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Oligopolyphenylene vinyl compound as well as preparation method and application thereof

A polyphenylene vinylene and compound technology, which is applied in the field of oligopolyphenylene vinylene compounds and their preparation, can solve problems such as side effects of medication, killing of tumor cells, and affecting the survival period of patients.

Active Publication Date: 2017-11-24
INST OF CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, there are currently no very effective drugs against drug-resistant tumors
[0004] In addition, most of the existing antineoplastic drugs are cytotoxic drugs, which not only kill tumor cells, but also have relatively large cytotoxic effects on normal cells in the human body, which will lead to serious drug side effects , and even affect the survival period of patients

Method used

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  • Oligopolyphenylene vinyl compound as well as preparation method and application thereof
  • Oligopolyphenylene vinyl compound as well as preparation method and application thereof
  • Oligopolyphenylene vinyl compound as well as preparation method and application thereof

Examples

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preparation example Construction

[0093] In the present invention, the paclitaxel modified with acryloyl chloride is preferably paclitaxel whose 2'-hydroxyl group is modified with acryloyl chloride. The acryloyl chloride-modified paclitaxel can be prepared by conventional chemical methods. In a preferred case, the preparation method of the modified paclitaxel comprises: contacting paclitaxel with acryloyl chloride in an inert atmosphere. Wherein, the dosage ratio of the paclitaxel to the acryloyl chloride is 1:1-2, preferably 1:1-1.5. The contact solvent is dichloromethane. The contacting conditions are as follows: the temperature is -20-60°C, preferably -10-10°C; the time is 1-24 hours, preferably 2-4 hours. The contacting also includes: washing, extracting, drying, solvent evaporation and separation of the product in sequence. Wherein, the washing includes the process of washing with saturated aqueous sodium bicarbonate solution and deionized water; the extraction is carried out with dichloromethane; the ...

Embodiment 1

[0113] This example is used to illustrate the preparation method of compounds with the structures shown in formulas (1)-(5).

[0114] (1) compound shown in preparation formula (8) and formula (9)

[0115] 2.31g of the compound shown in formula (6), 3.67g of 1,2-dibromoethane, 1.38g of potassium carbonate and 2.64g of 18-crown ether-6 were dissolved in 60mL of acetone, and a catalytic amount of potassium iodide was added, stirred in an ice bath Oxygen was removed under nitrogen protection and reacted at 75°C for 24 hours. After the mixture was cooled to room temperature (25°C), it was washed once with 1 mL of saturated aqueous sodium bicarbonate solution and twice with 2 mL of deionized water, and 10 mL of dichloromethane was added to extract the product. The organic phase was dried with anhydrous magnesium sulfate, evaporated to After the solvent was separated by silica gel column (eluent: petroleum ether: ethyl acetate: dichloromethane = 10:2:1 (volume ratio)), 1.81 g of whi...

Embodiment 2

[0143] This example is used to illustrate the application of the OPV-SH compound of the present invention in the preparation of preparations for cell imaging.

[0144] Cell imaging experiments were performed using the OPV-SH obtained in Example 1, and characterized by a Confocal laser scanning microscope (FV1000-IX81, Olympus, Japan).

[0145] The specific steps are: Human lung cancer cell A549 is cultivated in a glass-bottomed culture dish with DMEM cell culture medium containing 10% serum for 24 hours. When the number of cells reaches nearly 60, add 2.5 micromoles of OPV-SH compound and continue to cultivate for 4 hours. , and set the control dish at the same time. The culture solution was removed and 100 nanomole of lysosome fluorescent dye (Lysotracker DND-99, Invitrogen) preheated at 37°C was added, and stained for 20 minutes. After staining, remove the culture medium carefully, wash with PBS three times, add PBS solution with a mass concentration of 4% paraformaldehyde,...

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Abstract

The invention relates to the field of antitumor drugs and discloses an oligopolyphenylene vinyl compound as well as a preparation method and application thereof. The oligopolyphenylene vinyl compound provided by the invention is of a structure shown in a formula (3), wherein n is an integer of 2-10. The provided compound of the structure shown in the formula (3) has good tumor cell proliferation inhibiting effect, especially has good inhibitory effect on proliferation of drug-resistant tumor cells, but has smaller toxic and side effects on normal cells. (The formula (3) is described in the specification.).

Description

technical field [0001] The present invention relates to the field of antitumor drugs, in particular to an oligomerized phenylene vinylene compound and its preparation method and application. Background technique [0002] The morbidity and mortality of cancer in my country are on the rise rapidly. Tumors cause great pain to patients and their families, and take up a lot of social resources and wealth. Tumors have become an increasingly serious public health problem facing mankind. [0003] In the field of tumor treatment, chemotherapy resistance often occurs during the treatment of cancer patients. Most drugs are found to be resistant after a period of use, resulting in poor efficacy of conventional chemotherapy for many tumors and poor prognosis, which has become a clinical problem. important problem. Initially, patients may experience tumor shrinkage or stable disease for a period of time after chemotherapy treatment. However, drug resistance occurs to varying degrees af...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/16C07C323/52C07D305/14C07D519/04C09K11/06A61K41/00A61K31/337A61K31/138A61K31/475A61K47/58A61P35/00G01N21/64
CPCY02P20/55C07C271/16A61K31/138A61K31/337A61K31/475A61K41/0057C07C323/52C07D305/14C07D519/04C09K11/06C09K2211/1007G01N21/6486A61K2300/00
Inventor 王树周凌云刘礼兵吕凤婷
Owner INST OF CHEM CHINESE ACAD OF SCI
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