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Manufacturing method for deoxypodophyllotoxin

A technology of deoxypodophyllotoxin and podophyllotoxin, which is applied in the field of natural medicine and chemical medicine, can solve the problems of high energy consumption of deoxypodophyllotoxin, potential safety hazards, increased funds, etc., and is suitable for industrial production and increases risks Coefficients, preparation of simple effects

Active Publication Date: 2012-08-15
ZHEJIANG JIANFENG PHARM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In CN 101497618 and US 6284789, podophyllotoxin is converted into deoxypodophyllotoxin by hydrogen and palladium carbon reduction. The main disadvantage of this method is that high pressure must be used in production, and flammability Gas hydrogen, which has brought safety hazards in the production process, and the preparation of deoxypodophyllotoxin by this method requires high energy consumption and low yield, which greatly increases the capital required for production.

Method used

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  • Manufacturing method for deoxypodophyllotoxin
  • Manufacturing method for deoxypodophyllotoxin

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 1.0g podophyllotoxin and 0.91g NaBH to a 50ml single-neck bottle 4 , then add 25ml of anhydrous tetrahydrofuran; slowly add 15ml of CF 3 After the addition of COOH is complete, the temperature is raised to 70°C, and the reaction is completed for about 20 minutes. The reaction solution was poured into 100 ml of water, extracted three times with 10 ml of ethyl acetate, and the organic layer was separated. The organic layer was washed with 50 ml of saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the crude deoxypodophyllotoxin, which was then recrystallized from a mixed solvent of ethyl acetate:methanol=1:6 to obtain pure deoxypodophyllotoxin with a purity of 99.2% and a yield of 80%. White crystalline powder, mp 165~167℃;

[0024] UV: In methanol solution, λmax 292.1, 204.3nm is the characteristic absorption of the B band and K band of the substituted benzene ring;

[0025] IR: 1589, 1506, 1483cm-1:...

Embodiment 2

[0029] Add 1.0g podophyllotoxin, 1.0g NaBH to a 50ml single-neck bottle 4 , then add 25ml anhydrous tetrahydrofuran; slowly add 20ml CF 3 COOH, after the dropwise addition was completed, the temperature was raised to 50°C, and the reaction was completed for about 2 hours. The reaction solution was poured into 100 ml of water, extracted three times with 10 ml of ethyl acetate, and the organic layer was separated. The organic layer was washed with 50 ml of saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the crude deoxypodophyllotoxin, which was then recrystallized from a mixed solvent of ethyl acetate:methanol=1:10 to obtain pure deoxypodophyllotoxin with a purity of 98.2%, and the yield was 82%.

Embodiment 3

[0031] Add 1.0g podophyllotoxin, 1.20g NaBH to a 50ml single-neck bottle 4 , then add 25ml anhydrous tetrahydrofuran; slowly add 25ml CF 3COOH, after the dropwise addition is complete, react at room temperature, react for about 72 hours, and the reaction is complete. The reaction solution was poured into 100 ml of water, extracted three times with 10 ml of ethyl acetate, and the organic layer was separated. The organic layer was washed with 50 ml of saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain the crude deoxypodophyllotoxin, which was then recrystallized from a mixed solvent of ethyl acetate:methanol=1:4 to obtain the pure deoxypodophyllotoxin with a purity of 99.1% and a yield of 73%.

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Abstract

The invention relates to the field of natural drugs and chemical drugs, in particular to a manufacturing method for deoxypodophyllotoxin. The manufacturing method provided by the invention has the characteristics that the deoxypodophyllotoxin can be obtained through the reaction of podophyllotoxin with NaBH4 and CF3COOH, namely, podophylotoxin is reduced to deoxypodophyllotoxin by addition of with a reducing reagent and protonic acid. According to the invention, the applied materials have wide source and low price, so that the manufacturing method is applicable in industrial production.

Description

technical field [0001] The invention relates to the fields of natural medicines and chemical medicines, in particular to a preparation method of deoxypodophyllotoxin. Background technique [0002] Deoxypodophyllotoxin (DPT for short) is a compound extracted and purified from lignin plants. Chemical name: 5R-5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)furan(3',4':6,7)naphtho-[2,3- d]-1,3-dioxin-6(5aH)-one, the structural formula is as follows: [0003] [0004] Since the 1990s, pharmacological experiments have been reported to prove that DPT has an in vitro inhibitory effect on cell lines of P-388 leukemia, human lung cancer A-549 and colon cancer HT-29 (Arch Pharm (Weinheim). 1994 Mar; 327 (3 ): 157-9. PlataMed. 1993 June; 59 (3): 246-9), but only stays in the stage of in vitro activity test. The main reason why there is no experimental report of in vivo activity for more than ten years is that the compound is insoluble in water and cannot be made into preparations f...

Claims

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Application Information

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IPC IPC(8): C07D493/04
Inventor 朱雄黄金龙张仕金徐云根袁铎殷之武
Owner ZHEJIANG JIANFENG PHARM CO LTD
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