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Anti-tumor compound and preparation thereof

A compound and anti-tumor technology, which is applied in the field of anti-tumor, can solve the problems of poor absorption and poor fat solubility, and achieve the effects of facilitating absorption, reducing the incidence and degree of occurrence, and reducing the number of administrations and dosages

Inactive Publication Date: 2009-05-27
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It is clinically used to treat liver cancer, gastric cancer, lung cancer, breast cancer, etc., but because of its poor fat solubility, it is not easy to absorb, and it is often administered clinically by injection

Method used

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  • Anti-tumor compound and preparation thereof
  • Anti-tumor compound and preparation thereof
  • Anti-tumor compound and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1) Synthesis of 5'-trityl fluorouridine:

[0026] In a three-necked flask equipped with a thermometer, add 0.98g (0.004mol) of floxuridine and 20ml of pyridine, stir to dissolve them, then add 1.56g (0.0056mol) of triphenylmethyl chloride and a catalytic amount of 4-bis Aminopyridine. The reaction mixture was in N 2 Stir the reaction at room temperature under protection for 12 hours, heat to 100°C for 3 hours, cool to room temperature, pour into about 100ml of ice water, and extract 3 times with ethyl acetate (40ml×3), the obtained organic phase is sequentially washed with 2mol / L hydrochloric acid , water, saturated NaHCO 3 solution, washed with saturated NaCl solution, and the resulting organic phase was dried over anhydrous sodium sulfate. After filtration and recovery of the organic solvent, the resulting residue was separated by silica gel column chromatography [chloroform:methanol (V / V)=20:1] to obtain 0.85 g of a white solid which was 5′-tritylfluridine. The m...

Embodiment 2

[0032] 1) Synthesis of 5'-trityl fluorouridine:

[0033] In a three-necked flask equipped with a thermometer, add 1.34g (0.0054mol) of floxuridine and 25ml of triethylamine, stir to dissolve them, then add 3.45g (0.012mol) of triphenylmethyl chloride and a catalytic amount of 4 - Dimethylaminopyridine. The reaction mixture was in N 2 Stir the reaction at room temperature under protection for 12 hours, heat to 70°C for 3 hours, cool to room temperature, pour into about 100ml of ice water, and extract 3 times with chloroform (40ml×3), the obtained organic phase is sequentially washed with 2mol / L hydrochloric acid, water , saturated NaHCO 3 solution, washed with saturated NaCl solution, and the resulting organic phase was dried over anhydrous sodium sulfate. After filtration and recovery of the organic solvent, the obtained residue was separated by silica gel column chromatography [chloroform:methanol (V / V)=20:1] to obtain 1.08 g of white solid which was 5′-tritylfluridine. T...

Embodiment 3

[0039] 1) Synthesis of 5'-trityl fluorouridine:

[0040] In a three-necked flask equipped with a thermometer, add 1.12g (0.0046mol) of floxuridine, 15ml of triethylamine, and 12ml of diisopropylethylamine, stir to dissolve them, and then add 4.36g (0.0157mol) of triphenyl methyl chloride and a catalytic amount of 4-dimethylaminopyridine. The reaction mixture was in N 2 Stirring reaction at room temperature under protection for 12h, heating to 80°C for 3h, cooling to room temperature, pouring into 100ml of ice water, and extracting 3 times with 1,-dichloroethane (40ml×3), the obtained organic phase was successively washed with 2mol / L hydrochloric acid, water, saturated NaHCO 3 solution, washed with saturated NaCl solution, and the resulting organic phase was dried over anhydrous sodium sulfate. After filtration and recovery of the organic solvent, the resulting residue was separated by silica gel column chromatography [chloroform:methanol (V / V)=20:1] to obtain 1.20 g of a w...

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Abstract

The invention provides an anti-tumor compound and a method for preparing the same. The method for preparing the anti-tumor compound (3'-{4-[3-(3, 5-di-t-butyl-4-methoxyphenyl)-3-keto-1-propenyl] benzoyl} floxuridine (BOBA-3'- floxuridine ester)) adopts a three-step method of selective protection, esterification and deprotection for synthesis. Compared with floxuridine, BOBA-3'- floxuridine ester has the advantages of prolonging half decay time of the floxuridine, improving fat soluble property of the floxuridine, reducing administration frequency and administration dosage as well as probability and degree of causing adverse reactions; and under the action of in vivo esterase, the BOBA-3'- floxuridine ester can be hydrolyzed into BOBA and the floxuridine, so that the double functional anti-tumor drug which can not only resist metabolism but also induce tumor cells to break up.

Description

technical field [0001] The invention belongs to the field of anti-tumor technology, in particular to an anti-tumor compound and a preparation method thereof. Background technique [0002] Tumor is a common and frequently-occurring disease that seriously threatens human health. Humans have a high probability of dying from malignant tumors, and its mortality rate is second only to cardiovascular and cerebrovascular diseases, ranking second among all disease mortality rates. At present, the treatment methods for tumors are still traditional surgery, radiation therapy and drug therapy, but to a large extent, drug therapy is still the main method. Antineoplastic drugs can be roughly divided into three categories according to the principle of action: (1) drugs that directly act on DNA and destroy its structure and function; (2) drugs that interfere with DNA and nucleic acid synthesis; (3) drugs that affect protein synthesis. [0003] In recent years, with the progress of molecula...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H19/073A61K31/7072A61P35/00
Inventor 张三奇陈建刚靳菊情单爱林杨广德
Owner XI AN JIAOTONG UNIV
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