Preparation method of curcumin derivatives, and antitumor drug

A technology of curcumin derivatives and curcumin, which is applied in the direction of antineoplastic drugs, drug combinations, medical preparations containing active ingredients, etc., can solve the problems of curcumin's poor water solubility, low bioavailability, and fast metabolism in the body, and achieve Good water solubility, high bioavailability, and slow metabolism in the body

Inactive Publication Date: 2013-10-02
HENAN UNIVERSITY OF TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the embodiments of the present invention is to provide a method for preparing curcumin derivatives, which aims to sol...

Method used

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  • Preparation method of curcumin derivatives, and antitumor drug
  • Preparation method of curcumin derivatives, and antitumor drug
  • Preparation method of curcumin derivatives, and antitumor drug

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0054] Example 1 Synthesis of 4-(2-furyl methylene) curcumin.

[0055] Weigh 1.0g (2.72mmol) of curcumin and dissolve it in a mixed solution of methanol-chloroform (methanol 29ml, chloroform 13ml), and add dropwise 0.2ml of hexahydropyridine as a catalyst, and add dropwise a methanol solution of furfuraldehyde (wherein Furfural 0.23ml, about 0.26g, furan formaldehyde redistilled before use), reacted at room temperature for 48h, let the reactant stand still, filtered out the precipitated product (keep the mother liquor), and washed 4 times with 20ml petroleum ether to remove unreacted Raw materials, after drying the product, 0.25g of yellow powder was obtained.

[0056] Concentrate the above mother liquor to about 10ml, wash the reaction solution with water to precipitate the product from the reaction solution, filter the obtained precipitate, wash with 20ml of petroleum ether for 4 times, filter and dry to obtain 0.68g of the product. The products obtained above were combined...

Embodiment 2

[0059] The synthesis of embodiment two p-carboxyphenylhydrazine curcumin

[0060] Weigh 1.0g (2.72mmol) of curcumin and dissolve it in 35ml of glacial acetic acid, add 0.45g (3.48mmol) of p-carboxyphenylhydrazine and heat to reflux at 120°C for 12 hours. After the reaction was finished, the solvent was evaporated under reduced pressure to obtain a brownish-red oily product, which was poured into a 150ml beaker equipped with crushed ice cubes, and the product was turned into powder under constant stirring, then suction filtered and dried. The product was recrystallized with ethanol:ethyl acetate (5:2), dried in vacuum to constant weight, and weighed 0.85g.

[0061] The product is an orange powder with a yield of 64.4% and a melting point of 157-159°C.

[0062] UV-Vis: λmax (EtOH) 332nm, 429nm. IR(KBr):3381cm -1 (ν OH ),3015cm -1 (ν =CH2 ),2937cm -1 (ν CH2 ),1699cm -1 (ν C=O ),1604cm -1 (ν C=N ),1031cm -1 、1369cm -1 (ν C-H ),792cm -1 、866cm -1 (Meta-substituted ...

Embodiment 3

[0063] The detection of embodiment three compound antitumor activity in vitro

[0064] The tumor cell line used is the human lung cancer A549 cell line. The A549 cells in the logarithmic growth phase were planted in a 96-well plate. After growing to the logarithmic growth phase, drug treatment was added. The control group was added with a certain volume of DMSO, and the experimental group was added with different concentrations of drugs. , placed in an incubator for different periods of time, 4 hours before the end of the drug action time, add 20 μl of MTT stock solution to each well of each group, and place it in the incubator in the dark to continue culturing, discard the supernatant of each well after 4 hours, Add 100 μl DMSO respectively, shake on a shaker at 37°C for 15 minutes, then measure the OD value of each well at 490 nm with a microplate reader, and calculate the cell survival rate: survival rate = (OD experimental group / OD control group) × 100%, activity inhibition...

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Abstract

The invention discloses a preparation method of curcumin derivatives, and an antitumor drug. The preparation method comprises the steps of: weighing curcumin to be dissolved into methanol-chloroform mixture solution, and dropwise adding hexahydropyridine as a catalyst; dropwise adding furan formaldehyde methanol solution under stirring, reacting at room temperature, and standing; filtering to retain precipitation product, washing with petroleum ether to remove unreacted active ingredients, and drying; concentrating the filtered mother liquor, washing the reaction liquid with water, separating out the product, filtering to obtain precipitation, washing with petroleum ether, filtering and drying; combining to obtain the product, placing the chloroform-methanol mixture solution for recrystalization, and drying the product to be constant-weight. The new curcumin derivatives synthesized by structure improvement of two curcumin derivatives: 4-(2-fural) curcumin and hydrazinobenzoic acid curcumin which are synthesized by adopting the preparation method of curcumin derivatives is good in water solubility, slow in in-vivo metabolism, high in bioavailability, and higher in activity, and has important application prospects.

Description

technical field [0001] The invention belongs to the field of preparation of curcumin derivatives, in particular to a preparation method of curcumin derivatives and its application in the preparation of antitumor drugs. Background technique [0002] Curcumin is a natural active ingredient extracted from the rhizomes of turmeric, zedoary, and turmeric, which are plants of the genus Curcumagenus in the ginger family. [0003] Curcumin is the most important active ingredient in the genus Curcuma longa that exerts pharmacological effects, and its structural formula is shown in the figure. [0004] [0005] It has been proved that curcumin and some of its analogues have anti-tumor, anti-inflammatory, anti-tumor, anti-oxidation, anti-hepatotoxicity, anti-rheumatism, antibacterial, anti-Alzheimer's disease, lowering cholesterol and other extensive pharmacological effects. However, curcumin also has disadvantages such as poor water solubility, fast metabolism in vivo, low bioavai...

Claims

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Application Information

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IPC IPC(8): C07D307/46C07D231/12A61K31/341A61K31/415A61P35/00
Inventor 孙纲春周广舟李志成游利琴谢晶曦李俊海
Owner HENAN UNIVERSITY OF TECHNOLOGY
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