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

A technology of uridine nucleoside conjugate and uridine nucleoside ester, which is applied in the field of medicine and can solve the problems of hindering differentiation and weak anti-tumor activity.

Inactive Publication Date: 2014-06-18
GUANGXI NORMAL UNIV
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  • 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 antitumor activity is relatively weak (Huang Minshan, Huang Wei, Wu Qinian, etc. Oleanolic acid induces apoptosis of human breast cancer cells and interacts with intracellular Ca 2+ Level of research, Chinese Journal of Modern Medicine, 2004, 14(16): 58-60)

Method used

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  • 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

[0071] Example 1: 3β-Hydroxy-oleanane-12-ene-28-oic acid-[(uridine-3)-ethyl]ester (I 1 ) preparation

[0072] a) Dissolve 4.99mmol (2.28g) of oleanolic acid in 10mL of DMF, add 24.95mmol (3.44g) of potassium carbonate and 5.99mmol (0.52mL) 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, evaporated the eluate to dryness, and obtained 3β-hydroxyl -Oleanane-12-ene-28-acid-(2-bromoethyl)ester 1.60g (white solid, yield 57%); 1 H NMR (500MHz, CDCl 3 )0.74,0.78,0.93,0.99and1.14(5s,e...

Embodiment 2

[0078] Example 2: 3β-Hydroxy-oleanane-12-ene-28-acid-[(uridine-3)-n-butyl]ester (I 2 ) preparation

[0079]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

[0085] Example 3: 3β-Hydroxy-oleanane-12-ene-28-acid-[(uridine-3)-n-hexyl]ester (I 3 ) preparation

[0086] 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 3...

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Abstract

The invention discloses an oleanolic acid-uridine conjugate, a preparation method thereof, and application of the oleanolic acid-uridine conjugate in the field of pharmacy. The applicant discovers that the oleanolic acid-uridine conjugate has much higher anti-tumor activity than oleanolic acid, a matrix of the oleanolic acid-uridine conjugate, and a lead compound is provided for developing new anti-tumor drugs. The conjugate has a structure of the general formula (II) shown in the specification.

Description

[0001] This application is a divisional application of "Oleanolic acid-uridine nucleoside conjugate and its preparation method and application". The filing date of the original application is: March 31, 2012, the application number is: 201210092637.9, and the title of the invention For: oleanolic acid-uridine nucleoside conjugate and its preparation method and application. technical field [0002] 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 [0003] 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...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/7072A61P35/00
Inventor 程克光梁宏苏春华陈振锋王恒山莫伟彬
Owner GUANGXI NORMAL UNIV
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