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
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
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.
PUM
Abstract
Description
Claims
Application Information
- R&D Engineer
- R&D Manager
- IP Professional
- Industry Leading Data Capabilities
- Powerful AI technology
- Patent DNA Extraction
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