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A tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group

A technology of amide group and tegafur, which is applied in the field of tegafur derivatives, can solve the problems of high toxicity and achieve the effects of reducing toxicity, improving curative effect and high yield

Inactive Publication Date: 2015-12-02
INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the compounds studied by the applicant have made progress, they still have relatively high toxicity and other deficiencies

Method used

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  • A tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group
  • A tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group
  • A tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group

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Embodiment 1

[0019] Embodiment 1: A kind of preparation method of tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group, the steps are as follows:

[0020] ①Dissolve 3-(methoxycarbonylmethyl)tegafur in methanol, then add sodium hydroxide solution dropwise, mix sodium hydroxide and distilled water at a weight-to-volume ratio of 1:20-30 to make a solution, 45 React at ℃ for 2-4 hours, evaporate the solvent under reduced pressure, extract with ethyl acetate and distilled water to separate the organic layer and water layer, extract and combine the organic layers with water, adjust the pH value to 4, then extract with ethyl acetate, combine the organic layers, Add anhydrous sodium sulfate to dry, filter, and evaporate the solvent to obtain 1-(tetrahydro-2-furyl)-3-acetoxy-5-fluoro-2,4-pyrimidinedione;

[0021] ②Take 1-(tetrahydro-2-furyl)-3-acetoxy-5-fluoro-2,4-pyrimidinedione and dioxane, mix them in a ratio of 1:3-4 by weight and volume, and then add chlorine The volume...

Embodiment 2

[0023] Embodiment 2: A kind of preparation method of tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group, the steps are as follows:

[0024] ①Put 6.8g of 3-(methoxycarbonylmethyl)tegafur into a reaction flask, add 10ml of methanol, heat to dissolve, dissolve 1.4g of sodium hydroxide in 35ml of distilled water, add the sodium hydroxide solution dropwise, React at 45°C for 3 hours, evaporate the solvent under reduced pressure, add 50ml of distilled water and 50ml of ethyl acetate to extract and separate the organic layer and the water layer, extract the organic layer with 50ml of water once, combine the water layers, and adjust the pH value to 4. Extract twice with 50ml of ethyl acetate, combine the organic layers, add 10g of anhydrous sodium sulfate to dry for 30 minutes, filter and evaporate the solvent to obtain 1-(tetrahydro-2-furyl)-3-acetoxy- 4.7g of 5-fluoro-2,4-pyrimidinedione, the yield is 73.4%;

[0025] ② Take 5.8g of 1-(tetrahydro-2-furyl)-3-...

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Abstract

The invention provides a tegafur derivative containing a 1,3,4-thiadiazole heterocyclic ring and an amide group. The structural formula of the tegafur derivative is as shown in the specification. A preparation method of the tegafur derivative comprises the steps of (1) dissolving a 3-(methoxycarbonylmethyl)tegafur in methanol, dropwise adding a sodium hydroxide solution, extracting by using ethyl acetate and distilled water and separating out an organic layer and a water layer, next, extracting by using ethyl acetate and blending the organic layers, and adding anhydrous sodium sulfate to obtain 1-(tetrahydro-2-furyl)-3-carbethoxy-5-fluoro-2,4-pyrimidinedione; (2) blending 1-(tetrahydro-2-furyl)-3-carbethoxy-5-fluoro-2,4-pyrimidinedione with dioxane, then adding sulfoxide chloride to obtain a 1-(tetrahydro-2-furyl)-3-chloracetyl-5-fluoro-2,4-pyrimidinedione solution, and then adding dioxane, evenly mixing and then sealing for later use; (3) taking 2-amino-5-p-nitrophenyl-1,3,4-thiadiazole, dioxane and triethylamine, and dropwise adding the 1-(tetrahydro-2-furyl)-3-chloracetyl-5-fluoro-2,4-pyrimidinedione solution obtained in the step (2) to obtain a pure product 1-(tetrahydro-2-furyl)-3-acetamido-[5-p-nitrophenyl-(1,3,4-thiadiazole-2-yl)]-5-fluoro-2,4-pyrimidinedione. The tegafur derivative has anti-tumor effect and no obvious toxicity, and is used for clinically treating malignant tumors.

Description

technical field [0001] The invention relates to a compound for inhibiting tumor cell proliferation, which is a tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide group. Background technique [0002] Since the incidence of malignant tumors is increasing year by year, drugs to inhibit tumors have become one of the important topics studied by technicians from all over the world. Among various tumor-inhibiting compounds, 5-fluorouracil (5-Fu) is a relatively effective and safe compound, which is widely used in the treatment of various cancers. After years of clinical drug statistics, it shows that although it inhibits the proliferation of tumor cells by interfering with and blocking the synthesis of DNA, RNA and protein, 5-Fu has a short half-life and can only be administered intravenously or arterially. relatively bigger. For this reason, those skilled in the art have been studying a tegafur derivative containing 1,3,4-thiadiazole heterocycle and amide grou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D417/14A61K31/513A61P35/00
CPCC07D417/14
Inventor 刘爱芹秦三海于胜海孙敬勇吴忠玉卢霞王延风王风玲李慧金
Owner INST OF PHARMACY SHANDONG PROV ACAD OF MEDICAL SCI
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