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

A macrocyclic oxidation substituted pentacyclic triterpanoids derivative and preparation method and use thereof

A technology of pentacyclic triterpenoids and compounds, which is applied in the field of organic chemistry and medicinal chemistry, and can solve problems such as research in the ascendant

Inactive Publication Date: 2008-02-06
ZHEJIANG HISUN PHARMA CO LTD
View PDF0 Cites 26 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, research on this enzyme and its inhibitors is in the ascendant

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
  • A macrocyclic oxidation substituted pentacyclic triterpanoids derivative and preparation method and use thereof
  • A macrocyclic oxidation substituted pentacyclic triterpanoids derivative and preparation method and use thereof
  • A macrocyclic oxidation substituted pentacyclic triterpanoids derivative and preparation method and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Embodiment 1: the preparation of compound Ig

[0039]Under ice-salt bath, ursolic acid (1.0 mmol) was dissolved in 10 ml of dichloromethane, 6 ml of triethylamine was added, and methanesulfonyl chloride (16.3 mmol) was added dropwise at 0°C. Stir at room temperature for 4 hours. After filtering, the filtrate was washed with 5 ml of 1 mol / L hydrochloric acid solution, washed with water until neutral, and dried over anhydrous magnesium sulfate. Precipitation under reduced pressure gave 3β-methylsulfonyloxy-arbutane-28-acid-12-ene. Dissolve in 10 ml of acetic acid (containing 0.5 ml of acetic anhydride), add chromium trioxide (4.0 mmol), and stir overnight at room temperature. 10 ml of water and 10 ml of dichloromethane were added to the reaction solution, and the layers were separated, and the aqueous layer was extracted with 10 ml of dichloromethane. The organic layers were combined, washed with 10 ml of saturated sodium bicarbonate solution, washed with water until n...

Embodiment 2～ Embodiment 9

[0042] According to the method of Example 1, the compounds of Example 2 to Example 9 shown below were prepared

Embodiment 2

[0043] Example 2: Preparation of 11-carbonyl-arbutane-28-acid-2,12-diene (Ia), C 30 h 44 o 3 , MS: ESI m / e 452 (M + ); Rf[(petroleum ether / ethyl acetate: 3 / 1)+1%HCOOH]: 0.60; 1 HNMR (400MHz) δ: 0.87(d, 3H, J=6.0Hz), 0.97(d, 3H, J=6.4Hz), 5.36(dd, 1H, J=2.0, 10.0Hz, H-3), 5.43( dd, 1H, J=5.6, 10.0 Hz, H-2), 5.62 (s, 1H, H-12).

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 relates to a pentacyclic triterpanoid derivative of multiple-oxide substitution of the A ring and the medicine salt or solvate of the derivative, and the present invention also relates to the preparation method, the drug combination, and medical use of the derivative. The compound of the present invention has the functions of inhibiting the activity of six human tumor cell strains in vitro, such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cells (CNE), oral squamous carcinoma cell(KB), human lung cancer cell (A549), human hepatoma cell (BEL-7404), and human cervix cancer cell (Hela), and the function of the invention is at the same magnitude of the positive control of cisplatin, thereby the compound can be used as expected antitumor drug. The compound of the present invention also inhibits the alpha glucosidase strongly, and the inhibiting effect is greater than the positive control of acarbose, thereby the compound can be used as expected medicine for preventing and treating diabetes and the treatment of the virus diseases.

Description

technical field [0001] The invention relates to the fields of organic chemistry and medicinal chemistry, in particular, the invention relates to pentacyclic triterpene derivatives substituted by polyoxygenation of the A ring, a preparation method and application thereof. The present invention treats the series of compounds on six tumor cell lines such as human prostate cancer cell (PC-3), nasopharyngeal carcinoma cell (CNE), oral cavity epithelial cancer cell (KB), human lung cancer cell (A549), human liver cancer cell ( BEL-7404), human cervical cancer cells (Hela) were screened for tumor cell growth inhibitory activity. The compounds are found to have a certain activity of inhibiting the growth of tumor cells, and can be expected to be used as antitumor drugs. The present invention also finds that such compounds have a strong inhibitory effect on α-glucosidase, and can be expected to be used as medicines for preventing and treating diabetes and treating viral diseases. Ba...

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): C07J63/00C07J53/00A61K31/56A61P35/00A61P3/10
CPCY02P20/55
Inventor 赵昱冯菊红巫秀美白骅约阿施·史托克希特
Owner ZHEJIANG HISUN PHARMA CO LTD
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