Theasapogenol derivative with anti-tumour activity and preparing method and application thereof

A technology of anti-tumor activity and thea-sapogenin, which is applied in the field of medicine, can solve the problems that the anti-tumor activity of thea-sapogenin and its derivatives has not been reported, and achieve the effect of convenient industrial production, high product purity and high anti-tumor activity

Inactive Publication Date: 2012-08-22
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report about the antitumor activity of thea saponin and its derivatives

Method used

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  • Theasapogenol derivative with anti-tumour activity and preparing method and application thereof
  • Theasapogenol derivative with anti-tumour activity and preparing method and application thereof
  • Theasapogenol derivative with anti-tumour activity and preparing method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] (1) Get tea presapogenol-A crystal (5g, about 8.9mmol) and 50mlDMF (dimethylformamide), stir and dissolve; add triphenylchloromethane (2.5g) reaction under the protection of argon, Then slowly add DMAP (1.2 g about 10 mmol) to catalyze the reaction, and react at 60° C. for 2 hours. After the reaction was completed, the mixture was diluted with water, and ethyl acetate was added for extraction. The organic phase was dried with anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain the crude product a1 with a conversion rate of 98%. The crude product was used in the next reaction without purification.

[0031] (2) Mix a1 (7.0g, about 8.7mmol), tetrabutylammonium iodide (0.4g, 1.1mmol) and tetrahydrofuran (50 mL), and add sodium hydroxide (0.4g, 17.4mmol) under stirring. After about 20 minutes, benzyl bromide (44 mL about 35 mmol) was added to the reaction system, and heated to reflux for 2 h. The reaction mixture was distilled off under r...

Embodiment 2

[0042] (1) Mix 2g (about 2.3mmol) of a2 and 20ml of 1.2-dichloromethane, stir to dissolve, add 0.2ml (0.0029mol) of azide in benzene, cool to -15°C in an ice-salt bath, stir and drop Add a mixed solution containing 0.5 ml of boron trifluoride in ether and 0.5 ml of dichloromethane, keeping the reaction temperature below -15°C. After the dropwise addition, the reaction was stirred at -15°C for 1 hour, and the reaction was checked by TLC for completeness. Add 0.2ml of pyridine to decompose unreacted boron trifluoride, a precipitate is formed, add 10ml of water and stir to dissolve the precipitate, separate the organic layer, wash with 5ml of 5% hydrochloric acid solution and water (10ml×3), anhydrous sodium sulfate After drying, the solvent was evaporated to dryness, and recrystallized with about 50 ml of acetone-methanol (1:1) to obtain white crystal b1.

[0043](2) Add b1 to a 250ml autoclave, add 20ml of dry ethyl acetate to dissolve, add 0.3g of 10% palladium / carbon catalys...

Embodiment 3

[0052] (1) Take a2 (2g, about 2.3mmol), 4-carboxy-2,2,6,6-tetramethylpiperidine nitroxide radical (0.1g), dicyclohexylcarbodiimide (0.1g) Add 50ml of dichloromethane to dissolve, electromagnetically stir for 6h, and detect the end point of the reaction by TLC. Concentrate the solvent under reduced pressure, then use petroleum ether: acetone as the developing solvent, and prepare through a thin layer of silica gel GF254 to obtain compound c1.

[0053] (2) After c1 was dissolved in ethanol (100ml), 10% Pd / C (1g) was added, 1 atmosphere of hydrogen gas was introduced, and the mixture was refluxed at room temperature for 12h. The mixture was filtered to remove insoluble matter, and the residue after distilling off ethanol from the filtrate under reduced pressure was extracted with ethyl acetate, and the extract was washed with water and saturated sodium chloride, respectively. The organic phase was separated and dried over anhydrous magnesium sulfate. The desiccant was removed b...

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Abstract

The present invention discloses a theasapogenol derivative with anti-tumour activity and preparing method and application thereof. The theasapogenol derivative with anti-tumour activity has a structure shown as formula I; and the preparing method comprises the following steps of: (1) reacting theasapogenol, which is the raw material, with trityl chloride in a pyridine solvent by using 4-dimethylamino pyridine as a catalyst, reacting the reaction product with benzyl bromide, and reacting the product thereof with formic acid to obtain alcohol terpenoid compound; (2) introducing in methylsulfonyl at C-28 bit based on the alcohol terpenoid compound; introducing in cyano at the C-28 bit with NaCN as a cyaniding reagent; and finally removing benzyl at palladium / carbon under hydrogen reduction condition, so as to obtain the theasapogenol derivative with anti-tumour activity shown as formula I. The theasapogenol derivative of the present invention has high anti-tumour activity; the preparing method and process are simple; and the theasapogenol derivative is convenient for industrial production.

Description

technical field [0001] The invention relates to the field of medicine, in particular to teasapogenin derivatives with antitumor activity, a preparation method and application thereof. Background technique [0002] Malignant tumors are the second most lethal disease after cardiovascular and cerebrovascular diseases. Although early surgical treatment can be curative, most patients are already in the middle and advanced stages when they are discovered, and the possibility of surgical cure is small. Drug therapy is still the most important treatment for cancer patients. Chemotherapy has always been the mainstay of tumor treatment, but chemotherapy will bring serious adverse reactions, such as bone marrow suppression, hair loss, liver and kidney damage, etc. While inhibiting tumor cells, normal cells and tissues are also severely damaged. [0003] Traditional Chinese medicine is becoming more and more important in tumor treatment. Traditional Chinese medicine not only plays a ro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00C07J75/00A61K31/58A61K31/56A61P35/00
Inventor 叶勇王延芳
Owner SOUTH CHINA UNIV OF TECH
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