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

Hydroxylated polymethoxylated flavone and preparation method thereof

A polymethoxyl flavonoid, hydroxylation technology, applied in the direction of organic chemistry, drug combination, antineoplastic drugs, etc., can solve the problem that the anti-liver cancer activity has not been reported in the literature, and achieve simple preparation method, good anti-proliferation activity, good The effect of pro-apoptotic effect

Pending Publication Date: 2021-05-25
WUYI UNIV
View PDF1 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently, OH-PMFs have little literature report on their anti-hepatocarcinoma activity

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
  • Hydroxylated polymethoxylated flavone and preparation method thereof
  • Hydroxylated polymethoxylated flavone and preparation method thereof
  • Hydroxylated polymethoxylated flavone and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] This embodiment provides the synthesis method of the synthesis of target product 5-DMN, and the synthetic reaction of target product 5-DMN is as follows:

[0032] Dissolve 1 mmol of nobiletin in 25 mL of anhydrous acetonitrile, add 8 mmol of anhydrous aluminum chloride, stir at 60° C. for 3 h, and detect the end point of the reaction by TLC.

[0033] Add 20mL of 3% hydrochloric acid solution, continue stirring for 0.5h, then cool the reaction solution to room temperature, extract with ethyl acetate (3×20mL), anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel chromatography (eluent: n-hexane: ethyl acetate = 2:1), recrystallized from ethanol, and dried in vacuo to obtain the target product 5-DMN with a yield of about 56%.

[0034] The synthesis process is as follows:

[0035]

[0036] Target product 5-DMN: yellow solid powder. 1 H NMR (500MHz, DMSO-d...

Embodiment 2

[0038] This example provides the synthesis method of the target compound 5,3'-DMN

[0039] The synthesis process of the target compound 5,3'-DMN is as follows;

[0040]

[0041] Dissolve 1mmol of 3'-hydroxy-5,6,7,8,4'-pentamethoxyflavone in 25mL of anhydrous acetonitrile, add 8mmol of anhydrous aluminum chloride, stir at 60°C for 3h, TLC Detection of reaction endpoints.

[0042] Add 20mL of 3% hydrochloric acid solution, continue stirring for 0.5h, then cool the reaction solution to room temperature, extract with ethyl acetate (3×20mL), anhydrous Na 2 SO 4 After drying, the solvent was removed under reduced pressure to obtain a crude product. The crude product was separated and purified by silica gel column chromatography (eluent: n-hexane: ethyl acetate = 2:1), recrystallized from ethanol, and dried in vacuo to obtain the target product 5,3'-DMN with a yield of about 47%.

[0043] Target product 5,3'-DMN: yellow solid powder. 1 H NMR (500MHz, DMSO-d 6 )δ12.74(s,1H),9...

Embodiment 3

[0045] This example provides the synthesis method of compound 5,4'-DMN, specifically as follows:

[0046] Dissolve 1mmol of 4'-hydroxy-5,6,7,8,3'-pentamethoxyflavone in 25mL of anhydrous acetonitrile, add 8mmol of anhydrous aluminum chloride, stir at 60°C for 3h, TLC Detection of reaction endpoints.

[0047] Add 20 mL of 3% hydrochloric acid solution, continue stirring for 0.5 h, then cool the reaction solution to room temperature, extract with ethyl acetate (3×20 mL), dry over anhydrous Na2SO4, and remove the solvent under reduced pressure to obtain a crude product.

[0048] The crude product was separated and purified by silica gel chromatography (eluent: n-hexane: ethyl acetate = 2:1), recrystallized from ethanol, and dried in vacuo to obtain the target product 5,4'-DMN with a yield of about 60%.

[0049] The synthesis process is as follows:

[0050]

[0051] Target product 5,4'-DMN: yellow solid powder. 1 H NMR (500MHz, DMSO-d 6 )δ12.77(s,1H),10.06(s,1H),7.58(s,2H),7....

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 invention provides hydroxylated polymethoxylated flavone and a preparation method thereof. The chemical structure of a compound is shown as a formula (I). The method comprises the following steps: synthesizing an intermediate product 2a by using an intermediate product 1a, dissolving the intermediate product 2a in anhydrous acetonitrile, adding anhydrous aluminum chloride, adding a hydrochloric acid solution, cooling a reaction solution to room temperature, conducting extracting with ethyl acetate, carrying out drying with anhydrous Na2SO4, removing a solvent under reduced pressure to obtain a crude product, separating and purifying the crude product with a silica gel chromatographic column, conducting recrystallizing with ethanol, and carrying out drying in vacuum to obtain a target product 3a. According to the invention, four compounds prepared in the invention are subjected to anti-proliferative activity screening, cell cycle capture experiments and cell apoptosis experiments of liver cancer cell HepG2, and the results show that the four compounds have good anti-proliferative activity and apoptosis promoting effect on HepG2 cells.

Description

technical field [0001] The invention relates to the technical field of synthesis of new drug compounds, in particular to a hydroxylated polymethoxy flavone, a preparation method and application. Background technique [0002] Polymethoxylated flavonoids (PMFs) are a class of compounds with strong biological activity, low polarity and planar structure. Rutaceae citrus plants are the main source of PMFs, which are contained in Chinese medicinal materials such as green peel, orange peel, and orange red. PMFs have various pharmacological effects such as anti-inflammation, anti-cancer, anti-oxidation and prevention of cardiovascular and cerebrovascular diseases. [0003] Hydroxylated polymethoxylated flavones (OH-PMFs) are the products of the conversion of methoxy groups in PMFs to hydroxyl groups. Compared with the corresponding PMFs, hydroxylated polymethoxylated flavones have stronger antioxidant, free radical scavenging and tumor inhibiting activities. [0004] Therefore, O...

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
IPC IPC(8): C07D311/30A61P35/00
CPCC07D311/30A61P35/00
Inventor 辛燕萍黄庆荣李冬利郑婷张瑞强
Owner WUYI UNIV
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