Analog of mono carbonyl structure of curcumin, and usage

A hydroxyl and halogen technology, applied in the field of structural analogs of curcumin, can solve problems such as weak stability of curcumin

Inactive Publication Date: 2007-07-25
WENZHOU GUANGCHENG BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0018] Through a large number of documents and patents, we found that although it is generally believed that the active groups in the structure of curcumin are its phenolic hydroxyl group and β-diketone group, in curcumin analogues that do not contain these two active groups In terms of research, it has also been found that monocarbonyl curcumin analogues that do not contain β-diketones sometimes show stronger activity, which raises doubts that the β-diketone gr

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  • Analog of mono carbonyl structure of curcumin, and usage
  • Analog of mono carbonyl structure of curcumin, and usage
  • Analog of mono carbonyl structure of curcumin, and usage

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Embodiment Construction

[0080] In the following non-limiting examples, the invention is illustrated in more detail.

[0081] A.Materials and methods

[0082] Preparation of compounds 1, 2, 3, 4, 5, 6, and 8: at room temperature, dissolve 0.01 mol of the corresponding benzene ring substitute in 10 ml of absolute ethanol, slowly add 0.005 mol of dried acetone dropwise, and stir for 10 minutes ; Slowly add 18% methanol solution containing 0.005mol sodium methoxide dropwise, stir and react for 3 to 10 hours, and a yellow precipitate is formed. After the reaction, 50ml of water was added, filtered, the filter residue was washed successively with 50ml of water and 50ml of ethanol, and vacuum-dried at 30°C. The obtained crude product was purified by silica gel column chromatography (methanol:chloroform 1:13).

[0083] Compound 1, yellow powder (56.1% yield), mp122-124°C; 1 HNMR (CDCl 3 , 400MHz) δ (ppm) 1.39 (6H, t, CH 3 ×2), 4.10 (4H, q, O-CH 2×2), 6.99(4H, m, J=7.2, Ar-H), 7.14(2H, d, J=16Hz, CH-C=O×...

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Abstract

This invention relates to curcumin analogs and their applications. Curcumin is an excellent precursor compound, and has multiple pharmaceutical activities. The curcumin analogs in this invention have more stable monocarbonyl intermediate connection chain structure. The connection chain can be acetone, cyclopentanone or cyclohexanone. The substituent on benzene ring can be separately selected from H, hydroxyl, halogen, alkoxyl, alkyl, halogenated alkyl, amino, and alkyl amino. This invention also discloses pharmaceutically acceptable salts of the curcumin analogs, preparations containing them, and their pharmaceutical applications. Experiments show that the curcumin analogs can be used to treat inflammation and tumor.

Description

1. Technical field [0001] The present invention relates to a class of structural analogues of curcumin. Compared with curcumin, the structure of this type of compound only contains a carbonyl group; the present invention also relates to the preparation of such compounds, pharmaceutical preparations and their anti-inflammatory, anti-tumor aspects of use. 2. Background technology [0002] Curcumin is an important active ingredient found in almost all ginger plants. In India, Brazil, the Philippines, Japan, South Korea and other places, there are thousands of years of edible and medicinal records. Curcumin is a compound with strong pharmacological activity and wide indications. In recent years, medicinal chemistry and pharmacology studies have found that curcumin has various pharmacological effects such as anti-inflammation, anti-tumor, anti-angiogenesis, anti-mutation, anti-bacterial, anti-virus, anti-oxidation and neuroprotection. Curcumin has entered phase I in the United ...

Claims

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Application Information

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IPC IPC(8): C07C49/255C07C49/517A61K31/12A61K9/00A61P29/00A61P35/00
Inventor 梁广李校堃杨树林赵昱周慧萍姜丽娟雷培培温红林滨
Owner WENZHOU GUANGCHENG BIOTECH
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