Application of trialdehyde phloroglucinol thiosemicarbazone hybrid compound in antineoplastic drugs

A technology for reducing amino groups of trialdehyde group phloroglucinol and amino reduction technology of aldehyde group phloroglucinol, which is applied in the field of trialdehyde group phloroglucinol thiosemicarbazones, and can solve the problem of amino reduction without trialdehyde group phloroglucinol Reported issues such as thiourea, to achieve the effects of poor curative effect, short survival period, and rapid disease progression

Active Publication Date: 2020-05-15
INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The present invention relates to the application of trialdehyde group phloroglucinol thiosemicarbazone (I) in the pharmaceutical field, there is no trialdehyde group phloroglucinol thiosemicarbazone (I) provided by the present invention and its function as There is no report on the drug of the active ingredient, and there is no report on the application of the compound or its pharmaceutical composition in the preparation or treatment of diseases such as tumors caused by various factors

Method used

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  • Application of trialdehyde phloroglucinol thiosemicarbazone hybrid compound in antineoplastic drugs
  • Application of trialdehyde phloroglucinol thiosemicarbazone hybrid compound in antineoplastic drugs
  • Application of trialdehyde phloroglucinol thiosemicarbazone hybrid compound in antineoplastic drugs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Synthesis and structure identification of embodiment 1 compound

[0026] The preparation steps of 2,2',2"-((2,4,6-trihydroxyphenyl-1,3,5-triyl)tri(methylidene))tri(thiosemicarbazide) of the present invention are as follows: Weigh 10mmol2,4,6-triformylpyroglucinol and 33mmol thiosemicarbazide (6.485g) into a reaction flask, then add 50mL of ethanol (95%) and stir evenly, then add 3mL of glacial acetic acid dropwise, and then 65- Reflux and stir at 70°C for about 10 hours, evaporate most of the ethanol under reduced pressure, add 20 ml of ice water, filter to obtain a precipitate, wash the precipitate with ice water (30 mL for three times), and recrystallize from ethanol to obtain compound I. 1 H NMR (DMSO-d 6 ,500MHz,ppm):δ11.50(broad,NH),11.10(s,NH),8.56(s,3H),8.06(broad,OH); 13 C NMR (DMSO-d 6 ,125MHz,ppm):δ177.4(3C),160.0(3C),142.3(3C),99.6(3C)

Embodiment 2

[0027] Example 2 2,2',2"-((2,4,6-trihydroxyphenyl-1,3,5-triyl)tri(methylidene))tri(thiosemicarbazide)(I) Study on the proliferative activity of HepG2 cells

[0028] 1. Experimental drugs

[0029] 2,2',2"-((2,4,6-trihydroxyphenyl-1,3,5-triyl)tri(methylidene))tri(thiosemicarbazide)(I) was synthesized by our laboratory It is prepared by using DMSO to aid dissolution, and configured as a 20mg / ml storage solution for long-term storage. The maximum concentration for the experiment is 5, 10, and 20 μg / ml.

[0030] 2. Cell lines

[0031] Human hepatoma cells (HepG2) were purchased from the Shanghai Cell Bank of the Chinese Academy of Sciences. Use DMEM medium containing 10% peptide bovine serum at 37°C with a volume fraction of 5% CO 2 1. Routine culture in the air under fully saturated humidity conditions, replace the medium after 48 hours, when the cell growth reaches saturation, digest with 0.25% trypsin and passage once every 2-3 days, and use logarithmic growth phase cells in...

Embodiment 3

[0036] Example 3 2,2',2"-((2,4,6-trihydroxyphenyl-1,3,5-triyl)tri(methylidene))tri(thiosemicarbazide)(I) Study on the clone formation of HepG2

[0037] 1. Experimental cells:

[0038] Same as Example 1

[0039] 2. Experimental drugs:

[0040] Same as Example 1

[0041] 3. Experimental method:

[0042] Take the logarithmic phase liver cancer HepG2 cells, trypsinize and resuspend, inoculate in a six-well plate, inoculate 200 cells per well, and store at 37°C, 5% CO 2 After culturing in the incubator for 24 hours, different concentrations of compound (I) (5, 10, 20 μg / mL) were added for 10 days, and the medium was replaced every 2 days, and a blank group (DMSO) was set at the same time. After the experiment, discard the medium, fix the cells with 4% paraformaldehyde for 15 min, wash the cells with PBS 3 times, add 1 mL of crystal violet with a mass fraction of 0.2% to each well, act for 15 min, wash the cells with PBS 3 times After the culture plate is dried, take pictures ...

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PUM

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Abstract

The invention relates to an application of 2,2',2''-((2,4,6-trihydroxybenzene-1,3,5-triyl)tris(methanylylidene))tris(hydrazinecarbothioamide) in the preparation of antitumor drugs, especially in the preparation of anti-liver cancer drugs. Cell proliferation, cell morphology, cell colony formation, apoptosis, cell cycle, molecular biology and other experiments prove that the compound can effectively inhibit the proliferation of tumor cells, inhibit the tumor cell cloning formation, induce tumor cell apoptosis and affect the cycle of the tumor cells, has significant influences on proteins associated with tumor apoptosis, and has significant antitumor activity. The application provides a basis for the development of novel antitumor drugs, and the compound has a good clinical application prospect. The 2,2',2''-((2,4,6-trihydroxybenzene-1,3,5-triyl)tris(methanylylidene))tris(hydrazinecarbothioamide) which can be used as a pharmaceutically active ingredient and a pharmaceutically acceptablecarrier can be used to prepare an antitumor medicinal composition.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to the pharmacological activity and pharmaceutical use of trialdehyde phloroglucinol thiosemicarbazone (I). The compound can be used for preventing and / or treating diseases such as tumors or cancers caused by various factors. Background technique [0002] Liver cancer is one of the common malignant tumors in my country. Liver cancer includes primary liver cancer and metastatic liver cancer. People usually refer to primary liver cancer when they say liver cancer. Primary liver cancer is one of the most common clinical malignant tumors, and its mortality rate is second only to gastric cancer and esophageal cancer. According to the latest statistics, about 600,000 new liver cancer patients are diagnosed every year in the world, ranking fifth among malignant tumors. my country is a big country with hepatitis B. Most of the liver cancer in our country develops on the basi...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K31/175A61P35/00
CPCA61K31/175A61P35/00
Inventor 史大永郭传龙王立军江波李祥乾
Owner INST OF OCEANOLOGY - CHINESE ACAD OF SCI
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