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Alpha-hederagenin derivative with tumor drug-resisting reversion activity as well as preparation method and application thereof

A technology of helexin and derivatives, which can be used in anti-tumor drugs, organic active ingredients, medical preparations containing active ingredients, etc., can solve the problem of tumor patients unable to obtain therapeutic effects and other problems

Active Publication Date: 2017-05-31
YANTAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Tumor multidrug resistance (MDR) induced by chemical drugs prevents cancer patients from obtaining sustained and effective therapeutic effects, which poses a severe challenge to modern cancer treatment and anti-tumor drug development

Method used

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  • Alpha-hederagenin derivative with tumor drug-resisting reversion activity as well as preparation method and application thereof
  • Alpha-hederagenin derivative with tumor drug-resisting reversion activity as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0082] 23-Hydroxy-olean-12-en-28-oic acid benzyl[3,2-b]pyrazine

[0083] Compound (3β,4α)-3,23-dihydroxy-olean-12-ene-28-oic acid (472 mg, 1 mmol) was dissolved in N,N-dimethylformamide (15 mL), and potassium carbonate was added (300mg, 2.1mmol), benzyl bromide (0.15mL, 1.25mmol), stirred at 50°C for 6-10 hours. The reaction solution was diluted with ethyl acetate (25mL), washed three times with water, washed twice with saturated brine, dried over anhydrous sodium sulfate, filtered, the solvent was evaporated under reduced pressure, and silica gel column chromatography (V 石油醚 :V 乙酸乙酯 = 10:1-5:1), a white solid (470mg, 83%) was obtained.

[0084] The above compound (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 4- 8 hours. dichloromethane was distilled off, diluted with ethyl acetate (20mL), washed with 5% hydrochloric aci...

Embodiment 2

[0089] 4-(Olean-12-en-28-oic acid benzyl ester-23-oxo[3,2-b]pyrazine)-4-oxo-butanoic acid

[0090] The compound 23-hydroxy-olean-12-en-28-acid benzyl[3,2-b]pyrazine (56 mg, 0.1 mmol) was dissolved in anhydrous dichloromethane (8 mL), and added Catalyst DMAP (10 mg, 0.08 mmol) and succinic anhydride (15 mg, 0.15 mmol), react at room temperature for 8-15 hours, after the reaction, add 10 mL of dichloromethane for dilution, and the organic layer is washed successively with 5% HCl solution Once, washed twice with deionized water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered, concentrated, silica gel column chromatography (V 氯仿 :V 甲醇 = 50:1~20:1), a white solid was obtained with a yield of 75%. 1 H-NMR (CDCl3, 300MHz) δ (ppm): 0.69 (3H, s), 0.87 (3H, s), 0.90 (3H, s), 0.93 (3H, s), 1.18 (3H, s), 1.27( 3H, s), 2.34-2.45 (4H, m), 2.54-2.58 (1H, m), 2.91-2.92 (1H, m), 2.94 (1H, dd, J =3.3, 13.56 Hz), 4.30 (1H, d, J = 10.53 Hz), 4.40 (1H, d,...

Embodiment 3

[0092] 2-(Olean-12-en-28-oic acid benzyl ester-23-oxo[3,2-b]pyrazine)-carbonyl-benzoic acid

[0093] Referring to the synthetic method of 4-(olean-12-ene-28-acid benzyl ester-23-oxo[3,2-b]pyrazine)-4-oxo-butyric acid, by 23-hydroxy- Olean-12-ene-28-acid benzyl[3,2-b]pyrazine and phthalic anhydride were used as raw materials to synthesize the target object, and silica gel column chromatography (V 氯仿 :V 甲醇 = 50:1~20:1), a white solid was obtained with a yield of 55%. 1 H-NMR (CDCl3, 400 MHz) δ (ppm): 0.69 (3H, s), 0.89 (3H, s), 0.92 (3H, s), 0.93 (3H, s), 1.13 (3H, s), 1.30 (3H, s), 2.53-2.57 (1H, m), 2.94 (1H, dd, J = 3.3, 13.56 Hz), 2.94-2.98 (1H, m), 4.50-4.56 (2H, m), 5.07 (1H , d), 5.09 (1H, d), 5.36 (1H, t), 7.18 (1 H, m), 7.31-7.37 (5H, m), 7.35-7.38 (2 H, m), 7.68 (1 H, m), 8.19 (1 H, s), 8.44 (1 H, s).

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Abstract

The invention relates to the field of organic synthesis and medicinal chemistry and specifically relates to an alpha-hederagenin derivative with a structure as shown in a general formula I. The invention discloses a preparation method for the alpha-hederagenin derivative, drug compounds containing the alpha-hederagenin derivative and application thereof in tumor drug-resisting reversion.

Description

technical field [0001] The invention relates to the fields of organic synthesis and medicinal chemistry, in particular to a class of α-hedera saponin derivatives, a pharmaceutical composition containing them, a preparation method thereof and an application for reversing tumor drug resistance. [0002] technical background [0003] In recent years, the emergence of new anti-tumor drugs has made cancer treatment hopeful, but the ensuing drug resistance of tumors has become the biggest obstacle in the treatment of tumors. Tumor multidrug resistance (MDR) induced by chemical drugs makes it difficult for cancer patients to obtain sustained and effective therapeutic effects, which poses a severe challenge to modern cancer treatment and anti-tumor drug development. Therefore, the development of new compounds with new structures, low toxicity, and high-efficiency MDR reversal activity is a hot topic in the research of tumor therapeutics and pharmacology. [0004] Since natural produ...

Claims

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Application Information

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IPC IPC(8): C07J71/00A61K31/58A61P35/00
CPCY02P20/55C07J71/0047
Inventor 毕毅王洪波刘现轩杨延婷傅风华倪敬轩王晓马金波雷蕾
Owner YANTAI UNIV
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