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Fluorouracil compound, and preparation method and application thereof

A technology of fluorouracil compounds, applied in the field of fluorouracil compounds, their preparation and application, to achieve the effect of simple and feasible route preparation method

Active Publication Date: 2013-08-07
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Based on the analysis of the current research status, combining fluorouracil and triazole to design a series of new derivatives provides the possibility for the development of new drugs, and there are no relevant literature reports so far.

Method used

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  • Fluorouracil compound, and preparation method and application thereof
  • Fluorouracil compound, and preparation method and application thereof
  • Fluorouracil compound, and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Preparation of 1-(5′-deoxy-β-D-ribofuranose)-3-(3′-p-fluorobenzyl-1′,2′,3′-triazolyl)-methylene-5-fluorouracil (compound Ⅰ-1 ）

[0051] Add 1-(5′-deoxy-β-D-ribofuranose)-5-fluorouracil (8.1mmol, 2g), DMF (20ml), K 2 CO 3 (28.9mmol, 4g), propyne bromide (24.3mmol, 1.9ml), stirred at room temperature, and reacted for 3-5 hours until TLC (254nm, petroleum ether: acetone = 1:1) detected that the raw materials were consumed. After the reaction is completed, add 15ml of distilled water, extract with ethyl acetate (15ml×2), combine the ethyl ester phases, dry with 4g of magnesium sulfate for 3 hours, and vacuum-filter and then rotary evaporate for 40 to obtain a yellow solid, weigh 2.2g after vacuum drying, and set aside. Yield 95.7%.

[0052] Add the above-prepared compound (0.7mmol, 200mg), the mixed solution of tert-butanol and water (9ml, tert-butanol / water=8 / 1), Cu (2.8mmol, 179mg) and CuSO 4 (0.7mmol, 124mg), p-fluorobenzyl azide (2.1mmol, 317mg), react at 50°C fo...

Embodiment 2

[0054] Compounds I-2 to I-15 were synthesized with reference to Example 1, and the corresponding aromatic methyl azides were used in step (2).

Embodiment 3

[0056] Synthesis of compound II-1

[0057] Take the compound 1-(2',3'-O-isopropylidene-5'-p-toluenesulfonyl-β-D-ribofuranose)-5-fluorouridine (6.6g, 17mmol) in a 250mL round bottom Into the flask, add acetonitrile 100mL, potassium carbonate (24g, 17mmol), propyne bromide (4mL, 51mmol), stir at room temperature, and react for 5h, TLC (V petroleum ether: V acetone = 3:1) detects that the reaction of raw materials is complete, stop reaction. Diatomaceous earth filter aid, ethyl acetate washed the filter cake, combined organic phase, rotary steamed, added ethyl acetate 80mL, washed with distilled water three times, added magnesium sulfate to dry, suction filtered and rotary steamed to obtain a white solid, weighing 6.3g, Yield 82%, standby.

[0058] Take the compound obtained above (0.297g, 0.66mmol) and place it in a 25mL round bottom flask, add 8mL of tert-butanol and 1mL of water as a mixed solvent, add copper powder (0.128g, 2.0mmol) and copper sulfate (0.083g, 0.33mmol) ...

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Abstract

The invention discloses series of compounds of fluorouracil in 1- or 3-triazole rings and a preparation method of compounds, belongs to the field of medicinal chemistry, and particularly relates to a novel fluorouracil antitumor compound with the following general formula of chemical structure. The fluorouracil compound has antitumor activity; and the preparation method is economical, simple, mild and efficient.

Description

technical field [0001] The invention relates to the field of medicinal chemistry, in particular to novel fluorouracil triazole compounds 1-(5'-R 1 -β-D-ribofuranose)-3-(3'-arylalkyl-1',2',3'-triazolyl)-methylene-5-fluorouracil, 1-(2',3' -Dioxy-propylidene-5'-R 1 -β-D-ribofuranose)-3-(3'-arylalkyl-1',2',3'-triazolyl)-methylene-5-fluorouracil, 1-(2',3' -Dioxy-propylidene-5'-(4'-R 3 -1′-1′,2′,3′-triazolyl)-methylene-β-D-ribofuranose)-5-fluorouracil compounds, 1-(2′,3′,5′-O -Triacetyl-β-D-ribofuranose)-3-(3'-arylalkyl-1',2',3'-triazolyl)-methylene-5-fluorouracil compounds and preparation methods and its application. Background technique [0002] Over the years, scholars at home and abroad have made various modifications to the structure of 5-Fu, and have studied the toxicology, pharmacology, and metabolism of the modified products, such as introducing small molecule amino acids, short peptides, glucose, glycerol, etc. into its structure. Modified phospholipids; bonded with...

Claims

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Application Information

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IPC IPC(8): C07H19/09C07H1/00A61K31/7072A61P35/00
Inventor 吴春丽李杰明魏会杰蒋月明杭晔陈新丽朱凯乔家彬
Owner ZHENGZHOU UNIV
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