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Mutual prodrug and preparation method based on paclitaxel and nitrogen mustard

A paclitaxel and prodrug technology, applied in the field of new synergistic prodrugs and their preparation, to achieve the effects of improved reaction process, novel structure, and reduced toxicity

Inactive Publication Date: 2012-11-07
SHANGHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At the same time, it may also improve the anti-tumor range of this class of drugs

Method used

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  • Mutual prodrug and preparation method based on paclitaxel and nitrogen mustard
  • Mutual prodrug and preparation method based on paclitaxel and nitrogen mustard
  • Mutual prodrug and preparation method based on paclitaxel and nitrogen mustard

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Embodiment 1: The specific synthesis steps of the synergistic prodrug based on paclitaxel-nitrogen mustard of the present invention:

[0028] A. 5-Chloro-2-nitrobenzoic acid (15.02g, 75.4mmol) was dissolved in SOCl 2 (80mL), refluxed for 6 hours; most of the thionyl chloride was evaporated at normal pressure, and the remaining part of the thionyl chloride was removed under reduced pressure to obtain a brown oily 5-chloro-2-nitrobenzoyl chloride crude product, which was added to Diluted with anhydrous tetrahydrofuran; this solution was added dropwise with aniline (7.20g, 78.2mmol) and anhydrous K through a constant pressure funnel at 0°C for 30 minutes 2 CO 3 (10.30g, 75.2mmol) in dry THF (30mL) solution, the reaction mixture continued to stir for 2 hours; after the reaction was over, the solid matter was removed by filtration, and the filtrate was evaporated to remove the solvent under reduced pressure; the crude product was recrystallized in ethyl acetate to obtain A ...

Embodiment 2

[0036] Example 2: Biological activity test of 5-(bis(2-chloroethyl)amino)-2-nitro-N-phenylcarbamoyl-2-aminoethyl-carbonyl paclitaxel

[0037] Specific test process:

[0038] a. Three different tumor cells, LN229, D54MG, and U251MG, were implanted in 96-well plates, 80,000 cells / well, placed at 37°C, 5% CO 2 Cultivate in the incubator for 24 hours;

[0039] b. Add different concentrations of synergistic prodrug (H) and paclitaxel solutions to the cells cultured in step a, and place at 37 ° C, 5% CO 2 Cultivate in the incubator for 2 hours;

[0040] c. Divide the cells in step b into two groups, one of which is set at 37°C, 1%O 2 Cultivate in the incubator for 72 hours, and the other group is placed at 37 ° C, 21% O 2 Cultivate in the incubator for 72 hours;

[0041] d. Add 20 μL of 5 mg / ml MTT solution to each well of the cells cultured in step c, add the solution after 4 hours of action, 100 μL / well, put it in the incubator, and measure it with MK-2 automatic microplate r...

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PUM

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Abstract

The invention relates to a mutual prodrug and a preparation method thereof based on paclitaxel and nitrogen mustard. The structure formula of the mutual prodrug is characterized in that: the toxicity of the mutual prodrug in normal state is greatly reduced, and the mutual prodrug has potential application values.

Description

technical field [0001] The invention relates to a novel synergistic prodrug and a preparation method thereof, in particular to a paclitaxel-nitrogen mustard-based synergistic prodrug and a preparation method thereof. Background technique [0002] In most countries today, the death caused by malignant tumors is the second leading cause of death after cardiovascular and cerebrovascular diseases. In addition to inhibiting and poisoning actively proliferating tumor cells, traditional antineoplastic drugs also inhibit other rapidly proliferating normal cells, resulting in many serious side effects, such as nausea, vomiting, bone marrow suppression and hair loss. [0003] With the improvement of living standards, people's expectations for cancer treatment have increased, hoping that people's health will not be greatly affected while cancer is cured. Therefore, it is particularly important to develop new anti-tumor drugs that can selectively act on tumor cells and have no toxicity...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D305/14A61K31/337A61P35/00
Inventor 林海霞邵军超靳丹辉阮非黄嘉辰
Owner SHANGHAI UNIV