Cyclopentanone-containing curcumin monocarbonyl structural analogues and application thereof

A technology of compounds and pharmaceutical preparations, applied in the field of structural analogs of curcumin, which can solve problems such as weak stability of curcumin

Inactive Publication Date: 2012-05-02
WENZHOU GUANGCHENG BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0019] 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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  • Cyclopentanone-containing curcumin monocarbonyl structural analogues and application thereof
  • Cyclopentanone-containing curcumin monocarbonyl structural analogues and application thereof
  • Cyclopentanone-containing curcumin monocarbonyl structural analogues and application thereof

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Embodiment Construction

[0082] In the following non-limiting examples, the invention is illustrated in more detail.

[0083] A.Materials and methods

[0084] 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).

[0085]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

The invention relates to curcumin structural analogues and application thereof. Curcumin is an excellent lead compound and has a plurality of pharmacological activity. Compared to curcumin, the analogues provided in the invention have a more stable monocarbonyl intermediate joining chain, and the joining chain is cyclopentanone; substituents on a phenyl ring of the analogues have a specific combination. The invention also includes pharmaceutically acceptable salts of the analogues, medicinal preparations containing the analogues and application of the analogues in pharmacy. According to results of related research, the analogues can be used for treating inflammation and tumors.

Description

[0001] The present invention is a divisional application of Chinese Patent Application No. 200710066787.1. 1. Technical field [0002] 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 [0003] 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...

Claims

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Application Information

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IPC IPC(8): C07C49/753C07C49/697C07C49/683C07C225/22C07D309/12C07C217/22A61K31/122A61K31/136A61K31/351A61K31/138A61P29/00A61P35/00
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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