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A kind of curcumol derivative with antitumor activity and its preparation method and application

An anti-tumor activity, curcumitol technology, applied in the field of medicine, can solve the problems of limited application and clinical use, low curcumitol, enhanced immunogenicity, etc., to facilitate formulation development and clinical application, enhance water solubility, and improve bioavailability. Effect

Active Publication Date: 2018-11-30
同写意(北京)科技发展有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] Curcumol (Curcumol), as an antitumor drug discovered in recent years, its mechanism of action includes inhibiting angiogenesis, inhibiting nucleic acid metabolism, affecting cell differentiation, inducing apoptosis, directly killing tumor cells, and enhancing immunogenicity; Tumors have been tested in vitro, and have achieved certain curative effects, which have good development and utilization value, but the solubility of curcumol in water is very low, even if a cosolvent is added, the solubility can only be close to 0.5%, which has become an influence on its anti-inflammatory effect. One of the important factors of tumor activity also limits its good application and clinical application. In view of the limitation of chemically variable sites in its structure, so far there are few reports on its structural modification by organic chemical methods

Method used

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  • A kind of curcumol derivative with antitumor activity and its preparation method and application
  • A kind of curcumol derivative with antitumor activity and its preparation method and application
  • A kind of curcumol derivative with antitumor activity and its preparation method and application

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Effect test

Embodiment 1

[0028] Embodiment 1: the preparation of curcumol derivative

[0029] (1) Preparation Scheme 1

[0030] Compound 1a Compound 2a For example, the synthetic route 1 is as follows:

[0031]

preparation approach 1

[0033] (1) Take 4.72g of curcumol, dissolve it in 80mL of dry tetrahydrofuran, add 1.2g (60%) of sodium hydride, heat to reflux for 2h, cool, add 2.93g of ethyl chloroacetate, and continue to reflux for 14h. After the reaction is complete, concentrate, add 100 mL of water, extract 3 times with ethyl acetate, combine the ethyl acetate layers, backwash the ethyl acetate layer with saturated sodium chloride aqueous solution, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure to obtain a brown oily product , a colorless oily product 1a was obtained by silica gel column chromatography.

[0034] (2) Take 1.61g of 1a, dissolve it in a mixed solution of 24mL ethanol and 8mL water, add 0.63g of lithium hydroxide monohydrate, and stir at room temperature for 4h. Remove ethanol by rotary evaporation, add appropriate amount of water, adjust pH to 5-6 with 10% hydrochloric acid, extract 3 times with ethyl acetate, combine ethyl acetate layer, backwash ethyl acetat...

preparation approach 2

[0039] (1) Take 2.48g of 4-methylpiperidine, dissolve it in 20mL of dry tetrahydrofuran solution, add 7.59g of triethylamine, and slowly add 10mL of tetrahydrofuran containing 4.24g of chloroacetyl chloride dropwise under stirring at room temperature, for 1h After the dropwise addition, continue to react for 2 h at room temperature. After the reaction is complete, concentrate, add 40 mL of water, extract 3 times with ethyl acetate, combine the ethyl acetate layers, backwash the ethyl acetate layer with a saturated sodium chloride aqueous solution, and anhydrous Dried over magnesium sulfate, concentrated under reduced pressure to obtain a tan crude product, dried in a vacuum oven, and directly put into the next reaction.

[0040] (2) Take 1.18 g of curcumol, dissolve it in 20 mL of dry tetrahydrofuran solution, add 0.3 g of sodium hydride, heat and reflux for 2 hours, let it cool slightly, add 1.05 g of the compound obtained in the previous step (1), and continue heating and ref...

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PUM

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Abstract

The invention relates to curcumol derivatives with anti-tumor activity, and a preparation method and application of the curcumol derivatives, belonging to the technical field of medicines. The invention relates to new compounds which have the anti-tumor activity and are as shown in a general formula I. The invention also relates to preparation and use of the compounds. A series of curcumol derivatives with the anti-tumor activity are designed and synthesized by taking an easily obtained natural product, i.e., curcumol as a raw material and using a partial synthesis method, and the curcumol derivatives show the better anti-tumor activity in in-vitro experiments; the compounds can be applied to the research of anti-tumor medicines by means of further experiments. (The general formula I is shown in the description.).

Description

technical field [0001] The invention belongs to the field of medicine, and specifically relates to a curcumol derivative, a preparation method of the compound, a composition containing the compound and the application of the compound in pharmacy, especially in the preparation of antitumor drugs. Background technique [0002] Tumor is second only to cardiovascular disease in terms of mortality, and is now the most serious disease that endangers human life. The study of tumor has always been one of the key contents of medicine. For tumor diseases, the current Western medicine clinical treatment methods commonly used surgical resection, radiotherapy, chemotherapy and so on. Although the curative effect is relatively fast, radiotherapy and chemotherapy also have a greater killing effect on normal cells while killing tumor cells; and the anti-tumor drugs synthesized by Western medicine are expensive, bringing greater pain and unbearable pain to patients. economic burden. my cou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D493/08A61K31/352A61K31/453A61K31/496A61K31/4025A61P35/00
CPCC07D493/08
Inventor 陈立江赵京华刘举王欣
Owner 同写意(北京)科技发展有限公司
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