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Compound dimethoxystyryl-amino-benzimidazolyl-triazine and salt thereof as well as preparation method and application

A technology based on dimethoxystyrene and benzimidazole, which is applied in the field of biopharmaceuticals to achieve the effects of low equipment requirements, large-scale production, and simple processes

Active Publication Date: 2018-06-12
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] After research, the compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzimidazolyl-[1,3,5]triazine has the The therapeutic effect is very good, and so far, there is no information about the compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzo Pharmacodynamic study of imidazolyl-[1,3,5]triazines in tumor

Method used

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  • Compound dimethoxystyryl-amino-benzimidazolyl-triazine and salt thereof as well as preparation method and application
  • Compound dimethoxystyryl-amino-benzimidazolyl-triazine and salt thereof as well as preparation method and application
  • Compound dimethoxystyryl-amino-benzimidazolyl-triazine and salt thereof as well as preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzoimidazolyl-[1,3,5]triazine (referred to as G03) preparation of

[0045] The chemical synthesis route is as follows:

[0046]

[0047] Preparation of 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzimidazolyl-[1,3,5]triazine, specific synthesis steps as follows:

[0048] (1) Synthesis of 2-methyl-1,3-benzoxazol-4-one perchlorate

[0049] Add 6.85g of salicylamide and 30mL of acetic anhydride in a 100mL four-neck flask, stir for 10min, then add 5mL of perchloric acid (70wt%), react at room temperature, and precipitate a solid quickly, add diethyl ether to mix and filter, and wash the solid with diethyl ether. Dry to obtain off-white product 12.0g, yield 92%, 205 ℃ of melting points (Ryabukhin, Yu.I., Mezheritskii, V.V., Karpenko, V.D., and Dorofeenko, G.N., Khim.Geterotsikl.Soedin., 1975, p.1184. );

[0050] (2) Synthesis of (E)-2-(3',4'-dimethoxystyryl)-1,3-benzoxazol-4-one perchlorate

[0051] Add 2-meth...

Embodiment 2

[0056] MTT (3 -(4,5-dimethylthiazole-2)-2,5-diphenyltetrazolium bromide) experiment

[0057] (1) Plating: Hela, MCF-7, MDA-MB-231, HCT116 and HepG2 cell lines in logarithmic growth phase were taken, and 3500 cells / well were spread in 96-well plates, 100 μl per well;

[0058] (2) Dosing: After 24 hours of adherence, the original culture medium was carefully sucked away, and the medicine was added, 100 μl per well; a medicine-dosing group, a control group, and a blank group were set;

[0059] Dilute the compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzimidazolyl-[1,3,5]triazine with medium Dosing at 100uM, 50uM, 25uM, 12.5uM, 6.25uM, 3.125uM, 1.5625uM and 0.78125uM, with the highest concentration not exceeding 100uM; the control group was added with blank medium; the blank group was the control group without cells;

[0060] (3) Incubation: at 5vol% CO 2 , Incubate at 37°C for 48h;

[0061] (4) Add MTT: add MTT (2.5 mg / ml) at 20 μl per well, and place in an incubator ...

Embodiment 3

[0069] Immunofluorescence experiment

[0070] (1) Plating: take the Hela cell line cells in the logarithmic growth phase, and plate at a density of 50vol% at the bottom of each well in a 24-well plate;

[0071] (2) Dosing: After the cells adhere to the wall overnight, dosing according to the concentration gradient of 2.5uM, 5uM and 10uM, the solvent control group was given blank medium, and the positive control group was given 10uM paclitaxel;

[0072] (3) Incubation: at 5vol% CO 2 , Incubate at 37°C for 4h, 8h, and 24h time points.

[0073] (4) After the incubation is completed, the culture medium is discarded, and washed twice with PBS, each time for 5 minutes;

[0074] (5) Fixation and permeabilization: 400 μl ice methanol per well, permeabilization for 5 minutes;

[0075] (6) Blocking: 2.5 wt% BSA was prepared in PBS, centrifuged at 13000 rpm for 10 min before use, and 300 μl BSA per well was blocked at room temperature for 25 min;

[0076] (7) Incubate the primary ant...

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Abstract

The invention discloses a compound dimethoxystyryl-amino-benzimidazolyl-triazine and salt thereof as well as a preparation method and application. The compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1, 2]-benzimidazolyl-[1, 3, 5]-triazine has a good anti-tumor activity against a plurality of tumor cell lines, and obviously influencesan obvious influence on the tumor cell microtubules, wherein theeffect on the cell microtubules is in positive correlation with the time and the concentration, and the compound has a broad application prospect in the anti-tumor field; meanwhile, the preparation method of the compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1, 2]-benzimidazolyl-[1, 3, 5]-triazine has the advantages of simple technology and low equipment requirements and promotes large-scale production.

Description

technical field [0001] The invention belongs to the field of biopharmaceuticals, in particular to the compound 2-[(E)-3',4'-dimethoxystyryl]-4-amino-[1.2]-benzimidazolyl-[1,3, 5] Triazine and its salt, preparation method and application. Background technique [0002] Cancer is one of the major diseases that endanger human health and life. According to the World Cancer Report 2014 issued by the International Cancer Center (IARC) under the World Health Organization, 14 million people were diagnosed with cancer in 2012. It is estimated that by 2025, the number of new cancer cases worldwide will increase to 19 million per year, to 22 million by 2023, and to 24 million by 2035, that is, cancer cases will increase by 50% in the next 20 years. According to the report data, the number of new cancer cases and deaths in my country ranks first in the world. [0003] On October 9, 2015, Chen Wanqing, director of the National Cancer Prevention and Research Office and the National Canc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A61P35/00
CPCC07D487/04
Inventor 王领曾然然罗瑶
Owner SOUTH CHINA UNIV OF TECH
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