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

Sterol derivative, and preparation method and application thereof

A technology of sterol derivatives and compounds, applied in the fields of application, steroids, food science, etc., can solve the problems of unreported research on drugs for promoting wound healing, high cholesterol activity, and low toxicity.

Active Publication Date: 2017-06-06
CHINA PHARM UNIV
View PDF2 Cites 9 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Between β-sitosterol, β-stigmasterol, high cholesterol activity, low toxicity, and wide application, their structures are similar to those of cardiotonic steroids, and there is no research on the application of their derivatives as wound healing drugs. see the report

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
  • Sterol derivative, and preparation method and application thereof
  • Sterol derivative, and preparation method and application thereof
  • Sterol derivative, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0065] Example 1 Sitosta-4-ene-3,6-dione (compound 2)

[0066]Weigh β-sitosterol (compound 1, 1.0 g) and pyridinium chlorochromate (1.0 g), dissolve them in 200 ml of dichloromethane, react at room temperature, and monitor by TLC (thin-layer silica gel plate) until the reaction is complete. After completion of the reaction, cool to room temperature, filter with diatomaceous earth filter cake, and evaporate the solvent under reduced pressure. The residue obtained is subjected to silica gel column chromatography, and the eluent is petroleum ether / ethyl acetate=15:1 (V / V), to obtain light yellow crystal sitoster-4-ene-3,6-dione (compound 2, 854.8mg, yield is 83.1%)

[0067]

[0068] Compound 2: Pale yellow crystals, m.p.ESI-MS m / z: 427.0[M+H]. 1 H NMR (300MHz, CDCl 3 )δ: 0.74 (3H, s, 18-H), 0.83 (3H, d, J=6.0Hz, 26-or 27-H), 0.85 (3H, d, J=6.0Hz, 26-or 27-H ), 0.86(3H, t, J=9.0Hz, 29-H), 0.95(3H, d, J=6.0Hz, 21-H), 1.18(3H, s, 19-H), 2.15-2.18(1H , m, 2-H β ), 2.51-2.57 ...

Embodiment 2

[0069] Example 2 (E)-sitosta-4-ene-3β-oximino-methyl-6-one (compound 3) and (E)-sitosta-3β, 6β-sitosta-methyl-4-ene (compound 4)

[0070] Weigh hydroxylamine hydrochloride (100.0 mg), ethyl acetate (240 μl), sodium hydroxide (126.0 mg), dissolve in 500 μl deionized water, react under ice bath conditions, TLC (thin-layer silica gel plate) monitor until the reaction is complete. After the reaction was completed, methyl bromide (114.1 μl) was added, reacted in an ice bath, and monitored by TLC (thin-layer silica gel plate) until the reaction was complete. After the reaction is complete, extract the by-product with petroleum ether and take the lower layer solution, extract it three times with ethyl acetate, take the ethyl acetate layer, evaporate the solvent under reduced pressure to obtain white crystal methoxyformamide, then add ethanol (10.0ml) . Hydrochloric acid (15 μl), react at 65° C., and monitor by TLC (thin-layer silica gel plate) until the reaction is complete. After ...

Embodiment 3

[0076] Example 3 (E)-sitosta-4-ene-3β-oximino-ethyl-6-ketone (compound 5) and (E)-sitosta-3β, 6β-oximino-ethyl-4-ene ( Compound 6)

[0077] Weigh hydroxylamine hydrochloride (100.0 mg), ethyl acetate (240 μl), sodium hydroxide (126.0 mg), dissolve in 500 μl deionized water, react under ice bath conditions, TLC (thin-layer silica gel plate) monitor until the reaction is complete. After the reaction was completed, ethyl bromide (155.2 μl) was added, reacted in an ice bath, and monitored by TLC (thin-layer silica gel plate) until the reaction was complete. After the reaction is complete, extract the by-product with petroleum ether and take the lower layer solution, extract it three times with ethyl acetate, take the ethyl acetate layer, evaporate the solvent under reduced pressure to obtain white crystal ethoxyformamide, and then add ethanol (10.0ml) , hydrochloric acid (15.0 μl), react at 65° C., and monitor by TLC (thin-layer silica gel plate) until the reaction is complete. ...

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 discloses a sterol derivative of beta-sitosterol, beta-stigmasterol and cholesterol, and is shown as a formula VI. The invention also discloses a preparation method of the sterol derivative. The invention also discloses application of the sterol derivative to the aspect of preparation of wound healing promoting medicine. By starting from easily obtained natural products, the beta-sitosterol, the beta-stigmasterol and the cholesterol are used as starting raw materials; the synthetic method is simple; better operability and reaction yield are realized. The prepared sterol derivative has the obvious wound healing promoting activity; the multiplication, migration and collagen synthesis capability on L929 mechanocytes is obviously higher than that of the raw material and positive control medicine recombinant human bFGF (basic fibroblast growth factor). Compared with protide type medicine (such as bFGF), the prepared sterol derivative has more diversified dosage forms and medication modes; the reference is provided for the application in the field of wound healing promoting. The formula VI is shown as the accompanying diagram.

Description

technical field [0001] The invention belongs to the field of medicine synthesis, and relates to sterol derivatives of β-sitosterol, β-stigmasterol and cholesterol, their preparation methods, and the application of these compounds in promoting wound healing. Background technique [0002] Wound healing refers to the healing process after the body is subjected to external force, and the skin and other tissues are severed or damaged. It is divided into acute wounds (such as penetrating injuries, burns, etc.), chronic wounds (such as venous ulcers, decubitus ulcers), wounds in immunocompromised individuals (such as vascular system damage in the elderly or patients with diabetes and other chronic diseases, etc.) ). Chronic complications such as blindness, nerve damage, kidney failure, heart disease, etc. will result when the damage to the vascular system cannot heal, leading to amputation or even death; and the latest research by Chinese demographers predicts that by 2050, the nu...

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): C07J9/00A61K31/575A61P17/02A61P37/02A61P3/10A61P27/02A61P25/00A61P13/12A61P9/00A23L33/10
CPCA23V2002/00C07J9/00A23V2200/30
Inventor 柳文媛冯锋崔少煜曲玮陈垒谢昕睿孙文卓
Owner CHINA PHARM 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