Curcumin derivative and application of curcumin derivative as cannabinoid receptor modulator

A technology of curcumin derivatives and curcumin, which is applied in the direction of drug combination, active ingredients of heterocyclic compounds, digestive system, etc., can solve the problems of limited application, less absorption, and excessive metabolism, and achieve the effect of reducing deposition and promoting degradation

Inactive Publication Date: 2013-12-18
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
View PDF4 Cites 2 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, further studies have found that curcumin has low activity in the body, less absorption in the body, fast metabolism, and low bioavailability, which greatly limits its application.
Howev

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 derivative and application of curcumin derivative as cannabinoid receptor modulator
  • Curcumin derivative and application of curcumin derivative as cannabinoid receptor modulator
  • Curcumin derivative and application of curcumin derivative as cannabinoid receptor modulator

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0020] Example 1: Synthetic process of tetrahydrocurcumin derivatives

[0021] On the basis of summarizing the synthetic methods of curcumin-related analogues, the following synthetic routes were designed to synthesize the target compounds.

[0022]

[0023] Wherein R1 and R2 are each a pyrrole ring or a similar structure.

example 2

[0024] Example 2: Curcumin derivatives inhibit the occurrence and development of liver fibrosis

Embodiment 1

[0025] Example 1: Curcumin protects liver damage and inhibits CCL 4 Induces hepatic fibrogenesis in rat liver tissue.

[0026] 1. Experimental materials

[0027]1.1 Experimental animals

[0028] Several SPF grade male SD rats (Shanghai Slack Company, SCXK (Shanghai) 2012-0015).

[0029] 1.2 Experimental drugs

[0030] Curcumin derivatives (prepared and synthesized in laboratory, content ≥99.8%)

[0031] 1.3 Experimental reagents

[0032] CCl 4 (domestic analytically pure) mixed with olive oil (Shandong Luhua Co., Ltd.) 1:1 to make 50% CCl 4 Organic solvent for modeling; BCA kit (PIERCE); primary antibody collagen and Fibronectin (Epitomics), β-actin (Sigma); sodium pentobarbital (Shanghai Chemical Reagent Company); absolute ethanol (AR, Nanjing Chemical Reagent Co., Ltd.); formaldehyde (AR, Shanghai Chemical Reagent Company); reagents used in Western Blot experiments: 1.5M Tris-HCl, 1M Tris-HCl, 30% acrylamide solution, TBST, Running buffer, Transfer buffer, 5% skimmed ...

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 preparation of a curcumin derivative and application of the curcumin derivative as a cannabinoid receptor modulator. In the synthetic route of the curcumin derivative, 10% of Pd-C is used for reducing the curcumin; for protecting a phenolic hydroxyl group, only 2.0% mol of DMAP (Dimethylaminopyridine) is used for catalysis and (Boc)2O of which the mole amount is 2.05 times as much as that of the curcumin is used so that reaction is completely realized; during a Mannich reaction, Mannich reagents such as N,N,N',N'-tetramethyldiaminomethane prepared in advance are used so as to avoid that an acid component reacts with formaldehyde to generate by-products at first. In the whole route, the target compound is obtained through reducing, protection, alkylation, deprotection and the Mannich reaction with the curcumin as the raw material. The route has the characteristics of cheap and available raw material, high yield and easy operation. The curcumin derivative is capable of inhibiting the hepatic stellate cells of a hepatic fibrosis rat from synthesizing and secreting extracellular matrix through a cannabinoid receptor, promoting the degradation of the extracellular matrix, reducing the deposition of the extracellular matrix in the liver and further developing the effect of treating the hepatic fibrosis.

Description

technical field [0001] The invention relates to the preparation of curcumin derivatives and their application as cannabinoid receptor modulators, in particular to the effect of curcumin derivatives in the preparation of anti-fibrosis drugs. technical background [0002] Hepatic fibrosis (Hepatic Fibrosis, HF) is a compensatory response in the tissue repair process secondary to various forms of chronic liver injury, and it is also a necessary pathological process for the development of chronic liver disease to cirrhosis. Hepatic stellate cells (HSCs) are the main source of extracellular matrix proteins in chronic liver diseases. When liver fibrosis occurs, HSCs are abnormally activated and proliferated, and synthesize and secrete a large amount of extracellular matrix (Extracellular matrix, ECM), which eventually leads to excessive deposition of ECM. During liver injury, HSC undergo a phenotypic shift, acquiring myofibroblast characteristics, increased collagen synthesis and...

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): C07D295/112A61K31/40A61P1/16
Inventor 郑仕中孔德松张峰张自力张衍张射郭瑶倪雯霞王妤清
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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