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Curcumenol derivative as well as preparation method and application thereof in antitumor drugs

A technology of curcumol and derivatives, applied in the field of medicine, can solve the problems of difficult preparation research, low bioavailability, low water solubility, etc., and achieve the effects of improving drug efficacy, good antitumor activity, and increasing water solubility

Active Publication Date: 2017-05-10
科贝源(北京)生物医药科技有限公司
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AI Technical Summary

Problems solved by technology

[0007] Although curcumol has anti-tumor activity, its water solubility is low, the solubility at room temperature is only 0.3%, it is difficult to carry out preparation research, and its bioavailability is not high, thus limiting its clinical application, so it is necessary to study its structure modification

Method used

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  • Curcumenol derivative as well as preparation method and application thereof in antitumor drugs
  • Curcumenol derivative as well as preparation method and application thereof in antitumor drugs
  • Curcumenol derivative as well as preparation method and application thereof in antitumor drugs

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Embodiment 1

[0027] Embodiment 1: the synthesis of curcumol derivative

[0028]

[0029] The general preparation method takes the synthesis of compound BD-1 as an example:

[0030] Take 1.18g (5mmol) of curcumol, dissolve it in 30mL dry tetrahydrofuran solution, add 0.30g (7.5mmol, 60%) of sodium hydride, heat and reflux at 66-73°C for 1h, let cool slightly, add 2-( Chloromethyl)imidazo[1,2-a]pyridine 1.00g (6mmol), continue to heat up, reflux at 66-73°C for 10h, and monitor the reaction by TLC. After the reaction is complete, remove most of the reaction solvent tetrahydrofuran by rotary evaporation, add 30mL of water, extract 3 times with 40mL of ethyl acetate, combine the ethyl acetate layers, backwash the ethyl acetate layer with saturated sodium chloride aqueous solution, anhydrous magnesium sulfate The ethyl acetate layer was dried appropriately, filtered after 1 h, and concentrated under reduced pressure to obtain a tan oily product, which was further purified by silica gel colum...

Embodiment 2

[0036] In vitro anticancer activity research of embodiment 2 curcumol derivatives:

[0037] MTT method is used to determine the drug concentration when the inhibitory rate of curcumol derivatives to human cervical cancer cell line HeLa cell, human liver cancer cell line HepG2 cell line and human lung cancer cell line A549 cell reaches 50%.

[0038] Tumor cells in the logarithmic growth phase were selected, digested with trypsin, and mixed with RPMI 1640 medium to make 6×10 4 / mL of the cell suspension, and then the cell suspension was added to a 96-well culture plate and cultured for 24 hours at 37°C and 5% CO2. Add the pre-configured drugs with different concentration gradients to the 96-well cell culture plate, set up 3 parallel wells for each concentration gradient, 37°C, 5% CO 2 After culturing for 24 hours under the same conditions, discard the supernatant, wash twice with PBS, add 10 μL of newly prepared MTT medium to each well, continue culturing at 37°C for 4 hours, d...

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Abstract

The invention discloses a curcumenol derivative as well as a preparation method and application thereof in antitumor drugs. The curcumenol derivative disclosed by the invention has a structure of a general formula (I). The curcumenol derivative with antitumor activity disclosed by the invention takes a chemical structure of curcumenol as a basis, introduces different nitrogen-containing substituent groups, has the effects of inhibiting the activities of human cervical carcinoma cells, human liver cancer cells and human lung cancer cells and has high antitumor activity. The structural formula is shown in the specification.

Description

technical field [0001] The invention relates to the technical field of medicine, more specifically to derivatives of curcumol, methods for preparing derivatives of curcumol and applications of derivatives of curcumol. The method is to modify the structure of curcumol monomer with anti-tumor activity to obtain a series of curcumol derivatives with better curative effect. [0002] technical background [0003] Anti-tumor, as a hot spot in the medical circle of the present era, has always attracted countless medical workers to explore and study. At present, the use of traditional Chinese medicine extracts to treat tumors has made gratifying progress in the experimental treatment of tumors, and its development prospects are relatively optimistic. Studies have found that Chinese medicine monomers have similar effects as co-stimulatory molecules. Using Chinese medicine monomers to carry out a series of biological constructions on tumor cells may effectively stimulate the body's an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08C07D519/00A61K31/519A61K31/437A61K31/4433A61P35/00
CPCC07D493/08C07D519/00
Inventor 陈立江赵京华刘举刘宇
Owner 科贝源(北京)生物医药科技有限公司
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