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Bromo-norcantharidin ethyl gallate as well as preparation method and application thereof

A technology for methylcantharidin mono-ethyl ester and norcantharidin, which is applied to bromonorcantharidin mono-ethyl ester and its preparation method and application field, can solve problems such as no reports, and achieves low cost and purity High, high-yield effect

Active Publication Date: 2015-04-01
GUIZHOU BAIQIANG PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

ZL201410163619.4, ZL201410163711.0, ZL201410163705.5, etc. disclose the method for preparing demethylcantharidin acid salt, and the prior art also discloses a method for synthesizing 5,6-dibromonorcantharidin through bromine addition reaction, However, there is no report on the synthesis of ring-opened 5,6-dibromonorcantharidin monoester

Method used

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  • Bromo-norcantharidin ethyl gallate as well as preparation method and application thereof
  • Bromo-norcantharidin ethyl gallate as well as preparation method and application thereof
  • Bromo-norcantharidin ethyl gallate as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of embodiment 1 intermediate A, i.e. 5,6-dihydronorcantharidin: the reaction formula is as follows:

[0028]

[0029] Take out a certain amount of maleic anhydride from the reagent bottle, place it in a dry grinding body and grind it finely, then weigh 12.021g of the finely ground maleic anhydride with an electronic balance, put it in a dry three-necked flask, and plug it Stopper, add diethyl ether and stir, when the amount of diethyl ether is 90mL, the maleic anhydride is completely dissolved. After the maleic anhydride was completely dissolved, 13 mL of furan was slowly added through the dropping funnel for 13 minutes. The temperature was controlled to start the reaction at 38°C. After reacting for 1 h, white solids appeared in the solution, and the longer the time, the more white solids there were. After reacting for 24 hours, it was suction filtered to obtain white solid intermediate A, namely 5,6-dihydronorcantharidin. The dry weight is 17.459...

Embodiment 2

[0031] The preparation of embodiment 2 intermediate B, i.e. 5,6-dibromonorcantharidin: the reaction formula is as follows:

[0032]

[0033] Weigh 5 g of intermediate A obtained in Example 1, place it in a 250 mL two-necked flask, add 20 mL of chloroform and start stirring at room temperature until the reaction solution in the reaction system is stirred into a suspension. At this time, under stirring at room temperature, use a dropping funnel to add dropwise a mixture of 2.5 mL of chloroform and 0.5 mL of liquid bromine. After the addition is complete, rinse the dropping funnel with 2.5 mL of chloroform, and slowly add the rinse , Add the mixed solution and the rinse solution for a total of 20 minutes, and observe the phenomenon. After the reaction was completed, it was suction filtered and washed three times with carbon tetrachloride to obtain white solid intermediate B, namely 5,6-dibromonorcantharidin. The dry weight is 8.330g, and the yield is 85.35%. Melting point: 1...

Embodiment 35

[0034] The preparation of embodiment 35,6-dibromonorcantharidin monoacid ethyl ester: the reaction formula is as follows:

[0035]

[0036] Weigh 0.500g of the intermediate B obtained in Example 2, place it in a round bottom flask, add 1.5mL 95% ethanol, start stirring and raise the temperature to 78°C when the solution starts to reflux, then slowly add 95% ethanol drop by drop , until the solution became clear. Then suction filter while it is hot, seal the obtained filtrate, put it in the refrigerator, and start to crystallize. Overnight, the next day, a large number of white crystals appeared in the Erlenmeyer flask, which was filtered by suction to obtain a white solid, namely ethyl 5,6-dibromonorcantharidin monoate. The dry weight was 469mg, and the yield was 82%. Melting point: >240°C. Rf: 0.63 (developing solvent: petroleum ether: ethyl acetate = 10:1). 1 HNMR (DMSO-d6) δ: 12.64 (s, 1H), 4.77 (d, 2H), 4.41 (d, 1H), 4.01 (q, 2H), 3.34 (s, 2H), 3.21 (s, 1H), 1.13(t...

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Abstract

The invention discloses bromo-norcantharidin ethyl gallate, namely 5,6-dibromo norcantharidin ethyl gallate, wherein the structural formula of bromo-norcantharidin ethyl gallate is as shown in the formula I. As is proven by activity tests, bromo-norcantharidin ethyl gallate, namely open-cycle 5,6-dibromo norcantharidin ethyl gallate has a good anti-heptoma effect and can be used as an efficient and low-toxic cantharidin antineoplastic drug. The selectivity of a preparation process is good, raw materials are easy to obtain, the cost is low, the synthetic route is simple, the method is convenient to operate and conduct, toxicity of a product obtained through synthesis is low, the bromo-norcantharidin ethyl gallate is safe, the yield is high, and the purity is high. Therefore, the process has the characteristics of high efficiency, convenience and low cost.

Description

technical field [0001] The invention relates to bromonorcantharidin monoacid ethyl ester and a preparation method and application thereof, belonging to the field of cantharidin derivatives. Background technique [0002] Mylabris is a kind of insect body, which is a kind of folk traditional Chinese medicine in my country. A kind of cantharidin (cantharidin, C) extracted in the cantharidin 10 h 12 o 4 ) substances have a very special inhibitory effect on some cancers, and have a special inhibitory effect on ascites liver cancer or primary liver cancer, and have high medicinal value. [0003] Cantharidin can also be modified in structure to synthesize a lot of cantharidin derivatives, which greatly reduces the toxic and side effects and can better inhibit cancer. For example, demethylcantharidin or hydroxycantharidin, etc. have anti-cancer activity similar to cantharidin, and even the activity of cantharidin is lower in comparison. With the development of science and techn...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/08A61P35/00
CPCC07D493/08
Inventor 张云辉赵长阔张沛李晓飞
Owner GUIZHOU BAIQIANG PHARMA
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