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Ursolic acid derivative with antitumor activity and preparation method thereof

A technology of anti-tumor activity and ursolic acid, which is applied in the direction of anti-tumor drugs, organic chemistry, drug combination, etc., can solve the problem of low reaction yield, achieve high yield, suitable for clinical application, and significant anti-proliferation ability Effect

Active Publication Date: 2017-07-14
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the literature reported by Meng Yanqiu et al., the reaction yields of oleanolic acid bromoethanol ester derivatives with secondary amines were all lower than 10%.

Method used

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  • Ursolic acid derivative with antitumor activity and preparation method thereof
  • Ursolic acid derivative with antitumor activity and preparation method thereof
  • Ursolic acid derivative with antitumor activity and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] Synthesis of compound Ⅰ-1:

[0039] Add UA (2.0g, 4.38mmol) into a 50mL eggplant-shaped bottle, dissolve it in 15mL of pyridine, control the temperature at 0°C to 10°C, slowly add acetic anhydride (1.0mL, 10.58mmol) dropwise, and stir the reaction at room temperature after the dropwise addition 14h, TLC (cyclohexane / acetone=3:1) detection showed that the reaction was complete. The reaction solution was poured into 60 mL of ice water, solids were precipitated, filtered with suction, and the filter cake was dissolved in 100 mL of ethyl acetate, washed with 1 mol / L hydrochloric acid, distilled water, and saturated aqueous sodium chloride solution, and dried overnight over anhydrous sodium sulfate. Concentrate under reduced pressure and dry in vacuo to obtain 2.02 g of 3-acetoxy-UA (2), with a yield of 92.5%.

[0040] Add compound 2 (1.16g, 2.33mmol) to a 50mL eggplant-shaped bottle, dissolve it in 15mL DMF, add 2-chloroethanol (0.58g, 7.20mmol), potassium carbonate (0.49g...

Embodiment 2

[0046] Synthesis of compound Ⅰ-4:

[0047] Referring to the synthesis method of compound I-1 in Example 1, but substituting homopiperazine for anhydrous piperazine, a yellow-white powder was obtained with a total yield of 70.2%. mp: 76.5-78.0°C.

[0048] 1 H NMR (400MHz, CDCl 3 )δ5.22(1H,s,H-12),4.53–4.44(1H,m,H-3),4.16(2H,s,CH 2 ),3.38(4H,s,H in homopiperazine),3.20(2H,s,CH 2 ), 2.97 (4H, d, J=24.4Hz, H inhomopiperazine), 2.04 (3H, s, CH 3 ),1.06(3H,s,CH 3 ),0.94(6H,d,J=3.8Hz,2×CH 3 ),0.85(9H,d,J=4.6Hz,3×CH 3 ),0.72(3H,s,CH 3 ).

[0049] HR-MS: calcd for C 39 h 65 N 2 o 4 [M+H] + 625.49388; found 625.49126.

Embodiment 3

[0051] Synthesis of compound Ⅰ-8:

[0052] Add compound Ⅰ-1 (60mg, 0.098mmol) to a 10mL chicken heart bottle, dissolve it in 2mL of DMF, add potassium carbonate (17mg, 0.123mmol), 4-fluorobenzyl bromide (0.02mL, 0.161mmol), and react in an oil bath at 60°C After 30 min, TLC (dichloromethane / methanol=20:1) showed that the reaction was complete. After natural cooling, it was extracted with 50 mL of ethyl acetate and 30 mL of water, the organic phase was washed twice with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and purified by preparative TLC (dichloromethane / methanol=20:1) to obtain the product 29.8 mg (I-8), yellow-white powder, yield 42.3%, mp: 140.0-141.8 °C.

[0053] 1 H NMR (400MHz, CDCl 3 )δ7.76–7.58(2H,m,ArH),7.12(2H,t,J=8.2Hz,ArH),5.16(1H,s,H-12),4.51–4.43(1H,m,H-3 ),4.08(2H,s,CH 2 ),2.73–3.90(10H,m,CH 2 and 4×CH 2 inpiperazine), 2.09 (1H, d, J=11.3Hz, H-18), 2.04 (3H, s, CH 3 ),1.04(3H,d,J=7.4Hz,CH 3 ),0.92(6H,d,J=10.4Hz...

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Abstract

The invention discloses an ursolic acid derivative with antitumor activity and a preparation method and application thereof. A series of ursolic acid derivatives with antitumor activity is synthesized. An in-vitro pharmacological test shows that the ursolic acid derivative synthesized in the invention has remarkable antiproliferative activity on Hela and MNK45 tumor cells, and has wide application in preparing an antitumor drug.

Description

technical field [0001] The invention relates to ursolic acid derivatives, a preparation method of ursolic acid derivatives and an application in the antitumor field. Background technique [0002] Ursolic acid (Ursolic acid, UA), also known as ursolic acid, ursolic acid, belongs to pentacyclic triterpenoids, chemical name 3(β)-3-Hydroxyurs-12-en-28-oic acid, its relative The molecular weight is 456.68, and the molecular formula is C 30 h 48 o 3 , is an active compound widely distributed in plant resources. Pharmacological studies have shown that UA has various effects such as antiviral, antibacterial, antitumor, antiosteoporosis, antioxidation, antiinflammation, treatment of diabetes and liver protection. UA has poor water solubility and lacks target specificity, which limits its clinical application. [0003] The chemical structure of ursolic acid: [0004] [0005] UA has broad-spectrum anticancer activity. Studies have shown that the mechanism of UA’s antitumor ef...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00C07J71/00A61P35/00
CPCC07J63/008C07J71/0063
Inventor 孟庆国王洪波赵风兰王文智雷蕾刘娟杨静静王朝明刘智王嘉珍
Owner YANTAI UNIV
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