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5-fluorouracil furane derivative and preparation method thereof

A technology of fluorouracil furan and fluorouracil, which is applied in the field of anticancer prodrug 5-fluorouracil furan derivatives and its preparation, and can solve the problems of many adverse reactions, short half-life, and limited application

Inactive Publication Date: 2018-12-28
HEZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, 5-fluorouracil has obvious first-pass metabolism, short half-life, weak lipophilicity, unstable oral absorption, close therapeutic dose and toxic dose, and many adverse reactions in clinical application, which limit its further application.

Method used

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  • 5-fluorouracil furane derivative and preparation method thereof
  • 5-fluorouracil furane derivative and preparation method thereof
  • 5-fluorouracil furane derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 0.56g of 5-fluorouracil and 2ml of aqueous formaldehyde (36%) were added to a 25ml one-necked flask, heated to 60°C for 6 hours, and then distilled under reduced pressure to obtain a colorless viscous liquid (intermediate A).

[0024] 0.676g of 2-furancarboxylic acid was added to 5ml of thionyl chloride, heated to reflux for 5 hours, and the excess thionyl chloride was distilled off under reduced pressure to obtain an intermediate for future use (intermediate B).

[0025] Intermediate B was dissolved in 15ml of anhydrous acetonitrile, cooled in an ice bath, 1.5ml of triethylamine was added, and then 10ml of acetonitrile solution of intermediate A was slowly added dropwise. After the addition was complete, the reaction was carried out at room temperature for 24 hours. Evaporate the solvent under reduced pressure, add 50ml of ethyl acetate to dissolve, wash with 30ml of 10% aqueous sodium carbonate solution, 30ml of saturated saline successively, dry over anhydrous sodium ...

Embodiment 2

[0027] 0.56g of 5-fluorouracil and 2ml of aqueous formaldehyde (36%) were added to a 25ml one-necked flask, heated to 60°C for 6 hours, and then distilled under reduced pressure to obtain a colorless viscous liquid (intermediate A).

[0028] Add 0.676g of 2-furancarboxylic acid to 25ml of anhydrous acetonitrile, add 0.828g of N-hydroxysuccinimide in ice bath, add 1.86g of dicyclohexylcarbodiimide, react at room temperature for 2 hours, then slowly add The acetonitrile solution of intermediate A was 10ml, and 1.5ml of triethylamine was added, and the addition was completed, and the reaction was carried out at room temperature for 24 hours. Filtrate, filtrate, evaporate solvent under reduced pressure, add 50ml ethyl acetate to dissolve, wash successively with 10% sodium carbonate aqueous solution 30ml, saturated saline 30ml, dry over anhydrous sodium sulfate, obtain crude product by distillation under reduced pressure, silica gel column chromatography ( Petroleum ether: ethyl ac...

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Abstract

The invention relates to a 5-fluorouracil furane derivative and a preparation method thereof. The structural formula of the 5-fluorouracil furane derivative is shown in the description. According to the 5-fluorouracil furane derivative and the preparation method thereof, 5-fluorouracil reacts with formaldehyde to obtain hydroxymethyl 5-fluorouracil; 2-furoic acid reacts with an active compound toobtain a reactive intermediate, then the reactive intermediate reacts with hydroxymethyl 5-fluorouracil to obtain a 5-fluorouracil anticancer pro-drug. The 5-fluorouracil furane derivative and the preparation method thereof have the advantages that the reaction steps of the synthetic route are few, the reaction conditions are mild, the reactive raw materials are simple and easily obtained, and theproduct yield is higher.

Description

technical field [0001] The invention relates to an anticancer prodrug 5-fluorouracil furan derivative and a preparation method thereof Background technique [0002] In February 2017, the National Cancer Center released the latest cancer data in China, showing that in China, there are 4.29 million new cancer cases each year, accounting for 20% of the new cases in the world. Cancer prevention and treatment has become an important public health issue in my country. In recent decades, 5-fluorouracil has been used as the preferred anti-tumor metabolic drug for the clinical treatment of various cancers such as esophageal cancer, gastric cancer, colon cancer, ovarian cancer, cervical cancer, lung cancer and breast cancer. However, 5-fluorouracil has obvious first-pass metabolism, short half-life, weak lipophilicity, unstable oral absorption, close therapeutic dose and toxic dose, and many adverse reactions in clinical application, which limit its further application. Over the year...

Claims

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Application Information

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IPC IPC(8): C07D405/12
CPCC07D405/12
Inventor 严小威王素娟任爱山钟星朱东建胡彩霞
Owner HEZHOU UNIV
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