Unlock instant, AI-driven research and patent intelligence for your innovation.

Glucose ferulic amide and process for preparing same

A technology of ferulic acid amide and glucose, applied in the field of glucosamide, can solve the problem that derivatives have not been reported, and achieve the effects of promoting drug transdermal penetration activity, high drug transdermal penetration activity, and simple preparation process.

Inactive Publication Date: 2008-10-29
TIANJIN UNIV
View PDF2 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] In summary, glucosamine, ferulic acid and their derivatives have many unique properties, and related novel structural compounds have also been reported from time to time, but derivatives combining the two have not been reported yet

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
  • Glucose ferulic amide and process for preparing same
  • Glucose ferulic amide and process for preparing same
  • Glucose ferulic amide and process for preparing same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1: 2-deoxy-2-(m-methoxy-p-hydroxyphenylacrylamide)-β-D-glucopyranose

[0025] Step 1: Synthesis of N-(β-D-glucose) benzaldimine

[0026] Add glucosamine hydrochloride (46mmol, 10.0g) into an aqueous solution (47mL) containing NaOH (55mmol, 2.2g), and stir until completely dissolved. The solution was cooled down to 0°C, benzaldehyde (53mmol, 5.4mL) was slowly added under vigorous stirring, stirred for 1h and then left at 0°C for 12h. The mixture was then poured into an ice-water mixture and left standing at 0 °C for 1 h. A white precipitate was obtained by filtration, washed with anhydrous ether (60 mL×3), and dried to obtain a white solid (7.9 g, yield 63.7%).

[0027] Step 2: Synthesis of N-(1,3,4,6-tetra-O-acetyl-β-D-glucose) benzaldimine

[0028] Dissolve N-(β-D-glucose)benzaldimine (45mmol, 11.9g) in pyridine (70mL), add acetic anhydride (450mmol, 42mL) under stirring in an ice-water bath, stir in an ice-water bath for 30min, and then heat up Keep warm a...

Embodiment 2

[0035] Example 2: N-(β-D-glucose)-1-(m-methoxy-p-hexadecyloxyphenyl)acrylamide

[0036] Step 1, Step 2, Step 3, and Step 4 of this embodiment are the same as those of Embodiment 1.

[0037] Step 5: 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(m-methoxy-p-hexadecyloxyphenylacrylamide)-β-D-glucopyranose Synthesis

[0038] 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(m-methoxy-p-hydroxyphenylacrylamide)-β-D-glucopyranose (1mmol, 0.523g) Dissolve in N,N-dimethylformamide (10 mL), add sodium hydride (2 mmol, 0.053 g) and hexadecane bromide (1.5 mmol, 0.47 g), and stir at room temperature for 48 h. After evaporating to dryness under reduced pressure, the resulting solid was dissolved in dichloromethane (20 mL), washed with water (30 mL×8), dried over anhydrous sodium sulfate, concentrated, and purified on a silica gel column. The developing solvent is ethyl acetate:petroleum ether=3:2 (V:V). A white solid (0.384 g, yield 51.5%) was obtained. The melting point is 119-121°C. IR(KBr)Δ / cm-1: 3272, 2922...

Embodiment 3

[0041] Example 3: N-(β-D-glucose)-1-(m-methoxy-p-n-octyloxyphenyl)acrylamide

[0042] Step 1: Synthesis of N-(β-D-glucose) benzaldimine

[0043] Add glucosamine hydrochloride (46mmol, 10.0g) into an aqueous solution (47mL) containing NaOH (55mmol, 2.2g), and stir until completely dissolved. The solution was cooled down to 0°C, benzaldehyde (46mmol, 4.7mL) was slowly added under vigorous stirring, stirred for 1h and left at 0°C for 12h. The mixture was then poured into an ice-water mixture and left standing at 0 °C for 1 h. A white precipitate was obtained by filtration, washed with anhydrous ether (60 mL×3), and dried to obtain a white solid (7.3 g, yield 58.8%).

[0044] Step 2: Synthesis of N-(1,3,4,6-tetra-O-acetyl-β-D-glucose) benzaldimine

[0045] Dissolve N-(β-D-glucose)benzaldimine (38mmol, 10.0g) in pyridine (70mL), add acetic anhydride (364mmol, 36mL) under stirring in an ice-water bath, stir in an ice-water bath for 30min, and then heat up Keep warm at 35°C-40°C ...

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

PropertyMeasurementUnit
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
melting pointaaaaaaaaaa
Login to View More

Abstract

The invention discloses a dextrose acidamide ferulate and its process for preparing which belongs to the technique of dextrose amide. The structure of the said dextrose ferulaic acid amide is on the right, in which X stands for hydrogen,paraffin base or alkylene with carbon atoms between one to twenty, or one of paraffin base or alkylene with carbon atoms between one to twenty substituted by alkylamino radical or alkoxy group. Its specific compounds include m-methoxy-p-octane oxophenyl acryloylamino dextrose and so on, which includes: selecting glucosamine as raw materials, by intermediates of glucosschiff bases, glucosschiff bases with proctected hydroxide, glucosamine with proctected hydroxide, 1,3,4,6-tetra-O- acetyl-2-deoxidation-2- (m-methoxy-p-hydroxyphenylacrylamide)- beta-D-glucopyranose and so on, and obtaining the product by hydrolytic decomposition and deprotection. The invention is excellent in that it is of simple process for preparing, the obtained glucosacidamide possesses high acceleration to percutaneous infiltration active of medicines and is nontoxic, nonirritant and allergic reaction to skin, and is suitable for long-term use.

Description

technical field [0001] The invention relates to a glucosylferulic acid amide and a preparation method thereof, belonging to the glucosamide technology. Background technique [0002] D-glucosamine (2-amino-2-deoxy-D-glucose) is an important monosaccharide in the glycoprotein chain of higher animals, which is distributed in human blood, eyeball, cornea, liver, kidney, skin and other tissues, and participates in the structure Human tissues, cell membranes, and interstitial cells not only have anti-inflammatory and stimulating proteoglycan synthesis activities, but also can reduce the production of nitric oxide and prostaglandin E2 in plasma, inhibit platelet aggregation, activate NK and LAK cells, stimulate Bifidobacterium proliferates in the intestinal tract of infants and has immunoregulatory effects. It is now used as a functional raw material for health food; it can be used as an antibacterial and anti-inflammatory drug in medicine for the treatment of rheumatoid arthritis ...

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): C07H15/18C07H1/00
Inventor 周雪琴刘东志姚康德迟玮
Owner TIANJIN UNIV