Curcumin analogue and its preparation and application

A technology of curcumin analogues and medicinal salts, which is applied in the application of antineoplastic drugs, intermediates for synthesizing the curcumin analogues and their preparation fields, can solve the problems of low water solubility, poor stability, rapid metabolism, etc. Achieve the effect of improving activity and selectivity

Active Publication Date: 2017-12-15
SHENYANG PHARMA UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, curcumin also has defects such as low water solubility, poor stability, and rapid metabolism in the body.

Method used

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  • Curcumin analogue and its preparation and application
  • Curcumin analogue and its preparation and application
  • Curcumin analogue and its preparation and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 Preparation of 1-(3,4-dimethoxyphenyl)-3,5-diketone-1-hexene (A1)

[0044] Acetylacetone (16.3 mL, 160 mmol) and diboron trioxide (7.8 g, 112 mmol) were added to 100 mL of ethyl acetate, and the temperature was raised to 70° C. for 0.5 h. 3,4-Dimethoxybenzaldehyde (13.2g, 80mmol) and tri-n-butyl borate (21.6mL, 80mmol) were added slowly, and reacted at 70°C for 0.5h. Add 10 mL of ethyl acetate to 8 mL of n-butylamine, and dropwise complete. Reaction at 100°C for 1.5h. Cool down to 60°C, add 50mL of 0.4mol L -1 Hydrochloric acid, reaction 0.5h. After the reaction was completed, cool to room temperature, wash with water, extract the aqueous layer with ethyl acetate (30 mL×3), combine the organic phases, wash with saturated sodium chloride solution, and dry over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained oil was separated and purified by column chromatography (eluent was petroleum ether-ethyl acetate). 6...

Embodiment 2

[0045] Example 2 1-(3,4-dimethoxyphenyl)-7-(3-methoxy-4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (A2 ) preparation

[0046] 6-(3,4-dimethoxyphenyl)hex-5-ene-2,4-dione (10.0 g, 40.3 mmol) (A1) and diboron trioxide (4.8 g, 68.5 mmol) were added Into 160 mL of ethyl acetate, the temperature was raised to 70° C. for 0.5 h. Add 3-methoxy-4-hydroxybenzaldehyde (6.1g, 40.3mmol) and tri-n-butyl borate (18.4g, 79.0mmol) slowly, and react at 70°C for 0.5h. Piperidine (4mL, 40.5mmol) was added dropwise, and after the drop was completed, the temperature was raised to 100°C and reacted for 1.5h. Then cool down to 60°C, add 80mL of 0.4mol·L -1 Hydrochloric acid, reacted for 0.5h, after the reaction was completed, cooled to room temperature, washed with water, extracted the aqueous layer with ethyl acetate (30mL×3), combined the organic phases, washed with saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure...

Embodiment 3

[0047] Example 3 1-(3,4-dimethoxyphenyl)-7-(3-methoxy-4-acetoxyphenyl)-1,6-heptadiene-3,5-dione Preparation of (A3)

[0048] 1-(3,4-dimethoxyphenyl)-7-(3-methoxy-4-hydroxyphenyl)-1,6-heptadiene-3,5-dione (A2) ( 5.0g, 13.1mmol), acetic anhydride (3.0mL, 32.8mmol) and pyridine (2.6mL, 32.8mmol) were added to 50mL of dichloromethane, and refluxed for 5h. After the reaction was completed, it was cooled to room temperature, adjusted to neutral pH with saturated aqueous sodium bicarbonate solution, and dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, a yellow solid was obtained, which was recrystallized from ethyl acetate and petroleum ether to obtain 4.8 g of a yellow solid, with a yield of 86.4%. m.p.133-136℃, ESI-MS, m / z: 425.2[M+H] + .

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Abstract

The invention belongs to the field of medical technology, and relates to the preparation and application of a series of curcumin analogues, which have structures such as formula I, formula II and formula III, wherein R, R1 and R2 are as described in the specification. The pharmaceutically acceptable salts and solvates of the curcumin analogues, as well as the medicines containing the curcumin analogues or pharmaceutically acceptable salts thereof as active ingredients, can be used for treating cancer. The curcumin analogs and their medicinal salts described in the invention have good anticancer activity, and the preparation method is simple, feasible and easy to operate.

Description

Technical field: [0001] The invention relates to a new curcumin analogue and a preparation method thereof, and also relates to an intermediate for synthesizing the curcumin analogue, a preparation method thereof and an application as an antitumor drug. Background technique: [0002] Turmeric is a perennial herb of the genus Curcuma longa. It is recorded in "Compendium of Materia Medica" that turmeric is named Baodingxiang, and its smell is pungent, bitter, severe cold, and non-toxic. It is used for the treatment of unbearable heartache and abdominal pain due to fetal cold. Curcumin is the most important active ingredient of turmeric to exert pharmacological effects and has a wide range of pharmacological effects. Studies have shown that curcumin has obvious inhibitory effects on human gastric cancer, liver cancer, leukemia and other cancers and has little toxic and side effects (Cui Shuxiang, Jin Dongqing, Zhou Ling, etc. Experimental observation of curcumin's anti-tumor ef...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D295/088C07C213/04C07C217/20A61K31/5377A61K31/496A61K31/4545A61K31/4025A61K31/138A61K31/40A61K31/5375A61K31/495A61K31/4453A61P35/00A61P35/02
CPCY02P20/55
Inventor 张美慧曹亮夏明钰徐莉英张平董金华
Owner SHENYANG PHARMA UNIVERSITY
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