Semisynthesis method of antineoplastic activity natural product peperomin E

A technology for antitumor activity and oxaliphacin is applied in the field of semi-synthesis of antitumor active natural product oxalicum E, which can solve the problems of high cost, low content, poor product purity and the like, achieve mild conditions, expand sources and simple methods Effect

Inactive Publication Date: 2014-08-06
NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, Herbapironin E can only be obtained from the medicinal material of Shichancao through traditional separation and purification methods. Because the content of this compound in the medicinal material is very low, it cannot even be detected in some medicinal materials from some origins, and the separation and purification methods are complicated and costly. High, poor product purity, which has become an important factor restricting its in-depth research, while restricting the further pharmaceutical research of this anti-tumor lead compound

Method used

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  • Semisynthesis method of antineoplastic activity natural product peperomin E
  • Semisynthesis method of antineoplastic activity natural product peperomin E
  • Semisynthesis method of antineoplastic activity natural product peperomin E

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] (3 R , 4 R )-2-Phenylselenyl oxalonine A (II) preparation

[0021] Dissolve boronine A (I) (5g, 12mmol) in triethylamine (22.5mL, 162mmol), stir at 0°C for 10min, add trimethylsilyl trifluoromethanesulfonate (25mL, 138mmol), continue After stirring at 0°C for 40min, add a chloroform solution (50mL) containing phenylselenyl chloride (9.5g, 50.0mmol) and stir at 0°C for 30min. 2 Carried out under gas protection. After adding 500mL of saturated ammonium chloride solution to the reaction solution, extract it with ethyl acetate (800mL) for 3 times, combine the extracts, recover ethyl acetate, perform silica gel column chromatography [200-300 mesh silica gel, petroleum ether-ethyl acetate ( Volume ratio 4:1)] refined to get (3 R , 4 R )-2-Phenylselenoylporonin A(II) (5.95g, 87% yield): m.p. 77-79 o C; [α] 20 D +50.1 (c 0.40, CHCl 3 ); ESI-MS m / z 593.0676 [M+Na] + , 1 H-NMR δ H 7.60(2H, m, m -PhSe), 7.39(1H, m, p -PhSe), 7.29(2H, m, o -PhSe), 6.45(1H, br...

Embodiment 2

[0025] (3 R , 4 R )-2-Phenylselenyl oxalonine A (II) preparation

[0026] Dissolve boronine A (I) (15g, 36mmol) in triethylamine (70mL, 0.50mol), stir at 0°C for 10min, then add trimethylsilyl trifluoromethanesulfonate (80mL, 0.44mol), After continuing to stir at 0°C for 40 min, add a chloroform solution (150 mL) containing phenylselenyl chloride (30 g, 0.16 mol) and stir at 0°C for 30 min. 2 Carried out under gas protection. After adding 1000mL saturated ammonium chloride solution to the reaction solution, extract it with ethyl acetate (1.5L) for 3 times, combine the extracts, recover ethyl acetate, perform silica gel column chromatography [200-300 mesh silica gel, petroleum ether-ethyl acetate (volume ratio 4:1)] refined to get (3 R , 4 R )-2-Phenylselenoylporonin A(II) (16.9 g, yield 82.4%).

[0027] Preparation of Herbaperine E(III)

[0028] Will (3 R , 4 R )-2-Phenylselenoylpiperonin A(II) (10g, 18mmol) was dissolved in tetrahydrofuran (180mL), added glacial acet...

Embodiment 3

[0030] (3 R , 4 R )-2-Phenylselenyl oxalonine A (II) preparation

[0031] Dissolve boronine A (I) (200g, 0.48mol) in triethylamine (1000mL, 7.2mol), stir at 0°C for 20min, then add trimethylsilyl trifluoromethanesulfonate (1000mL, 5.5mol) , after continuing to stir at 0°C for 40min, add a chloroform solution (1000mL) containing phenylselenyl chloride (400g, 2.08mol), and stir at 0°C for 40min. 2 Carried out under gas protection. After adding 8 L of saturated ammonium chloride solution to the reaction solution, extract it three times with ethyl acetate (10 L), combine the extracts, recover ethyl acetate, perform silica gel column chromatography [200-300 mesh silica gel, petroleum ether-ethyl acetate (volume ratio 4:1)] refined to get (3 R , 4 R )-2-Phenylselenoylporonin A(II) (219.2 g, yield 80.1%).

[0032] Preparation of Herbaperine E(III)

[0033] Will (3 R , 4 R )-2-Phenylselenoylpiperonin A(II) (100 g, 0.18mol) was dissolved in tetrahydrofuran (1000m L), added gla...

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Abstract

A semisynthesis method of an antineoplastic activity natural product peperomin E relates to a semisynthesis method of the natural product peperomin E having antineoplastic activity. A peperomin A extracted from a whole peperomia blanda of traditional Chinese medicines is taken as a raw material, the two steps of benzeneselenenylnucleophilic substitution and oxidationde-benzene-seleno are carried out to obtain the peperomin E, and the high-quality peperomin E of which the purity is more than 99.0% is obtained through column chromatography on a silica gel.

Description

technical field [0001] The invention belongs to the field of drug synthesis, and relates to a semi-synthetic method of a natural product with anti-tumor activity, boronin E. Background technique [0002] Grass piperonine E is derived from the anti-tumor traditional Chinese medicine Shichancao ( Peperomia dindygulensis Miq.) found in α -Methylene- gamma - Lignans with butyrolactone ring (JL Wu, N Li, T Hasegawa, et al .Bioactive secolignans from Peperomia dindygulensis . Journal of Natural Products, 2006, 69: 790-794), the structural formula is as follows: [0003] [0004] Studies have found that lignan compounds have varying degrees of inhibitory effect on tumor cell proliferation, among them, the one represented by cyperonin E contains α -Methylene- gamma Compounds with -butyrolactone ring group are the most active. In vitro activity studies have shown that the effect of grass piperonine E on human lung cancer cell lines WI-38, VA-13 and A549, human breast ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D407/14
CPCC07D407/14
Inventor 王欣之王天麟文红梅李伟杨帆刘睿
Owner NANJING UNIVERSITY OF TRADITIONAL CHINESE MEDICINE
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