPS

[0066] The dose-effect relationship of active compounds inhibiting the release of TNF-α and IL-6 from RAW 264.7 macrophages stimulated by LPS was further tested. The method was the same as in Example 2. For experimental data, see figure 2 . The inhibitory activities of the compounds on TNF-α and IL-6 all have a good dose-effect relationship, and the IC 50 ICs of IL-6 inhibitory activity were 38.6, 7.32, 8.42, 2.90, 2.76 μM, respectively 50 2.7, 8.22, 5.55, 6.88, and 5.35 μM, respectively. It can be seen that these compounds have medicinal prospects.

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Abstract

The invention belongs to the field of pharmaceutical chemistry, and specifically relates to an application of specific chalcone compounds in the preparations of inflammation resisting medicines and medicines used for treating inflammation-related diseases. With the chalcone compounds, expression and release of various inflammatory factors such as TNF-alpha, IL-6, COX-2, IL-1beta and IL-12 can be inhibited; nuclear translocation of an inflammation-regulation-related nuclear factor -kappaB can be substantially inhibited; and phosphorylation of inflammation signal pathways ERK and p38 can be inhibited. As a result of in-vivo experiments, with the compounds, the survival rate of LPS-introduced mice mortality can be substantially improved.

Description

Technical field: [0001] The invention belongs to the field of medicinal chemistry. Specifically, the invention relates to the application of specific chalcones in the preparation of anti-inflammatory drugs and drugs for treating inflammation-related diseases. These chalcones inhibit various inflammatory factors The expression and release of the protein can achieve good anti-inflammatory effects in vitro and in vivo. Background technique: [0002] Natural chalcones belong to flavonoids, which are widely found in fruits, vegetables and natural medicines, and have various biological activities such as anti-inflammatory, anti-tumor, analgesic, anti-ulcer, anti-bacterial, anti-malarial, and have very low toxicity . For example, Chinese Patent Application No. 200910264515.1 isolated chalcone from Oxytropis falciparum, which has pharmacological activities of inhibiting tumor cell growth, proliferation and inhibiting acute and chronic inflammation. [0003] However, the functional...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K31/136A61K31/12A61P29/00
Inventor 梁广吴建章李校堃
Owner WENZHOU MEDICAL UNIV
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