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Sulfatriazole-type tubulin polymerization inhibitor and its synthesis method and application

A technology of triazole and sulfonamide is applied in the field of antitumor medicinal chemistry to achieve the effect of simple and efficient synthesis method

Inactive Publication Date: 2021-06-04
ZHENGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

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  • Sulfatriazole-type tubulin polymerization inhibitor and its synthesis method and application
  • Sulfatriazole-type tubulin polymerization inhibitor and its synthesis method and application
  • Sulfatriazole-type tubulin polymerization inhibitor and its synthesis method and application

Examples

Experimental program
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Effect test

Embodiment 1

[0022] Example 1 Preparation of Compound (I)

[0023] The thiophene sulfonyl chloride (0.96 g, 5 mmol) and anhydrous potassium (1.38 g, 10 mmol) were mixed, and 10 ml of dichloroethane was added, alkyl amine (5 mmol) was added, and the temperature was increased to 60 ° C, and the reaction was continued. The TLC monitors the reaction process. After the reaction is completed, distilled water is added to the system, quench the reaction, then extract 3 times with dichloroethane, then use saturated brine to fetch dichloroethane phase 3 times, 10ml each time, finally The organic phase was dried over anhydrous magnesium sulfate, filtrates magnesium sulfate, and the filtrate was evaporated to remove dichloroethane. The obtained crude product was separated by silica gel column chromatography, petroleum ether / ethyl acetate = 10: 1 elution, obtained compound (I).

Embodiment 2

[0024] Example 2 Preparation of Formula (II)

[0025] Add compound (I) (5 mmol) and 3-methoxyphenylbenzyl glyzoid compound (6 mmol), then add 20 mlthf / h 2 O (10 ml / 10 ml) dissolved, and finally the copper sulfate (1 mmol) and sodium ascorbate (0.5 mmol) were added, and the mixture was stirred at room temperature overnight. The TLC monitors the reaction process. After the reaction is completed, distilled water was added to the system, then extracted 6 times with dichloroethane, and then withdraw the saline, the dichloroethane phase 3 times, 10ml each time, the final organic phase Magnesium sulfate dried, filtrates magnesium sulfate, and the filtrate was distilled off dichloroethane. The resulting crude product was separated by silica gel column chromatography, petroleum ether / ethyl acetate = 7: 1 elution, it was compound (IIA).

[0026] Compound IIB-IIL was prepared by compound IIA synthesis.

[0027] IIA: White solid, Yield: 80.1%, MP: 104-106 ° C. 1 H NMR (400 MHz, DMSO) δ8...

Embodiment 3

[0039] Example 3 Anti-tumor activity determination of the above compound:

[0040] The compounds used were synthesized and purified by the present invention; sample reserve: Weigh 3-5 mg sample placed in a 1.5 ml EP tube, then formulated with DMSO to form a concentration of 128 × 10 3 The solution of μg / ml, 4 ° C is stored, and the medium is diluted according to the desired concentration during the experiment. After taking the long-term cells, after the digestion, the cell density is tested with medium, inoculated into 96-well plates, 150 μl per well, after 24 h, cultured, cultured The group diluted drugs (50 μg / ml, 100 μg / mL), each concentration set 6 complex apertures, and a blank control group and a negative control group were provided. After the drug was 72h, 20 μl MtT was added to each well, and after 4 h, the liquid was subjected to 150 ml of DMSO, the oscillation, the enzyme detector 490 nm was detected, and the calculated inhibition rate, the calculation formula was ...

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Abstract

The invention discloses a class of sulfonamide-1,2,3-triazole-containing compounds, their preparation method and their application in Tubulin polymerization inhibitors, belonging to the field of antitumor pharmaceutical chemistry. The present invention uses classic click chemistry to combine the sulfa-1,2,3-triazole active unit with the sulfa-1,2,3-triazole active unit, thereby synthesizing the sulfa-1,2,3-triazole compounds in a simple, efficient, and environmentally friendly manner. It has the following general structural formula: the in vitro anticancer activity test of this type of compound shows that it has a certain inhibitory effect on a variety of tumor cells PC-3, MCF-7, MGC-803, and has a significant inhibitory effect on the polymerization of Tubuli , which can be used as a candidate or lead compound for further development in the preparation of antitumor drugs.

Description

Technical field [0001] The present invention relates to the field of anti-tumor pharmaceutical chemistry, and more particularly to a new type of sulfamer-1,2,3-triazozole compound, which uses a new type of anti-tumor drug pioneering compound. Background technique [0002] Microtubules are an important component of most eukaryotic biological skeletons. The microtubule does not only play an important role in maintaining cellular morphology, but also plays an important role in the order of internal structure of cells, but also differentiates from intracellular material transportation, cell movement, and cell. Life activities such as development and cell division breeding are closely related. The important physiological effects of tubulin make it an important target in the field of tumor. Through the principle of splicing, a range of new sulfamer-1,2,3-triazole compound is synthesized, which is conducive to the screening of anti-tumor activity, which is of great significance to devel...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D409/12C07D405/12C07D249/04A61P35/00
CPCC07D249/04C07D405/12C07D409/12
Inventor 付冬君李萍杨佳佳张赛扬张雁冰
Owner ZHENGZHOU UNIV
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