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

Nicotinic acid-containing capsaicin ester derivative, preparation method and application thereof

A technology of nicotinic acid esters and compounds, which is applied in the field of nicotinic acid-containing capsaicin ester derivatives, preparation and application, and can solve the problems of low absorption, insufficient capsaicin activity, and low bioavailability

Active Publication Date: 2018-05-25
NANHUA UNIV
View PDF3 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Capsaicin has a good analgesic effect, but due to the poor water solubility of capsaicin, it is difficult to absorb and irritating when taken orally, which limits its application
In addition, further studies have found that the activity of capsaicin in the body is not high enough, the absorption is small, the metabolism is fast, and the bioavailability is low, which further limits its application.

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
  • Nicotinic acid-containing capsaicin ester derivative, preparation method and application thereof
  • Nicotinic acid-containing capsaicin ester derivative, preparation method and application thereof
  • Nicotinic acid-containing capsaicin ester derivative, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] 8-methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (compound 1, code 1) and 8-methyl- Preparation of N-[(4-hydroxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (compound 2, code 2):

[0083]0.1mol 8-methyl-N-[(3,4-dihydroxyphenyl)-methyl]-(trans)-6-nonenylamide was mixed with 0.15mol in 100ml of thionyl chloride at 80°C Nicotinic acid was reacted for 10 hours, poured into an ice-water bath, extracted 3 times with ethyl acetate, dried over anhydrous sodium sulfate, and then column chromatographed with ethyl acetate:petroleum ether=1:2~1:5 to obtain the target product 8 -Methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide, yield 48.8%; and 8-methyl-N-[ (4-Hydroxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide, yield 44.3%. The relevant data are as follows:

[0084] 8-Methyl-N-[(3-hydroxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (Compound 1) MS(EI,70ev)m / z: 370; Anal. Calcd. for C21H26O4N2: C, 68.21, H...

Embodiment 2

[0088] Preparation of 8-methyl-N-[(3-methoxy-4-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (compound 3):

[0089] Dissolve 0.2mol of methyl iodide and 0.1mol of 8-methyl-N-[(3-methoxy-4-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide in 300ml of acetone , add 12 grams of catalyst K2CO3, and react with 0.15mol nicotinic acid at 80°C for 3 hours to obtain the target product 8-methyl-N-[(3-methoxy-4-nicotinate phenyl)-methyl]- (trans)-6-Nonenylamide. The relevant data are as follows:

[0090] MS (EI, 70ev) m / z: 384; Anal. Calcd. for C22H28O4N2: C, 68.75, H, 7.29, N 7.29; Found C, 68.70, H, 7.25, N 7.24.

Embodiment 3

[0092] Preparation of 8-methyl-N-[(4-methoxy-3-nicotinate phenyl)-methyl]-(trans)-6-nonenylamide (Compound 4)

[0093] According to the operation of Example 2, just use 8-methyl-N-[(4-methoxy-3-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide instead of 8-methyl -N-[(3-methoxy-4-hydroxyphenyl)-methyl]-(trans)-6-nonenylamide to give the compound 8-methyl-N-[(4-methoxy- 3-Nicotinate phenyl)-methyl]-(trans)-6-nonenylamide. The relevant data are as follows:

[0094] MS (EI, 70ev) m / z: 384; Anal. Calcd. for C22H28O4N2: C, 68.75, H, 7.29, N 7.29; Found C, 68.70, H, 7.25, N 7.24.

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 a nicotinic acid-containing capsaicin ester derivative with a general structural formula I and a preparation method thereof. The derivative has analgesic, anti-tumor, anti-inflammatory, anti-atherosclerosis, hypolipidemic, appetite promoting, digestion improving, antibacterial and insecticide, anti-oxidant, anti-viral applications.

Description

technical field [0001] The invention relates to a class of capsaicin-containing nicotinic acid derivatives and a manufacturing method thereof, and such derivatives have the functions of analgesia, anti-tumor, anti-inflammation, anti-atherosclerosis, lowering blood fat, promoting appetite, improving digestion, antibacterial and antibacterial properties. Insect, anti-oxidant, anti-viral purposes. Background technique [0002] Capsaicin is a main active ingredient in the spicy ingredients of capsicum fruit. At present, this kind of substance has been widely used as an additive in the chemical industry and in the pharmaceutical industry. Capsaicin has various pharmacological activities such as analgesia, anti-tumor, anti-inflammation, anti-atherosclerosis, lowering blood lipid, promoting appetite, improving digestion, antibacterial and insecticidal, anti-oxidation, anti-viral and selective for neurotransmitters and pharmacological effects. Capsaicin has a good analgesic effect...

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): C07D213/80C07D213/803A61K31/455A61P29/00A61P35/00A61P9/10A61P3/06A61P1/14A61P31/00A61P31/12
CPCC07D213/80C07D213/803
Inventor 郑兴姚旭向梦辉杨泽华陈洪飞龙进刘倬李书婷
Owner NANHUA 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