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Cyclohexanone-contained mono-carbonyl analogues of curcumin and usage thereof

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

Inactive Publication Date: 2012-03-21
WENZHOU GUANGCHENG BIOTECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 group is an essential group for the activity of curcumin
Moreover, due to the existence of the β-diketone structure, the stability of curcumin is weak, and it has better stability only when PH<6.5
[0020] It can be seen that the structure-activity relationship of curcumin may not be as simple as the current research, and drug screening using curcumin as a lead should not be completely based on the premise of retaining the phenolic hydroxyl group and diketone structure

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  • Cyclohexanone-contained mono-carbonyl analogues of curcumin and usage thereof
  • Cyclohexanone-contained mono-carbonyl analogues of curcumin and usage thereof
  • Cyclohexanone-contained mono-carbonyl analogues of curcumin and usage 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), mp 122-124°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 cyclohexanone-contained mono-carbonyl analogues of curcumin and usage thereof. When compared with curcumin which is an excellent lead compound and has various pharmacological activities, the analogues have more stable mono-carbonyl intermediate junction chain structure, cyclohexanone serves as the joint chain, and substituent on benzene rings of the analogues has specificcombination. Pharmaceutically acceptable salts of the analogues, pharmaceutical preparations contained the analogues and pharmaceutical usages of the analogues are further provided. Correlational researches of the cyclohexanone-contained mono-carbonyl analogues of curcumin show that the analogues can be used for treatment of 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07C49/225C07C49/235C07C49/217C07C49/248C07C49/753C07C49/747C07C49/697C07C49/683C07C45/74C07C225/22C07C221/00C07D309/12A61K31/136A61K31/351A61K31/122A61K31/12A61P29/00A61P35/00
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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