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5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative and preparation method thereof

A technology of fluorouracil and methoxycarboxyalkane, which is applied in the field of 5-fluorouracil-1-methoxycarboxyalkyl cyclodextrin derivatives and their preparation, can solve the problems of limited effect of reducing toxic and side effects and the like

Active Publication Date: 2021-06-11
NINGXIA MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] In view of this, the present invention provides a 5-fluorouracil-1-methoxycarboxyalkyl-type cyclodextrin derivative and a preparation method thereof, so as to solve the problem of reducing the toxic and side effects of drugs by simple combined medication in the prior art Limited, unable to make the drug exert a certain sustained release and targeting effect, and technical problems of releasing the original drug 5-fluorouracil based on the prodrug

Method used

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  • 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative and preparation method thereof
  • 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative and preparation method thereof
  • 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative and preparation method thereof

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Embodiment 1

[0056] S1: Add 1.3g (10mmol) of 5-fluorouracil and 1.8g (22.2mmol) of formaldehyde (37% purity) solution into a 50mL single-necked flask, and stir with a magnetic stirrer to fully mix the reaction solution and maintain the reaction The temperature is 60°C, and the reaction is 4 hours to obtain the mixed solution A. The mixed solution A in the single-necked flask is rotated by a rotary evaporator to remove the formaldehyde in the mixed solution A, and then the single-necked flask is dried in a vacuum oven. After 12 hours, 1-hydroxymethyl 5-fluorouracil was obtained as a transparent viscous substance.

[0057] S2: Add 10 mL of anhydrous acetonitrile to the 1-hydroxymethyl 5-fluorouracil prepared in step S1, and start stirring until the 1-hydroxymethyl 5-fluorouracil is completely dissolved. - After the fluorouracil is completely dissolved, add 1.281g (12.8mmol) of succinic anhydride and 0.066g (0.54mmol) of catalyst DMAP, keep the reaction temperature at 50°C, and react for 24h ...

Embodiment 2

[0070] S1: Add 1.3g (10mmol) of 5-fluorouracil and 1.8g (22.2mmol) of formaldehyde (37% purity) solution into a 50mL single-necked flask, and stir with a magnetic stirrer to fully mix the reaction solution and maintain the reaction The temperature is 60°C, and the reaction is 4 hours to obtain the mixed solution A. The mixed solution A in the single-necked flask is rotated by a rotary evaporator to remove the formaldehyde in the mixed solution A, and then the single-necked flask is dried in a vacuum oven. After 12 hours, 1-hydroxymethyl 5-fluorouracil was obtained as a transparent viscous substance.

[0071] S2: Add 10 mL of anhydrous acetonitrile to the 1-hydroxymethyl 5-fluorouracil prepared in step S1, and start stirring until the 1-hydroxymethyl 5-fluorouracil is completely dissolved. - After the fluorouracil is completely dissolved, add 1.281g (12.8mmol) of succinic anhydride and 0.066g (0.54mmol) of catalyst DMAP, keep the reaction temperature at 50°C, and react for 24h ...

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Abstract

The invention provides a 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative and a preparation method thereof, and belongs to the technical field of organic synthesis. The 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative is prepared from 5-fluorouracil, formaldehyde, alkyl dianhydride, N, N-carbonyl diimidazole and cyclodextrin as raw materials, the reaction process is simple in step operation, As a prodrug of 5-fluorouracil, the synthesized 5-fluorouracil-1-methoxycarboxy alkyl cyclodextrin derivative can improve the in-vivo dynamic process of the drug and increase the stability of the drug; and the 5-fluorouracine-1-methoxyl carboxy alkyl cyclodextrin derivative is not degraded in simulated stomach and small intestine liquid, but is degraded by specific enzyme in simulated blind colon liquid to release the raw medicine 5-fluorouracil (5-FU), so that the aim of colon targeted release of the raw medicine is achieved, the targeting property of the medicine is increased, the medicine effect is improved, and the toxic and side effects of gastrointestinal tracts are reduced.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and specifically relates to a 5-fluorouracil-1-methoxycarboxyalkyl type cyclodextrin derivative and a preparation method thereof. Background technique [0002] 5-fluorouracil (5-Fluorouracil, 5-FU), also known as fluorouracil, the chemical formula is C 4 h 3 FN 2 o 2 , is a pyrimidine analog, which is white or off-white crystal or crystalline powder, slightly soluble in water, slightly soluble in ethanol, almost insoluble in chloroform; dissolved in dilute hydrochloric acid or sodium hydroxide solution. As a fluoride of pyrimidines, 5-fluorouracil belongs to anti-metabolism and anti-tumor drugs, which can inhibit thymidine nucleotide synthase, block the conversion of deoxypyrimidine nucleotides into thymidine nucleosides, and interfere with DNA synthesis. It also has a certain inhibitory effect on RNA synthesis. A pyrimidine-like spectrum, pyrimidine nucleotide synthetase. The mech...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08B37/16A61K47/61A61K31/513A61P1/00A61P35/00
CPCC08B37/0012A61K47/61A61K31/513A61P1/00A61P35/00
Inventor 王志忠魏世杰黄青闫春华马姜嫄金志超
Owner NINGXIA MEDICAL UNIV