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Oleanolic acid and its derivative, preparation method and use

A technology of oleanolic acid and derivatives is applied in the fields of oleanolic acid and derivatives thereof, preparation method and use, and can solve the risk of breast cancer and endometrial cancer, and the long-term use effect of bisphosphonates is not completely confirmation, etc.

Inactive Publication Date: 2006-01-25
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although hormone replacement therapy is the first choice for the prevention and treatment of postmenopausal osteoporosis, long-term use has the potential risk of breast cancer and endometrial cancer
The long-term effects of bisphosphonates have not been fully proven
Especially on oleanolic acid derivatives and anti-osteoporosis activity, there are no other research papers

Method used

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  • Oleanolic acid and its derivative, preparation method and use
  • Oleanolic acid and its derivative, preparation method and use
  • Oleanolic acid and its derivative, preparation method and use

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Example 1: The 3-hydroxyl of oleanolic acid 1 is protected with acetyl, and then the methylene at the 11-position is oxidized with the reagent of (b), and the protective group is removed to obtain derivative 2, as follows:

[0036] a: Add 4.57g (10mmol) oleanolic acid 1 to 19mL pyridine, add 9.45mL acetic anhydride dropwise under ice bath stirring, remove the ice bath after dissolving, add 122mg (1mmol) DMAP, react for about 2h, TLC (acetic acid ethyl ester: petroleum ether=1: 3, V: V) to detect the reaction progress, after the reaction, the reaction solution was poured into 50mL of ice water, and washed with 20mLCH 2 Cl 2 Extract three times. The extract was washed with 5% HCl, water, and saturated brine respectively, the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent was evaporated to obtain 4.93 g of 3-O-acetyl oleanolic acid 12 with a yield of 99%.

[0037] b: 45mLCCl 4 5.8g of 12 was added in , and 11.2mL of glacial acetic acid ...

Embodiment 2

[0040] Example 2: 13Δ 11-12 ,Δ 14-18 Preparation of oleanolic acid 4:

[0041] a. Add 0.996g (2mmol) 12 to 50mL methanol, add 1.25gBr dropwise 2 (7.7mmol) dissolved in 50mL methanol solution. After stirring at room temperature for 0.5 h, the mixture was cooled in an ice bath and filtered to obtain 0.7 g of 14 with a yield of 63%.

[0042] b: Add 6g of 14 to 100mL of o-xylene, dissolve it, add 23mL of DBU, and stir under reflux for 16h. The reaction solution was separated with ether and water, and the organic layer was washed with 5% HCl, saturated NaHCO3 and saturated brine, and dried over anhydrous sodium sulfate. After filtering, part of the solvent was evaporated, cooled and left standing, crystals were precipitated, and filtered to obtain 3.84g of 15 with a yield of 72%.

[0043] c: Add 3 g of 15 to 100 mL of 9% HCl in methanol and stir at room temperature for half an hour. TLC (CHCl3:petroleum ether=1:1) detected the progress of the reaction. After the reaction was...

Embodiment 3

[0045] Example 3: Acylate the carboxyl group of oleanolic acid derivative 12 using the conditions in the figure (a) below to obtain compound 17, and at the same time prepare the amino acid methyl ester hydrochloride protected by the amino acid carboxyl group with the reagent (b) . Reaction of 17 and amino acid methyl ester hydrochloride under the conditions of (c) to obtain derivatives 12a-12g, deprotection under the conditions of the following figure (d) to obtain derivatives 1a-1g. The amino acids used therein are all naturally occurring amino acids and artificially synthesized D-type amino acids.

[0046] a: Dissolve 6.00 g (12 mmol) of 12 in 80 mL of dichloromethane, then add 4.4 mL of oxalyl chloride dropwise, and react at room temperature for 24 h. After the reaction, the solvent was evaporated to dryness, then 5×300 mL cyclohexane was added, and evaporated to dryness to obtain 3-O-acetyl oleanene-28-acyl chloride 17. Proceed directly to the next reaction.

[0047] c:...

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Abstract

Disclosed is the derivatives of oleanolic acid parent nucleus which introduces functional groups including carbonyl, hydroxyl and double bonds, the oleanolic acid derivatives 1-9 have the molecular structure disclosed in the specification, the preparing process for the oleanolic acid consists of protecting the 3-hydroxy of the oleanolic acid 1 with acetyl, reacting and removing protecting groups. The invention can be applied into the preparation of medicament and health food for resisting osteoporosis.

Description

1. Technical field [0001] The invention relates to a series of derivatives synthesized from oleanolic acid, a preparation method and application as an anti-osteoporosis drug and related health food. 2. Background technology [0002] Osteoporosis is known as a silent epidemic. It is a common and complex disease in middle-aged and elderly people characterized by decreased bone tissue mass and microstructural degeneration, resulting in increased bone fragility and susceptibility to fracture. According to the statistics of the World Health Organization, there are currently more than 200 million people with osteoporosis. There are 10 million patients in the United States with an estimated direct medical cost of $14 billion. It is estimated that Japan has now reached 10 million, and there is a tendency to continue to increase. With the continuous acceleration of population aging in my country, the number of patients with osteoporosis is increasing rapidly, and it has become a fr...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61K31/704A61P19/10A23L1/30A23L33/10
CPCY02P20/55
Inventor 李建新
Owner NANJING UNIV
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