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

Andrographolide derivative and preparation method and application thereof

A technology of andrographolide and derivatives, applied in the directions of drug combination, metabolic diseases, antibacterial drugs, etc., can solve problems such as indirect causes of antitumor activity, and achieve obvious effect and hypoglycemic effect.

Inactive Publication Date: 2012-07-18
JINAN UNIVERSITY
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Andrographolide also increases the production of TNF-α and the expression of CD4 markers leading to the toxicity of lymphocytes to tumor cells, which may be the indirect cause of its antitumor 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
  • Andrographolide derivative and preparation method and application thereof
  • Andrographolide derivative and preparation method and application thereof
  • Andrographolide derivative and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0066] Synthesis of Example 1 Compound 2

[0067] Andrographolide 1 (150mg, 0.43mmol) was dissolved in 2,2-dimethoxypropane (0.2ml, 0.85mmol), pyridinium p-toluenesulfonate (3mg, 0.88mmol) and toluene / DMSO (3ml / 0.4ml) of the mixed solution, stirred at 80°C for 1 hour, after the reaction was complete, cooled to room temperature, and the reaction mixture was terminated with triethylamine (0.1ml). The reaction mixture was diluted with toluene (20ml), washed with water (15ml), and the organic layer was washed with anhydrous Na 2 SO 4 After drying and concentration, the resulting white solid was washed with ether and filtered to obtain compound 2 (130 mg, 78%).

Embodiment 2

[0068] Example 2 Synthesis of compound AC-002 (synthetic route diagram as figure 1 shown)

[0069] Ethyl chloroformate (0.33ml, 3.4mmol) was added to 5-cyclopentylpentanoic acid (350mg, 2.0mmol) CH 2 Cl 2 (16ml) solution, add 0.63mL of triethylamine, and stir in an ice-water bath under nitrogen protection for 1h. Compound 2 (200 mg, 0.5 mmol) was dissolved in CH 2 Cl 2 (20ml), was added dropwise to the mixture, and stirred at room temperature for 40h. Add CH after reaction 2 Cl 2 (50ml) diluted with NaHCO 3 Aqueous solution and water wash. Anhydrous NaSO for organic layer 4 Dry and concentrate in vacuo. The mixture was separated on a silica gel column (PE:EA=2:1) ​​to obtain compound AC-001 as a colorless viscous liquid (132 mg, 47.6%).

[0070] Compound AC-001 was added to acidic aqueous solution (AcOH / H 2 O=7 / 3, 10ml), stirred at room temperature within 30min. The reaction mixture was added with water and NaHCO 3 , with a large amount of CH 2 Cl 2 extraction....

Embodiment 3

[0073] Embodiment 3. the synthesis of compound AC-004 (synthetic route figure such as figure 1 shown)

[0074] Ethyl chloroformate (0.33ml, 3.4mmol) was added to 3-furanoacrylic acid (283mg, 2.0mmol) CH 2 Cl 2 (16ml) solution, add 0.63mL of triethylamine, and stir in an ice-water bath under nitrogen protection for 1h. Compound 2 (200 mg, 0.5 mmol) was dissolved in CH 2 Cl 2 (20ml), was added dropwise to the mixture, and stirred at room temperature for 40h. Add CH after reaction 2 Cl 2 (50ml) diluted with NaHCO 3 Aqueous solution and water wash. Anhydrous NaSO for organic layer 4 Dry and concentrate in vacuo. The mixture was separated on a silica gel column (PE:EA=2:1) ​​to obtain compound AC-003 as a colorless viscous liquid (112.3 mg, 43%).

[0075] Compound AC-003 was added to acidic aqueous solution (AcOH / H 2 O=7 / 3, 10ml), stirred at room temperature within 30min. The reaction mixture was added with water and NaHCO 3 , with a large amount of CH 2 Cl 2 extrac...

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 discloses an andrographolide derivative and a preparation method and application thereof. The derivative has a structure expressed by the formula (1), wherein R1 is C1 to C11 chain hydrocarbon or C1 to C11 chain hydrocarbon with terminals substituted by ternary to heptabasic ring groups; and R2 and R3 are hydrogen, organic acid radical, inorganic acid radical, alkyl or acryl. The andrographolide derivative can be made into tablets, capsules, granules, fine granules, powder, pills, patches, oral liquid or injection.

Description

technical field [0001] The invention belongs to the technical field of traditional Chinese medicines, and in particular relates to an andrographolide derivative and a preparation method and application thereof. Background technique [0002] Andrographolide (Andro) is one of the main active ingredients in Andrographis paniculata of the Acanthaceae plant, which has antipyretic and anti-inflammatory effects, including rheumatoid arthritis, pharyngitis, diarrhea, bacterial and viral infections. Recently, studies have shown that andrographolide has broad-spectrum anticancer effects, and the therapeutic effect is good. In India and Malaysia, andrographolide is widely used in the treatment of diabetes. In the past 30 years, andrographolide has been widely used clinically in China. [0003] [0004] A study of the antibacterial activity of andrographolide. Andrographis paniculata extract was used to treat acute upper respiratory tract infection combined with sinusitis. The res...

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): C07D307/60A61K31/365A61P35/00A61P29/00A61P3/10A61P31/04A61P31/12
Inventor 王玉强于沛张高小徐立朋王中利曾祥萍
Owner JINAN UNIVERSITY
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