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Preparation method and application of sphaelactone

A technology of lactone and parthenolide, which is applied in the field of medicine, can solve the problems of many side effects, strong corrosion, and high toxicity

Active Publication Date: 2011-11-09
ACCENDATECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] Michelactone is a guaiacane-type sesquiterpene lactone compound, reported in the literature [J.Nat.Prod.1993, 56, 90-98; Bioorg.Med.Chem.Lett.2003, 11, 1503-1510] The synthetic method yield is low (13~26%), side reaction is many, and the catalyst used in the reaction is boron trifluoride etherate complex, boron trifluoride is flammable, highly toxic, highly corrosive, and this just Greatly limit the industrial application

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of micolactone

[0027] At room temperature, 500 mg parthenolide and 34 mg p-toluenesulfonic acid were dissolved in 50 mL of toluene, and the reaction was refluxed for 12 hours. The reaction solution was poured into an appropriate amount of ice water, extracted with ethyl acetate, and then the ethyl acetate layers were separated Washed with 200mL of 5% sodium bicarbonate and 300mL of saturated brine, then dried over anhydrous sodium sulfate, concentrated under reduced pressure to obtain the crude product containing sulcolactone, and then used silica gel column chromatography (petroleum ether: ethyl acetate = 80: 20 ) 300 mg of saccharolactone was obtained, and the yield was 60%.

[0028] The spectral data of the prepared micolactone is as follows:

[0029] 1 H NMR(CDCl 3 , 400MHz) δ 6.14 (d, J = 3.2 Hz, 1H), 5.45 (d, J = 2.8 Hz, 1H), 3.76 (t, J = 10.4 Hz, 1H), 2.61-2.68 (m, 3H), 1.98-2.36(m, 6H), 1.67-1.77(m, 2H), 1.62(s, 3H), 1.28(s, 3H); 13 C NMR(CDC...

Embodiment 2

[0031] Example 2: Pharmacological effects of mirin

[0032] 2.1 In vitro cell test: Take cancer cells labeled with leukemia stem cells and make the cells into 2×10 5 / mL cell suspension, add it to the 96-well round-bottom cell culture plate, add parthenolide (positive control) and mirinolide (product prepared in Example 1) to make their concentrations both: 25.0μM, 50.0μM , 5 wells for each test concentration, set at 37℃, 5% CO 2 Incubate for 18 hours under saturated humidity conditions, and measure the absorbance (A) value with an enzyme-linked detector at 570nm wavelength by MTT method. The inhibitory effect of the compound of the present invention on leukemia cells was calculated.

[0033] Table 1 Survival rate of cancer stem cells and normal cells (%) after adding sinolactone

[0034]

[0035] The results of the activity test showed that the killing rate of micolactone on leukemia stem cells was equivalent to that of the positive control drug parthenolide, and micolactone had no...

Embodiment 3

[0040] Example 3: Injection containing laughing lactone

[0041] The mirinolactone prepared in Example 1 was dissolved with a small amount of DMSO, water for injection was added as usual, precision filtered, and potted and sterilized to prepare an injection solution.

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Abstract

The invention relates to a preparation method and an application of sphaelactone; according to the preparation method, the sphaelactone of the invention is obtained by using parthenolide as a raw material, using a proper acid as a catalyst, with a certain solvent and under a certain reaction temperature; the invention also provides a pharmaceutical application of sphaelactone, that is, the application of a pharmaceutical composition containing a treatment-effective dose of sphaelactone and a pharmaceutically acceptable carrier in the preparation of medicaments for treating cancers. The preparation method of the present invention solves the technical defect of low preparation yield of sphaelactone, provides a sphaelactone yield of up to above 60%; and the sphaelactone has almost identical effect with parthenolide in treating leukemia, and has no obvious killing effect on normal cells.

Description

Technical field [0001] The present invention belongs to the technical field of medicines. Specifically, the present invention relates to a preparation method of sinolactone and a pharmaceutical composition for treating cancer or adjuvant treatment of tumors using the medicine as an active ingredient and its use, as well as the pharmaceutical compound and Application of the composition in preparing anticancer or auxiliary anticancer drugs. Background technique [0002] Tumors are a great threat to human health. There are currently about 2 million cancer patients in my country, and 1.6 million new cases occur every year. This is a large group. Anti-tumor research is a challenging and significant field in the field of life sciences today. . In the past, treatment methods focused on eradicating and killing cancer cells. At present, the most commonly used anti-tumor drugs in clinical practice are mainly cytotoxic drugs. Such anti-cancer drugs have disadvantages such as poor selectivit...

Claims

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Application Information

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IPC IPC(8): C07D307/93A61K31/365A61P35/00A61P35/02
CPCC07D307/93A61P35/00A61P35/02
Inventor 陈悦张泉翟佳黛马维维范洪霞张福武
Owner ACCENDATECH
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