Apigenin-7-O-beta-D-glucuronide derivative, and preparation method and application thereof

A technology of scutellarin and its derivatives, which is applied in the preparation of sugar derivatives, sugar derivatives, sugar derivatives, etc., can solve the problems of limiting the application of scutellarin, short oral half-life, poor water solubility and fat solubility, etc. Achieve the effect of high inhibition rate, simple process and high physiological activity

Active Publication Date: 2014-10-08
KPC PHARM INC
View PDF3 Cites 5 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, although scutellarin has significant curative effects in anti-ulcer, anti-senile dementia, anti-reflux esophagitis, etc., due to its special molecular structure, its water solubility and fat solubility are poor, while the solubility of the drug Play a decisive role in the absorption and metabolism of drugs in the body
Therefore, the molecular structure of scutellarin directly determines its low bioavailability and short oral half-life, which seriously limits the application of scutellarin in the field of medicine

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
  • Apigenin-7-O-beta-D-glucuronide derivative, and preparation method and application thereof
  • Apigenin-7-O-beta-D-glucuronide derivative, and preparation method and application thereof
  • Apigenin-7-O-beta-D-glucuronide derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Embodiment 1: the preparation of scutellarin sodium salt (structural compound shown in formula I-a):

[0071] Add 2 g (4 mmol) of scutellarin to a 250 mL round-bottomed flask, and then sequentially add 40 mL of pure water and 40 mL of acetone. Slowly add 1 mol / L sodium hydroxide aqueous solution dropwise under stirring at 0°C until the pH is 8, and the reaction solution continues to stir for half an hour until the reaction is complete. The reaction solution was filtered with a microporous membrane, about 100 mL of acetone was added to the filtrate, and a large amount of precipitation was precipitated. Continue to stir for half an hour and then filter with suction, wash the filter cake with acetone until the filtrate is colorless. The filter cake was collected and dried under reduced pressure at 30° C. to 40° C. to obtain 2 g of orange-red scutellarin sodium salt with a yield of 95% and a chromatographic purity of over 99%.

[0072] 1 HNMR (500MHz, DMSO), δ (ppm): 7.9...

Embodiment 2

[0078] Embodiment 2: the preparation of scutellarin potassium salt (structural compound shown in formula I-b)

[0079] Add 2 g (4 mmol) of scutellarin to a 250 mL round bottom flask, then sequentially add 40 mL of pure water and 20 mL of tetrahydrofuran, and slowly add 2 mol / L potassium hydroxide solution dropwise under stirring at -10°C until the pH is 9. The reaction solution was stirred for half an hour until the reaction was complete. The reaction solution was filtered with a microporous membrane, and about 100 ml of tetrahydrofuran was added to the filtrate, and a large amount of precipitation was precipitated. Continue to stir for half an hour and then filter with suction, wash the filter cake with acetone until the filtrate is colorless. The filter cake was collected and dried under reduced pressure at 30-40°C to obtain 2.1 g of orange-yellow scutellarin potassium salt with a yield of 96% and a chromatographic purity of over 99%.

[0080] 1 HNMR (500MHz, DMSO), δ (pp...

Embodiment 3

[0086] Embodiment 3: the preparation of scutellarin lithium salt (structural compound shown in formula I-c)

[0087] Add 2 g (4 mmol) of scutellarin to a 250 mL round-bottomed flask, and then sequentially add 40 mL of pure water and 80 mL of acetonitrile. Under magnetic stirring at 30°C, slowly add 3 mol / L lithium hydroxide aqueous solution dropwise until the pH is 8.5, and continue stirring for half an hour until the reaction is complete. The reaction solution was filtered with a microporous membrane, and about 100 ml of acetonitrile was added to the filtrate, and a large amount of precipitation was precipitated. Continue to stir for half an hour and then filter with suction, wash the filter cake with acetone until the filtrate is colorless. The filter cake was collected and dried under reduced pressure at 30-40° C. to obtain 1.9 g of orange-yellow scutellarin lithium salt with a yield of 95% and a chromatographic purity of over 99%.

[0088] 1 HNMR (500MHz, DMSO), δ (ppm)...

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 relates to the technical field of pharmaceutical chemistry, and especially relates to an apigenin-7-O-beta-D-glucuronide derivative, and a preparation method and application thereof. The provided apigenin-7-O-beta-D-glucuronide derivative has the structure shown as the formula I, and is relatively high in water solubility, and thus the characteristic that apigenin-7-O-beta-D-glucuronide is not easy to dissolve in water is changed. The provided preparation method comprises: taking apigenin-7-O-beta-D-glucuronide as a raw material, and using an inorganic-base or organic-base reaction to generate the provided apigenin-7-O-beta-D-glucuronide derivative. The preparation method is simple and easily practicable in technology. Experiments show that the provided apigenin-7-O-beta-D-glucuronide derivative has high inhibition rate on aldose reductase compared with apigenin-7-O-beta-D-glucuronide, and the apigenin-7-O-beta-D-glucuronide derivative prepared by employing the preparation method has the purity larger than 99% and the yield larger than 79%.

Description

technical field [0001] The invention relates to the technical field of medicinal chemistry, in particular to scutellarin derivatives and their preparation methods and uses. Background technique [0002] 5,4'-dihydroxyflavone-7-O-D-glucuronic acid, also known as apigenin-7-O-β-D-glucuronide, is derived from the plant Asteraceae breviscapita (also known as breviscapine) A flavonoid glycoside compound extracted from [Erigeron breviscapus (Vant.) Hand-Mazz], scutellarin has a structure as shown in formula I, and is distributed in various natural medicinal plants (such as: breviscapus , Kudiezi, Dimograss, mulberry leaves, stinky sycamore leaves, daisies, etc.). [0003] [0004] Taking male Wistar rats as objects, the effect of breviscapine on kainate-induced senile dementia induced by kainic acid damage, β-amyloid-induced senile dementia, and vascular dementia induced by middle cerebral artery infarction (MCAO) was verified. Therapeutic effect. The pathological results sh...

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): C07H17/07C07H1/00A61K31/352A61P3/10A61P25/00A61P1/00A61P25/28A61P27/02A61P17/02
Inventor 李鹏辉张伟杨兆祥张志朋王珺
Owner KPC PHARM INC
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

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

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap