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Alpha-helexin derivatives, and preparation method and application thereof

A technology of hedera saponins and derivatives, which is applied in the production of drug combinations, steroids, and bulk chemicals, and can solve problems such as multidrug resistance, poor curative effect of solid tumors, and large toxic and side effects

Active Publication Date: 2016-12-14
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although chemical drugs have a significant effect on cancer, the anti-tumor drugs commonly used in clinical practice generally have many shortcomings such as poor curative effect on solid tumors, large toxic and side effects, and easy multidrug resistance.

Method used

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  • Alpha-helexin derivatives, and preparation method and application thereof
  • Alpha-helexin derivatives, and preparation method and application thereof
  • Alpha-helexin derivatives, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0079] Benzyl 3-oximino-23-hydroxy-olean-12-en-28-ate

[0080] Take a 50mL eggplant-shaped bottle, dissolve 3β,23-dihydroxy-olean-12-ene-28-acid (472mg, 1mmol) in N,N-dimethylformamide (15mL), add potassium carbonate ( 300mg, 2.1mmol), benzyl bromide (0.15mL, 1.25mmol), and stirred at 50°C for 8-10 hours. The reaction solution was diluted with ethyl acetate (25 mL), washed three times with water, washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, evaporated to remove the solvent under reduced pressure, and subjected to silica gel column chromatography (V 石油醚 :V 乙酸乙酯 =15:1~8:1), white solid X was obtained 1 (470 mg, 83%). m.p. 220-223°C.

[0081] Take a 50mL eggplant bottle, put compound X 1 (460mg, 0.81mmol) was dissolved in 20mL of dichloromethane, 4-dimethylaminopyridine (122mg, 1mmol) and tert-butyldimethylsilyl chloride (36omg, 2.4mmol) were added, and stirred at room temperature for 6-8 hours. Dichloromethane was distilled off, diluted...

Embodiment 2

[0088] 2-(3-Carbonyl-olean-12-ene-28 acid benzyl ester-23-oxyl)-carbonyl-benzoic acid

[0089] 25mL eggplant bottle, compound X 2(56mg, 0.1mmol) was dissolved in anhydrous dichloromethane (8mL), the catalyst DMAP (10mg, 0.08mmol) and phthalic anhydride (15mg, 0.15mmol) were added, and the reaction was carried out at room temperature for 8-15 hours. After the end, add 10mL of dichloromethane to dilute, the organic layer was washed once with 5% HCl solution, deionized water and saturated sodium chloride solution twice, dried over anhydrous sodium sulfate, filtered, concentrated, silica gel column chromatography (V 氯仿 :V 甲醇 =50:1~30:1), a white solid was obtained with a yield of 56%. m.p. 280-283°C.

[0090] 1 H-NMR (CDCl 3 , 400MHz) δ (ppm): 0.64 (3H, s, -CH 3 ), 0.88 (3H, s, -CH 3 ), 0.91 (3H, s, -CH 3 ), 1.03 (3H, s, -CH 3 ), 1.06 (3H, s, -CH 3 ), 1.07 (3H, s, -CH 3 ), 2.44-2.52 (2H, m), 2.89 (1H, dd, J=3.9, 13.6Hz, H-18), 4.30 (1H, d, J=10.72Hz, H-23A), 4.32 (1H, ...

Embodiment 3

[0092] 4-(3-Carbonyl-olean-12-ene-28 acid benzyl ester-23-oxyl)-4-oxo-butyryl-p-aminoaniline

[0093] Take compound X 2 And succinic anhydride as raw material, the implementation refers to 2-(3-carbonyl-olean-12-ene-28 acid benzyl ester-23-oxygen

[0094] Base)-carbonyl-benzoic acid preparation method, silica gel column chromatography (V 氯仿 :V 甲醇 =50:1~30:1), white solid X 3 (45mg, 70%). m.p. 310-313°C.

[0095] 1 H-NMR (CDCl 3 , 400MHz) δ (ppm): 0.65 (3H, s, -CH 3 ), 0.90 (3H, s, -CH 3 ), 0.92 (3H, s, -CH 3 ), 1.01 (3H, s, -CH 3 ), 1.03 (3H, s, -CH 3 ), 1.13 (3H, s, -CH 3 ), 2.33-2.39 (1H, m, H-2A), 2.47-2.51 (1H, m, H-2B), 2.59-2.67 (4H, m), 2.92 (1H, dd, J=3.9, 13.9Hz, H-18), 4.13 (2H, s, H-23), 5.08 (1H, d, CH 2 Ar), 5.10 (1H, d, CH 2 Ar), 5.31 (1H, t, H-12), 7.31-7.36 (5H, m, H-Ar).

[0096] Take a 25mL eggplant-shaped bottle, dissolve p-phenylenediamine (10mg, 0.092mmol) in anhydrous dichloromethane, and stir at room temperature. Compound X 3 (20mg, 0.0...

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Abstract

The invention relates to the fields of organic synthesis and pharmaceutical chemistry, and particularly discloses novel-structure alpha-helexin derivatives. The invention also discloses a preparation method of the triterpene saponin derivatives, a pharmaceutical composition containing the derivatives, and application of the derivatives in resisting neoplastic diseases.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of novel α-hedera saponin derivatives, a pharmaceutical composition containing the same, a preparation method thereof and an antitumor application. technical background [0002] Malignant tumors are one of the major diseases that seriously threaten human health. Finding effective anti-tumor drugs and methods to completely conquer cancer is a worldwide problem. Although chemical drugs have significant curative effects on cancer, the anti-tumor drugs commonly used in clinical practice generally have many disadvantages such as poor curative effect on solid tumors, high toxicity and side effects, and multi-drug resistance. Therefore, it is of great significance to improve the therapeutic ability of tumors and find effective therapeutic drugs. [0003] In contrast, natural anticancer drugs have shown the advantages of good curative effect and low sid...

Claims

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Application Information

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IPC IPC(8): C07J63/00A61P35/00
CPCY02P20/55C07J63/008
Inventor 王洪波毕毅傅风华杨延婷刘泽云刘现轩杨剑管道坤
Owner YANTAI UNIV
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