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

Oleanolic acid-uridine conjugate as well as preparation method and application thereof

A technology of uridine nucleoside conjugates and uridine nucleoside esters, applied in the field of medicine, can solve the problems of weak anti-tumor activity, obstacles and the like

Inactive Publication Date: 2012-08-15
GUANGXI NORMAL UNIV
View PDF6 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Oleanolic acid has good broad-spectrum anti-tumor activity while protecting the liver and liver, and can act on different stages of tumorigenesis, including inhibiting tumor formation, hindering tumor induction and inducing tumor cell differentiation, and effectively inhibiting tumor formation. Angiogenesis prevents tumor cell invasion and metastasis (Ovesna, Z., Vachalkova, A. et al. Pentacyclic triterpenoic acids: New chemoprotective compounds. Neoplasma, 2004, 51(5): 327-333); although olean Acid can act on different stages of tumorigenesis, but its anti-tumor activity is relatively weak (Huang Minshan, Huang Wei, Wu Qinian, etc. Oleanolic Acid-Induced Human Breast Cancer Cell Apoptosis and Intracellular Ca2+ Level Research, Chinese Modern Medicine Journal, 2004, 14(16): 58-60)

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
  • Oleanolic acid-uridine conjugate as well as preparation method and application thereof
  • Oleanolic acid-uridine conjugate as well as preparation method and application thereof
  • Oleanolic acid-uridine conjugate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0070] Example 1: Preparation of 3β-hydroxy-oleanane-12-ene-28-acid-[(uridine-3)-ethyl]ester (I1)

[0071] a) Dissolve 4.99 mmol (2.28 g) of oleanolic acid in 10 mL of DMF, add 24.95 mmol (3.44 g) of potassium carbonate and 5.99 mmol (0.52 mL) of 1,2-dibromoethane, and stir at room temperature for 12 hours, The solvent was spun off under reduced pressure, and the residue was dissolved in 50 mL of ethyl acetate, washed successively with 1N HCl, water, saturated sodium bicarbonate, water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. Purified by silica gel column chromatography, eluted with a mixed solvent of petroleum ether: ethyl acetate = 6: 1 (volume ratio), tracked and detected by thin layer chromatography, collected the eluate, and evaporated the eluate to dryness to obtain 3β-hydroxyl -Oleanane-12-ene-28-acid-(2-bromoethyl)ester 1.60g (white solid, yield 57%); 1 H NMR (500MHz, CDCl 3 )0.74, 0.78, 0.93, 0.99 and ...

Embodiment 2

[0077] Example 2: 3β-Hydroxy-oleanane-12-ene-28-acid-[(uridine-3)-n-butyl]ester (I 2 ) preparation

[0078] a) Dissolve 4.99mmol (2.28g) of oleanolic acid in 10mL of DMF, add 19.96mmol (2.76g) of potassium carbonate and 0.78mL (6.49mmol) of 1,4-dibromobutane, and stir at room temperature for 12 hours, The solvent was spun off, and the residue was dissolved in 50 mL of ethyl acetate, washed successively with 1N HCl, water, saturated sodium bicarbonate, water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated, and the resulting residue was passed through a silica gel column Purified by chromatography, eluted with a mixed solvent of petroleum ether: ethyl acetate = 6: 1 (volume ratio), tracked and detected by thin-layer chromatography, collected the eluate, evaporated the eluate to dryness, and obtained 3β-hydroxy-alcohol Aranane-12-ene-28-acid-(4-bromobutyl)ester 1.78g (white solid, yield 61%); 1 H NMR (500MHz, CDCl 3)0.72...

Embodiment 3

[0084] Example 3: 3β-Hydroxy-oleanane-12-ene-28-acid-[(uridine-3)-n-hexyl]ester (I 3 ) preparation

[0085] a) Dissolve 4.99 mmol (2.28 g) of oleanolic acid in 10 mL of DMF, add 9.98 mmol (1.38 g) of potassium carbonate and 6.24 mmol (0.96 mL) of 1,6-dibromohexane, and stir at room temperature for 12 hours, The solvent was spun off, and the residue was dissolved in 50 mL of ethyl acetate, washed successively with 1N HCl, water, saturated sodium bicarbonate, water and saturated brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated, and the resulting residue was passed through a silica gel column Purified by chromatography, eluted with a mixed solvent of petroleum ether: ethyl acetate = 8: 1 (volume ratio), tracked and detected by thin layer chromatography, collected the eluate, evaporated the eluate to dryness, and obtained 3β-hydroxy-alcohol Aranane-12-ene-28-acid-(6-bromohexyl)ester 1.80g (white solid, yield 58%); 1 H NMR (500MHz, CDCl ...

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 an oleanolic acid-uridine conjugate and a preparation method thereof as well as application of the oleanolic acid-uridine conjugate in the pharmaceutical field. An applicant finds that the anti-tumor activity of the oleanolic acid-uridine conjugate is higher than that of a parent body namely oleanolic acid, and a lead compound is provided for developing new anti-tumor medicaments. The conjugate has a structure as shown in the following general formula (I) or (II).

Description

technical field [0001] The invention relates to the technical field of medicine, in particular to an oleanolic acid-uridine conjugate and a preparation method and application thereof. Background technique [0002] Tumor is a disease that seriously threatens human health, and the death caused by various tumor diseases is the second leading cause of death after cardiovascular disease. In recent years, tumor chemotherapy has made considerable progress, and the survival time of cancer patients has been significantly prolonged, especially breakthroughs have been made in the treatment of leukemia and malignant lymphoma. The treatment of more than 90% solid tumors has not yet achieved satisfactory results. Therefore, experts in the field of medicine in my country are constantly researching new drugs and looking for new ways. [0003] Oleanolic acid is an oleanane-type pentacyclic triterpenoid compound, widely distributed in nature, and has various biological activities such as prot...

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 Applications(China)
IPC IPC(8): C07J63/00A61P35/00
Inventor 程克光梁宏苏春华陈振锋王恒山莫伟彬
Owner GUANGXI NORMAL 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