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

Andrographolide phosphoric acid derivatives and preparation method thereof

A technology of andrographolide and andrographolide, applied in the field of andrographolide phosphoric acid derivatives and its preparation, can solve the problems of unsatisfactory solubility, low bioavailability, and large irritation, and achieve good antiviral infection effect

Inactive Publication Date: 2012-04-04
JIANGXI HERBFINE HI TECH
View PDF1 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the solubility of the above-mentioned known medicines in water is not ideal, the bioavailability is low, and the irritation is large

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 phosphoric acid derivatives and preparation method thereof
  • Andrographolide phosphoric acid derivatives and preparation method thereof
  • Andrographolide phosphoric acid derivatives and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Embodiment 1, the preparation method of andrographolide phosphorus oxychloride:

[0024] 20g of dehydroandrographolide was dissolved in 80ml of pyridine and cooled. Add POCl dropwise at 0°C 3 30g (dissolved in 50ml chloroform), then reacted for 0.5h, with saturated Na 2 CO 3 , water were washed separately, anhydrous MgSO 4 Drying, draining, and ethanol recrystallization gave 18 g of colorless dehydroandrographolide phosphorus oxychloride with a yield of 90%.

[0025]

Embodiment 2

[0026] Embodiment 2, the preparation method of andrographolide phosphorus oxychloride:

[0027] Dissolve 10g of andrographolide in 40ml of pyridine, add 120ml of chloroform at the same time, and cool with cold salt. At -5°C, POCl was added dropwise 3 / CHCl 3 liquid (containing POCl 3 18g), reaction 1h, with saturated Na 2 CO 3 , water were washed separately, anhydrous MgSO 4 Drying, vacuuming, and recrystallization from methanol gave 9 g of colorless andrographolide phosphorus oxychloride with a yield of 90%.

Embodiment 3

[0028] Embodiment 3, the preparation method of andrographolide phosphoric acid:

[0029] Dissolve 35g (0.1mol) of andrographolide in 150ml of pyridine, cool, and at -10°C, add POCl dropwise at a controlled rate 3 65g (0.4mol), stirred at 0°C for 0.5h, added saturated Na 2 CO 3 The pH of the solution was adjusted to 7 (at this time, the temperature was controlled at 3°C). And a small amount of acetone to dissolve the flocculent precipitate, then stir and hydrolyze for 40h at 20°C.

[0030] The organic phase was extracted three times with 60 ml of chloroform, the aqueous layer was adjusted to pH=3 with hydrochloric acid, the precipitate was completely precipitated, and suction filtered to obtain 29.7 g of andrographolide phosphate as a light blue solid (yield 85%)

[0031]

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 andrographolide phosphoric acid derivatives and a preparation method thereof. The andrographolide phosphoric acid derivatives has a chemical structural formula shown in the specification, wherein W is N or O, X is C1-C8 linear-chain group, heterocyclic radical, nitrogen mustard group, phenyl, benzyl or furfuryl. According to the preparation method, andrographolide phosphorus oxychloride, andrographolide phosphoric acid, andrographolide phosphorus diethylamide and andrographolide benzyl phosphate are respectively prepared from andrographolide serving as a raw material. The derivatives prepared by the method have excellent effects of resisting virus infection, diminishing inflammation and resisting bacteria, resisting cancers and cardiovascular diseases, stimulating immunity.

Description

technical field [0001] The invention relates to a preparation method of an antibacterial and anti-inflammatory drug, in particular to a phosphoric acid derivative of andrographolide and a preparation method thereof. Background technique [0002] Andrographis paniculata (Burm.f.) Nees is the whole grass or leaf of the Acanthaceae plant Andrographis paniculata (Burm.f.) Nees. Also known as spring lotus and autumn willow, happy at first sight, elemi, bitter gall grass, golden vanilla, golden ear hook, Indian grass, bitter grass and so on. It has the effects of clearing away heat and detoxification, reducing inflammation, reducing swelling and relieving pain. In order to improve the curative effect, after extracting andrographolide, various injections of water-soluble derivatives are prepared, such as "Lianbizhi", "Chuanhuning", and "Xiyanping". However, the above-mentioned known medicines have unsatisfactory solubility in water, low bioavailability, and high irritation. Con...

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 Applications(China)
IPC IPC(8): C07F9/6574
Inventor 杨世林简晖李少华范玫玫孙勇兵陈兰英李俊
Owner JIANGXI HERBFINE HI TECH
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