Eureka AIR delivers breakthrough ideas for toughest innovation challenges, trusted by R&D personnel around the world.

Curcumin-4-nitrogen-containing derivatives, and preparation method and uses thereof

A technology of curcumin and its derivatives, which is applied in the fields of antibacterial multifunctional dyes and photosensitive materials, and curcumin-4-nitrogen-containing derivatives, which can solve the problems of curcumin's poor water solubility, easy oxidation, and low curcumin absorption rate, etc. question

Inactive Publication Date: 2012-08-15
LESHAN NORMAL UNIV
View PDF4 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Also because of the low molecular weight and low toxicity of curcumin, it is considered to be very safe and one of the ideal chemotherapeutic drugs. However, in new research, it was found that curcumin has poor water solubility and is easily oxidized in vitro. Oral administration of curcumin The absorption rate of the hormone is very low, and most of it is metabolized in the gastrointestinal tract, so its bioavailability in the body is low

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
  • Curcumin-4-nitrogen-containing derivatives, and preparation method and uses thereof
  • Curcumin-4-nitrogen-containing derivatives, and preparation method and uses thereof
  • Curcumin-4-nitrogen-containing derivatives, and preparation method and uses thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Preparation of Compound 1

[0029] Dissolve 3mmol curcumin in 20mL tetrahydrofuran, after cooling to 0~5 ℃, dropwise add 16.5% (weight percent) 7mmol sodium nitrite aqueous solution 3mL, 37% (weight percent) concentrated hydrochloric acid 1mL successively, then in ice-water bath The reaction was stirred for 2 to 6 hours, and the reaction was detected by TLC. After the reaction was completed, most of the solvent was distilled off under reduced pressure, 30 mL of water was added to the residue, and the pH was adjusted to 6 to 7 with 10% (weight percent) aqueous sodium bicarbonate solution. Suction filtration, washing with water, and vacuum drying to obtain the crude product, which was separated and purified by silica gel column chromatography (eluent: methanol: chloroform = 1: 10-8, volume ratio) to obtain compound 1 (purity over 98%).

[0030] Compound 11,7-bis(4-hydroxy-3-methoxy)phenyl-4-hydroxyimino-1,6-heptadiene-3,5-dione (common name: curcumin-4-oxime)

...

Embodiment 2

[0033] Example 2 Preparation of Compound 2

[0034] Get 3mmol two-O-acetyl curcumin and be dissolved in 30mL tetrahydrofuran, after cooling to 0~5 ℃, drip 7mmol sodium nitrite aqueous solution 3mL of 16.5% (weight percent) successively, and 37% (weight percent) concentrated 1 mL of hydrochloric acid was then stirred in an ice-water bath for 2 to 8 hours, and the reaction was detected by TLC. After the reaction was completed, most of the solvent was distilled off under reduced pressure, 30 mL of water was added to the residue, and 10% (weight percent) sodium bicarbonate was used. The pH of the aqueous solution was adjusted to 6-7, filtered with suction, washed with water, and dried in vacuo to obtain the crude product, which was separated and purified by silica gel column chromatography (eluent: methanol:chloroform=1:10-8, volume ratio) to obtain compound 2 ( more than 98% purity).

[0035] Compound 2 1,7-bis(4-acetoxy-3-methoxy)phenyl-4-hydroxyimino-1,6-heptadiene-3,5-dione (...

Embodiment 3

[0038] Example 3 Preparation of compound 3

[0039] Add 2.4 mmol of piperidine to 20 mL of tetrahydrofuran (THF), add concentrated hydrochloric acid dropwise in an ice-water bath to adjust the pH to 6, dropwise add 2.4 mmol of formaldehyde, introduce a stream of nitrogen, and slowly add 20 mL of 20 mL of curcumin dissolved in 0 to 5°C dropwise. The tetrahydrofuran solution was continuously stirred for 4-10 h. The reaction was detected by TLC, the solvent was recovered after the reaction, and the 10% (weight percent) aqueous sodium bicarbonate solution was neutralized to pH 6~7, and the crude product was isolated and obtained, which was subjected to silica gel column chromatography (eluent: methanol: chloroform=1: 12~8 , volume ratio) separation and purification to obtain compound 3 (purity above 98%).

[0040] Compound 3 1,7-bis(4-hydroxy-3-methoxy)phenyl-4-(N-piperidinylmethyl)-1,6-heptadiene-3,5-dione

[0041]

[0042] Khaki powder (43.8% yield), mp 185-187°C; IR (KBr) ...

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

A curcumin-4-nitrogen-containing derivatives or pharmaceutically acceptable salt thereof is shown as the formula (I) or the formula (II): the compound shown as the formula (I) is the derivative obtained by introducing oximino to 4-position methylene, wherein, when R1 is hydrogen, alkyl or halogenated alkyl, R2 is hydrogen, alkyl or acyl; the compound shown as the formula (II) is the derivative obtained by Mannich reaction on the 4-position methylene, wherein, when R3 is hydrogen, alkyl or acyl, R4 is hydrogen, alkyl or aryl, R5 is alkyl amino, halogenated alkyl amino, morpholinyl or N-alkyl hexahydropyrazine. The main uses thereof are reflected in being used as photosensitive material and antibiotic multifunctional dyes, in being used as bactericide or pesticide for agriculture or animals, and in being used for sterilization, anti-inflammation, antitumor, cancer prevention, anticancer, anti-HIV and hypolipemic.

Description

technical field [0001] The present invention relates to a class of structural analogs of curcumin, in particular to curcumin-4-nitrogen-containing derivatives and their salts, their preparation methods and their use in antibacterial multifunctional dyes and photosensitive materials, agricultural and veterinary applications Sterilization and insecticidal, medicinal sterilization, anti-inflammatory and anti-tumor uses. Background technique [0002] Turmeric has been used for thousands of years as a traditional medicine. It is mainly used to treat internal and external trauma, liver disease (especially jaundice), detoxification, joint pain (rheumatoid arthritis), etc. Curcumin [1,7-bis(4-hydroxy-3-methoxy)phenyl-1,6-heptadiene-3,5-dione] is the main component of traditional Chinese medicine turmeric. Curcumin is also a food coloring. Studies have found that it has a wide range of biological activities, such as antioxidant, anticancer, hypolipidemic, antibacterial and inhibiti...

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): C07C251/40C07D295/104C09B57/00A01N37/14A01N43/40A01P3/00A01P7/00A61K31/222A61K31/4453A61P31/00A61P29/00A61P35/00A61P31/18A61P3/06
Inventor 刘志昌王应红向清祥
Owner LESHAN NORMAL 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
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