Capsaicin-containing nicotinic acid derivative, preparation method and use thereof

A technology of nicotinic acid esters and compounds, which is applied in the field of capsaicin-containing nicotinic acid capsaicin ester derivatives, preparation and use, can solve the problems of insufficient capsaicin activity, poor water solubility of capsaicin, difficulty in absorbing irritants, etc., and facilitate industrialization Production, appetite-stimulating, and digestion-improving effects

Active Publication Date: 2021-11-23
NANHUA UNIV
View PDF3 Cites 0 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
  • Capsaicin-containing nicotinic acid derivative, preparation method and use thereof
  • Capsaicin-containing nicotinic acid derivative, preparation method and use thereof
  • Capsaicin-containing nicotinic acid derivative, preparation method and use 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 present invention provides a class of nicotinic acid-containing capsaicin derivatives with general structural formula I and a production method thereof, and such derivatives have analgesic, anti-tumor, anti-inflammatory, anti-atherosclerosis, lowering blood fat, promoting Appetite, improving digestion, antibacterial and insecticidal, antioxidative, antiviral purposes.

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
Patent Type & Authority Patents(China)
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 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