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Preparation method and application of pongamol

A technology of pangetin and reaction, applied in antipyretics, nervous system diseases, organic chemistry, etc., can solve the problems of expensive starting materials, cumbersome post-processing, and low yield

Active Publication Date: 2019-08-16
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

So far, there are few methods for synthesizing pangetin, and the existing methods have problems such as expensive starting materials, cumbersome post-processing, and low yields.
In addition, so far, there is no relevant literature on the effects of pangkinsein on nerve injury-related diseases (Alzheimer's disease, Parkinson's disease, etc.) and inflammation-related diseases (arthritis, pneumonia, hepatitis, etc.)

Method used

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  • Preparation method and application of pongamol
  • Preparation method and application of pongamol
  • Preparation method and application of pongamol

Examples

Experimental program
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Effect test

Embodiment 1

[0090] (1) Synthesis of 6,7-dihydro-4(5H)-benzofuranone

[0091] Add 1,3-cyclohexanedione (10.0g, 89.18mmol) to a 250mL round bottom flask, dissolve it in 60mL of water, add 20% sodium hydroxide solution 35mL under ice-cooling, then add KI (2.9g, 17.4mmol) , and finally 16 mL of 40% chloroacetaldehyde aqueous solution was slowly added dropwise. Add concentrated hydrochloric acid with a mass fraction of 37.5% to adjust the pH to about 4, add 100mL of water, extract with petroleum ether (100mL×4), combine the organic phases, wash with saturated brine (100mL×3), and finally wash with anhydrous sodium sulfate After drying, the solvent was evaporated to dryness under reduced pressure to obtain 10.0 g of light yellow liquid 7, namely 6,7-dihydro-4(5H)-benzofuranone, with a yield of 82%. 1 H NMR (400MHz, CDCl 3 )δ: 7.32(d, J=2.0Hz, 1H), 6.67(d, J=2.0Hz, 1H), 2.90(m, 2H), 2.52(m, 2H), 2.21(m, 2H).

[0092] (2) Synthesis of 5-acetyl-6,7-dihydro-4(5H)-benzofuranone

[0093] Add 7 (7...

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Abstract

The invention belongs to the field of medicinal chemistry, and relates to a preparation method and application of pongamol. The preparation method comprises the following steps: with 1,3-cyclohexanedione (6) as a starting raw material, carrying out a cyclization reaction to obtain 6,7-dihydro-4-(5H)-benzofuranone (7); carrying out acylation reaction on the compound (7) to obtain 5-acetyl-6,7-dihydro-4-(5H)-benzofuranone (8); carrying out dehydrogenation reaction on the compound (8) to obtain 1-(4-hydroxy-5-benzofuryl) ethyl ketone (3); carrying out methylation reaction on the compound (3) to obtain 1-(4-methoxy-5-benzofuryl) ethyl ketone (4); and condensing the compound (4) with benzoyl chloride to obtain the pongamol. According to the preparation method, the selected reagents are cheap and easy to obtain, the post-treatment method is simple, the reaction conditions are mild, and the product yield is high. Pharmacological activity experiments show that the synthesized compound has nerve injury resistance and anti-inflammatory activity, which means that the compound has a good application prospect in the field of treatment of nerve injury and inflammation related diseases.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and in particular relates to a preparation method and application of pangetin. Background technique [0002] The chemical name of pseudomin is 1-(4-methoxy-5-benzofuran)-3-phenyl-1,3-propanedione, which belongs to chalcone compounds and is isolated from pseudomonas , has antibacterial, anticancer, antioxidative, antidiabetic biological activities, and has high research value. Its structural formula is: [0003] [0004] Chalcones are a class of natural organic compounds that exist in licorice, safflower and other medicinal plants. Their distribution in nature is relatively limited. Naturally occurring chalcones are difficult to extract and obtain, and cannot be widely used. . Therefore, through a large amount of research, various chalcones are usually obtained by artificial synthesis. So far, there are few methods for synthesizing pangetin, and the existing methods have problems such as ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/79A61P25/00A61P29/00
CPCC07D307/79A61P25/00A61P29/00
Inventor 任杰王文斌张美菊胡昆李丽霞袁玲
Owner CHANGZHOU UNIV
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