Looking for breakthrough ideas for innovation challenges? Try Patsnap Eureka!

Preparation method and application of sphaelactone

A technology of lactone and parthenolide, applied in the field of medicine, can solve the problems of many side reactions, flammability of boron trifluoride, high toxicity and the like

Active Publication Date: 2013-12-11
ACCENDATECH +1
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method and application of sphaelactone
  • Preparation method and application of sphaelactone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: Preparation of laughing lactones

[0027] At room temperature, 500 mg of parthenolide and 34 mg of 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. Wash with 200 mL of 5% sodium bicarbonate and 300 mL of saturated brine, then dry with anhydrous sodium sulfate, and concentrate under reduced pressure to obtain a crude product containing laugholide, which is then subjected to silica gel column chromatography (petroleum ether:ethyl acetate=80:20 ) to obtain 300 mg of laughter, the yield is 60%.

[0028] The spectral data of the prepared laugholide are as follows:

[0029] 1 H NMR (CDCl 3 , 400MHz)δ6.14(d, J=3.2Hz, 1H), 5.45(d, J=2.8Hz, 1H), 3.76(t, J=10.4Hz, 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...

Embodiment 2

[0031] Example 2: Pharmacological effects of laughing lactones

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

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

[0034]

[0035] The results of the activity test showed that the killing rate of laugholide on leukemia stem cells was comparable to that of the posi...

Embodiment 3

[0040] Example 3: Injection containing laugholide

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The present invention relates to a preparation method of mimilactone and its application. The preparation method uses parthenolide as a raw material, an appropriate acid as a catalyst, and a certain solvent and reaction temperature to obtain mimilactone of the present invention; The present invention also provides the medicinal application of mimilactone, and the application of the pharmaceutical composition containing therapeutically effective dose of mimilactone and a pharmaceutically acceptable carrier in the preparation of medicines for treating cancer. The preparation method of the present invention solves the technical defect of low production rate of micinolactone, so that the yield of micinolactone reaches more than 60%, and the effect of micinolactone in treating leukemia is almost equal to that of parthenolide, and It has no obvious killing effect on normal cells.

Description

technical field [0001] The present invention belongs to the technical field of medicine, and specifically, the present invention relates to a preparation method of laurolactone, a pharmaceutical composition for treating cancer or adjuvant treatment of tumors using the medicine as an active ingredient, and uses thereof, as well as the medicinal compound and Application of the composition in the preparation of anticancer or auxiliary anticancer drugs. Background technique [0002] Tumors are a great threat to human health. There are about 2 million cancer patients in my country, and 1.6 million new cases are diagnosed every year. This is a large group. Anti-tumor research is a very challenging and significant field in the field of life sciences today. . In the past, the treatment methods focused on the eradication and killing of cancer cells. At present, the commonly used anti-tumor drugs in clinical practice are mainly cytotoxic drugs. , is a typical double-edged drug, and i...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Patents(China)
IPC IPC(8): C07D307/93A61K31/365A61P35/00A61P35/02
CPCA61P35/00A61P35/02C07D307/93
Inventor 陈悦张泉翟佳黛马维维范洪霞张福武
Owner ACCENDATECH
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Patsnap Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Patsnap Eureka Blog
Learn More
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com