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Rapid and safe preparation method of triptolide triol

A fast and rapid technology for triptolide, applied in the field of rapid and safe preparation of triptolide triol, can solve the problems of triptolide triol failure to be popularized and applied, dangerous immune toxicity and reproductive toxicity, product and by-product toxicity, etc. problems, achieve the effects of shortening the reaction cycle, stabilizing the controllability of the reaction, and stabilizing the reaction conditions

Active Publication Date: 2018-10-16
GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] In this preparation method, the reaction time is shortened by nearly half (from 1 week to 96 hours), but, for industrial production, the reaction time of 96h is still too long
And, in this preparation method, in the purification process (extraction, column chromatography etc.) reaction liquid still very easily splashes to experiment bench and human body, very dangerous (because residual raw material triptolide has extremely strong immunotoxicity and reproductive toxicity, products and by-products also have certain toxicity)
Therefore, triptolide triol has not been promoted and applied so far.

Method used

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  • Rapid and safe preparation method of triptolide triol
  • Rapid and safe preparation method of triptolide triol
  • Rapid and safe preparation method of triptolide triol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038]

[0039] Weigh about 0.8 g of sodium dihydrogen phosphate, add 500 mL of ultrapure water to dissolve it, and add a phosphoric acid solution with a volume fraction of 1% at room temperature to adjust the pH to 4.0 to obtain a phosphate buffer solution with a pH of 4.

[0040] Take 0.5 g of triptolide and place it in a 20 mL microwave reaction bottle, add 10 mL of the prepared phosphate buffer solution to dissolve, and seal it. Make it fully mixed, and set 140°C to react for 1.5h. After the reaction, the reaction solution was a yellow solution. The mother liquor of the compound represented by formula (I) is obtained.

[0041] Place the reacted yellow solution on a rotary evaporator to quickly drain the solvent, add methanol to redissolve the residual solid, pipette the redissolved product into a centrifuge tube, and after high-speed centrifugation, pipette the supernatant to the front for fixation A syringe tube with a 0.22μm filter membrane, slowly filtered into an ...

Embodiment 2

[0068]

[0069] The microwave heating conditions were set at 155°C, the reaction time was 40min, and the phosphate buffer solution was adjusted to pH=3.5. The rest of the operations were the same as in Example 1. Finally, 266.8 mg of triptolide triol was obtained with a yield of 50.82%. The purity is 98.3%, and the remaining structural test data are the same as in Example 1.

Embodiment 3

[0071]

[0072] Weigh NaH 2 PO 4 ·H 2 O 27.6g, dissolved in distilled water to 1000mL. Configured as a solution. Weigh Na 2 HPO 4 2H 2 O 35.6g was added to distilled water to dissolve in 1000mL, and prepared as liquid B. Take 5.3 mL of solution A and 94.7 mL of solution B and mix to obtain a phosphate buffer solution with pH=8.0.

[0073] Put 0.5 g of triptolide into a 20 mL microwave reaction bottle, add 10 mL of the prepared phosphate buffer solution of pH=8.0 to dissolve, and seal it. Make it well mixed, set 160°C for 25min. After the reaction, the reaction solution was a yellow solution. The mother liquor of the compound represented by formula (I) is obtained.

[0074] The reacted yellow solution was frozen, and the solvent was sucked dry with a freeze dryer to obtain a yellow powder. All the other operations are the same as in Example 1. 282.3 g of triptolide triol was obtained with a yield of 53.77%. The remaining structural test data are the same as in E...

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Abstract

The invention discloses a quick and safe preparation method of triptriolide (a structure is as shown in a formula (I)). The quick and safe preparation method specifically comprises the following steps of, in a phosphoric acid buffer solution with pH (potential of Hydrogen) of 3.0 to 5.0 or pH of 7.0 to 9.0, using a compound as shown in a formula (II) as a raw material, heating the compound to 120 to 160 DEG C in a microwave manner in a closed environment to carry out a hydrolysis reaction for 25min to 6h, so as to obtain the triptriolide. According to the preparation method provided by the invention, the phosphoric acid buffer solution is used as reaction medium; a microwave heating device with pressure bearing protection is used as a reaction vessel; the preparation method merely has one synthesis step, further, only needs a reaction time of 25min to 6h, and has advantages of being safe, and being short in reaction period, stable in reaction condition, easy to operate and higher in yield, and the like; the popularization and the application of the compound of the formula (I) are facilitated.

Description

technical field [0001] The invention relates to a fast and safe preparation method of triptolide triol. Background technique [0002] As early as 1989, people such as Ma Pengcheng studied the separation and structure of triptolide triol, and disclosed the preparation method of this compound in the Chinese invention patent of application number 89106941.0 (publication number: CN1050021A) (see Example for details 4), including the following steps: 20 mg of triptolide was dissolved in 10 mL of methanol, and 5 mL of distilled water, 5 mL of phosphate buffer (pH 7.4) and 20 μL of NHEt were added 2 , placed for 1 week after stirring at room temperature. [0003] In this preparation method, the reaction time is too long, so that this compound has not received more attention and in-depth research in the following 10 years. [0004] Until 2002, another preparation method of triptolide triol was disclosed in PCT application with publication number WO 02 / 070472: adding 1.5 g of NaH t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J73/00
CPCC07J73/003
Inventor 刘博刘旭生徐鹏周文韩晓东毛炜徐方方刘敬功李援朝杨祎琦邓金宝邓远辉吴利兰田瑞敏陆金健张玉琴
Owner GUANGDONG HOSPITAL OF TRADITIONAL CHINESE MEDICINE
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