Curcumenol derivative containing triazole structure and application thereof in preparation of medicine for treating human colorectal cancer

A technology of triazole and curcumol, which is applied in the field of natural medicine and medicinal chemistry, can solve the problems of low anti-tumor activity and low water solubility, and achieve good biological activity, easy availability of raw materials, and low production cost

Active Publication Date: 2020-05-15
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, due to the unique chemical structure of curcumol, its water solubility is low, the ant

Method used

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  • Curcumenol derivative containing triazole structure and application thereof in preparation of medicine for treating human colorectal cancer
  • Curcumenol derivative containing triazole structure and application thereof in preparation of medicine for treating human colorectal cancer
  • Curcumenol derivative containing triazole structure and application thereof in preparation of medicine for treating human colorectal cancer

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0053] Example 1: Synthesis of Curcumol Derivative C-01 Containing Aryltriazole Structure

[0054]

[0055] Take 5.0g (21.15mmol) of curcumol, dissolve it in 50mL of dichloromethane, and add 7.30g (42.31mmol) of m-CPBA (m-chloroperoxybenzoic acid) in batches under the condition of ice-water bath. Stir at room temperature 25°C for 3h, check the reaction by TLC until the reaction is complete, concentrate the reaction solution, add saturated sodium bicarbonate to remove residual m-chloroperoxybenzoic acid, extract with ethyl acetate, combine the ethyl acetate phase, and saturated chlorine The ethyl acetate layer was washed three times with sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain compound 1-1 (4.87 g) as a light yellow oily product with a yield of 91.22%.

[0056] Take 2.0g (7.93mmol) of compound 1-1, dissolve it in 20mL of ethanol, heat to 70°C and stir, add 0.17g (4.25mmol) of sodium hydroxide, heat to r...

Embodiment 2

[0059] Example 2: Synthesis of Curcumol Derivative C-02 Containing Aryltriazole Structure

[0060]

[0061] Take 5.0g (21.15mmol) of curcumol, dissolve it in 50mL of dichloromethane, and add 7.30g (42.31mmol) of m-CPBA (m-chloroperoxybenzoic acid) in batches under the condition of ice-water bath. Stir at room temperature 25°C for 3h, check the reaction by TLC until the reaction is complete, concentrate the reaction solution, add saturated sodium bicarbonate to remove residual m-chloroperoxybenzoic acid, extract with ethyl acetate, combine the ethyl acetate phase, and saturated chlorine The ethyl acetate layer was washed three times with sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain compound 1-1 (4.87 g) as a light yellow oily product with a yield of 91.22%.

[0062] Take 2.0g (7.93mmol) of compound 1-1, dissolve it in 20mL of ethanol, heat to 70°C and stir, add 0.17g (4.25mmol) of sodium hydroxide, heat to r...

Embodiment 3

[0065] Example 3: Synthesis of Curcumol Derivative C-03 Containing Aryltriazole Structure

[0066]

[0067] Take 5.0g (21.15mmol) of curcumol, dissolve it in 50mL of dichloromethane, and add 7.30g (42.31mmol) of m-CPBA (m-chloroperoxybenzoic acid) in batches under the condition of ice-water bath. Stir at room temperature 25°C for 3h, check the reaction by TLC until the reaction is complete, concentrate the reaction solution, add saturated sodium bicarbonate to remove residual m-chloroperoxybenzoic acid, extract with ethyl acetate, combine the ethyl acetate phase, and saturated chlorine The ethyl acetate layer was washed three times with sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain compound 1-1 (4.87 g) as a light yellow oily product with a yield of 91.22%.

[0068] Take 2.0g (7.93mmol) of compound 1-1, dissolve it in 20mL of ethanol, heat to 70°C and stir, add 0.17g (4.25mmol) of sodium hydroxide, heat to r...

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Abstract

The invention discloses an aryl triazole curcumenol derivative shown as a formula (I) and an application of the aryl triazole curcumenol derivative in the preparation of a medicine for treating humancolorectal cancer. According to the invention, a curcumenol 12-site double bond structure is modified; a plurality of curcumenol derivatives containing a triazole structure are obtained; an in-vitro cell experiment shows that the curcumenol derivative containing a triazole structure has good biological activity on a human colon cancer Sw620 cell strain, which can be used for preparing the curcumenol derivative containing a triazole structure and can be used to prepare a medicine for treating human colorectal cancer. The curcumenol derivative can prevent or/and treat human colorectal cancer, and has a huge application prospect in the field of medicine. The synthesis method of the curcumenol derivative containing a triazole structure is simple and convenient, mild in reaction conditions, andeasy to operate, moreover, the raw materials are easily available, the production cost is low, and the curcumenol derivative is suitable for industrial production and application.

Description

technical field [0001] The invention belongs to the field of natural medicine and medicinal chemistry, in particular to a curcumol derivative containing an aryl triazole structure and its application, in particular to a curcumol derivative containing a triazole structure and its use in the preparation and treatment of human Drug use in colorectal cancer. Background technique [0002] Colorectal cancer (carcinoma of colon and rectum) is a common malignant tumor in the gastrointestinal tract, and its morbidity and mortality are second only to gastric cancer, esophageal cancer and primary liver cancer among digestive system malignant tumors. With the improvement of urban modernization, improvement of people's living standards, changes in lifestyle and dietary structure, increased intake of high-calorie, high-fat, and high-protein foods such as chicken, duck, and fish, and the aging of the population, the problem of high incidence of colorectal tumors will increase. It is becom...

Claims

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Application Information

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IPC IPC(8): C07D493/10A61K31/4192A61P35/00
CPCA61P35/00C07D493/10
Inventor 孟祥伟聂添情张兴贤
Owner ZHEJIANG UNIV OF TECH
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