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Oleanolic acid derivative with function of resisting malignant tumor, as well as preparation method and applications of oleanolic acid derivative

A compound and straight-chain technology, applied in the field of medicine, can solve problems such as tissue and organ damage, death, and lower quality of life of patients

Active Publication Date: 2012-12-26
TIANJIN INSTITUTE OF PHARMA RESEARCH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] However, there are few reports on improving its anti-tumor activity through structural modification.
At present, most of the anti-tumor drugs commonly used in clinical practice have strong toxic and side effects, and even cause damage to normal tissues and organs. The treatment will cause great pain, seriously reduce the quality of life of patients, and even lead to death.

Method used

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  • Oleanolic acid derivative with function of resisting malignant tumor, as well as preparation method and applications of oleanolic acid derivative
  • Oleanolic acid derivative with function of resisting malignant tumor, as well as preparation method and applications of oleanolic acid derivative
  • Oleanolic acid derivative with function of resisting malignant tumor, as well as preparation method and applications of oleanolic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] Reference Example 1: Synthesis of Intermediate II

[0064]

[0065] Dissolve 4.57g (0.01mol) of oleanolic acid in 25mL of dichloromethane, add dropwise 30mL of 5.40g (0.025mol) of PCC in dichloromethane, then add the same amount of diatomaceous earth as PCC, and stir the reaction at room temperature , TLC to monitor the progress of the reaction. Filter after completion of the reaction, wash the filtrate with 3×50mL water, separate the dichloromethane layer, fully dry it with anhydrous sodium sulfate, filter, evaporate the dichloromethane under reduced pressure, and separate the column [mobile phase: v (petroleum ether): v(ethyl acetate)=4:1] to obtain 2.77 g of white solid product (HPLC: 99.3%), yield 60.8%.

Embodiment 2

[0066] Reference Example 2: Synthesis of Intermediate Ⅲ-1

[0067]

[0068] Add 4.55g (0.01mol) of intermediate II to a reaction flask equipped with a stirring, condenser and thermometer, dissolve it with 30mL of anhydrous methanol, and add 10mL of pyridine while stirring. Add 2.78g (0.04mol) of hydroxylammonium hydrochloride to the reaction system in batches. After the addition was complete, the reaction was continued at 50°C for 3.5h (the plate showed that the reaction was complete). Evaporate anhydrous methanol to dryness, wash the reaction solution with 3 × 30mL water, extract with dichloromethane, fully dry over anhydrous sodium sulfate, filter, and evaporate dichloromethane under reduced pressure to obtain 2.0 g of white solid (HPLC: 94.5% ), the yield was 43.5%.

Embodiment 3

[0069] Reference Example 3: Synthesis of Intermediate Ⅲ-2

[0070]

[0071] Add 4.55 g (0.01 mol) of intermediate II to a reaction flask equipped with stirring, a condenser, and a thermometer, dissolve it with 25 mL of acetone, and add 2.24 g of potassium hydroxide while stirring. 3.34g (0.04mol) methoxyamine hydrochloride was added to the reaction system in batches. After the addition was complete, the reaction was continued at 40°C for 2h (the plate showed that the reaction was complete). Evaporate the acetone to dryness, wash the reaction liquid with 3×30mL water, extract with dichloromethane, fully dry with anhydrous sodium sulfate, filter, evaporate dichloromethane under reduced pressure to obtain 3.0g of white solid (HPLC: 96.7%), Yield 62.5%.

[0072] Reference Example 4: Synthesis of Intermediate Ⅲ-3

[0073]

[0074] Add 4.55 g (0.01 mol) of intermediate II to a reaction flask equipped with stirring, a condenser, and a thermometer, dissolve it with 40 mL ...

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Abstract

The invention belongs to the technical field of medicines for resisting malignant tumors and discloses an oleanolic acid derivative with a structure shown as formula I, wherein R1 stands for a hydrogen; C1-C4 stands for a straight-chain or a branch-chain alkyl; R2 is an ethyl which is substituted by a halogen, a hydroxyl, a C1-C4 straight-chain or a branch-chain alkyl or a C1-C4 straight-chain or a branch-chain alkoxy. Furthermore, the invention relates to a method for preparing the compound, as well as pharmaceutical compositions taking the compound as an active and effective ingredient and applications of the pharmaceutical compositions as medicines for resisting the malignant tumors.

Description

technical field [0001] The invention belongs to the technical field of medicine, more specifically, relates to a class of compounds with anti-malignant tumor effects and a preparation method thereof. Background technique [0002] Oleanic acid (OA) is also known as soil angelica acid and Qingsisu. It exists widely in nature in the free form or combined into glycosides. Especially in plants such as the whole grass of green leaves, privet fruit, hedyotis diffusa, hawthorn, clove, jujube, loquat leaves, and Prunella vulgaris. OA is an oleane-type pentacyclic triterpenoid compound, white needle-like crystal, insoluble in water, soluble in ethanol, chloroform, ether, acetone, due to its wide distribution in nature and its complex structure, it is difficult to synthesize artificially. At present, it is mainly extracted from Chinese medicinal plants. A large number of studies at home and abroad have shown that OA has pharmacological effects such as protecting the liver and reduci...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00A61K31/56A61P35/00A61P35/02
Inventor 刘颖刘登科解晓帅祁浩飞王景阳
Owner TIANJIN INSTITUTE OF PHARMA RESEARCH
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