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Pentacyclic triterpene-13,28-lactone compounds as well as preparation method and application thereof

A technology of pentacyclic triterpene and compound, which is applied in the preparation of anti-tumor drugs. In the field of pentacyclic triterpene-13, it can solve the problems of narrow application range and easy damage of pentacyclic triterpene lactone, and achieve excellent anti-tumor Activity, fewer side effects, and easy post-processing effects

Inactive Publication Date: 2011-06-01
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Furthermore, the preparation of oleanane lactones by the peroxide method is easy to destroy some sensitive groups on the substrate structure, such as double bonds, hydroxyl groups, amino groups, etc.
Therefore, peroxide method prepares the scope of application of pentacyclic triterpene lactone narrower

Method used

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  • Pentacyclic triterpene-13,28-lactone compounds as well as preparation method and application thereof
  • Pentacyclic triterpene-13,28-lactone compounds as well as preparation method and application thereof
  • Pentacyclic triterpene-13,28-lactone compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0120] Preparation of 3β-hydroxyoleanane-12-ene-28-carboxylic acid benzyl ester (5)

[0121] Put oleanolic acid (100g, 220mmol) and potassium carbonate (61g, 440mmol) in DMF (800mL), add benzyl chloride (33mL, 290mmol) dropwise within 20 minutes at 50~55℃, after the addition is complete Maintain the temperature to continue the reaction for 3 to 4 hours, cool the reaction solution to room temperature, filter, and wash the filter cake with DMF (50mL×3). The obtained mother liquor is poured into ice water (3000mL). A large amount of white solid precipitates out. After the solid particles became larger, they were filtered with suction, washed thoroughly with water, and dried to obtain a white solid 5 (114 g, 95.5%). Compound 5 is a known compound with CAS number 303114-51-4.

Embodiment 2

[0123] Preparation of 3β-acetoxy oleanorane-12-ene-28-carboxylic acid benzyl ester (6)

[0124] Compound 5 (5.46g, 10mmol) was dissolved in pyridine (20mL). Acetic anhydride (10.2g, 100mmol) was slowly added dropwise at 0°C. After the addition was completed, DMAP (0.12g, 1mmol) was added. A solid precipitated out at room temperature. Continue the reaction for 1 to 2 hours, add an appropriate amount of dichloromethane (50mL) to dissolve, the solution is washed with 5% dilute hydrochloric acid solution, saturated sodium bicarbonate solution, saturated sodium bicarbonate solution 3 times each, dried over anhydrous sodium sulfate, and the solvent removed under reduced pressure A white solid 6 (5.4 g, 91.3%) was obtained. Compound 6 is a known compound with CAS number 357953-27-6.

Embodiment 3

[0126] Preparation of 3β-acetoxy-12-oxo-oleanane-28-carboxylic acid benzyl ester (7)

[0127] Compound 6 (5.88g, 10mmol) was dissolved in appropriate amount of dichloromethane (50mL), formic acid (10mL) was added, H 2 O 2 (1.36g, 40mmol), react at room temperature for 24 hours. TLC monitors the progress of the reaction. After the raw material points disappear, the reaction solution is washed to near neutral with saturated sodium bicarbonate solution, washed with saturated sodium bicarbonate solution 3 times, and dried with anhydrous sodium sulfate. After removing the solvent under reduced pressure, a light yellow solid, AcOH-H 2 O was recrystallized to obtain white solid 7 (4.7 g, 78%). Compound 7 is a known compound with CAS number 357953-28-7.

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Abstract

The invention discloses pentacyclic triterpene-13,28-lactones with antineoplastic activity, shown as a general formula I, or pharmaceutically acceptable salts thereof as well as a preparation method and medical application thereof, belonging to the field of biological medicines. The preparation method of the compounds, provided by the invention, has the advantages of mild reaction conditions, simplicity in operation, higher yield as well as strong practicability and structural universality. Shown by a pharmacologic test result, the compounds provided by the invention have favorable antineoplastic activity and can be applied as an antineoplastic drug in clinic.

Description

Technical field [0001] The invention relates to the field of medicine, in particular to a class of pentacyclic triterpene-13,28-lactone compounds and a preparation method thereof. The invention further relates to their application in the preparation of antitumor drugs. Background technique [0002] Five-ring triterpenoids such as oleanane and ursane are widely distributed in the plant kingdom. They are the main effective ingredients of many commonly used Chinese herbal medicines and have a wide range of biological activities (Neoplasma, 2004, 51, 327-333). The optimization and derivatization based on the structure of these natural compounds is one of the hotspots of natural medicinal chemistry research. [0003] [0004] Recent studies have found that oleanane-13,28-lactone, an important member of natural pentacyclic triterpenoids, has significant anti-tumor activity. For example, the lactones (1, 2) isolated from the roots of platycodon grandiflorum by Zhang et al. showed potent...

Claims

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Application Information

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IPC IPC(8): C07J63/00C07J71/00A61K31/585A61P35/00
Inventor 张奕华丁晔赖宜生张士薄黄张建彭司勋
Owner CHINA PHARM UNIV
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