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2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl)methylene-thiazolidin-4-one compound and application thereof

A technology of trifluoromethylaniline and naphthylmethylene, which is applied in the field of medicinal chemistry and achieves the effect of great development and application prospects

Active Publication Date: 2017-06-20
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, after searching and searching by authoritative organizations, it was found that: 2-(4-trifluoromethylphenylimino)-5-(2-naphthylmethylene)thiazolidin-4-one compound and its function as an aromatic hydrocarbon acceptor The application of agonists has not been reported at home and abroad

Method used

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  • 2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl)methylene-thiazolidin-4-one compound and application thereof
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  • 2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl)methylene-thiazolidin-4-one compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Preparation of 2-(4-trifluoromethylphenylimino)-5-(2-naphthylmethylene)thiazolidin-4-one

[0023] According to the ratio of HCl:H2O (1:4) dubbed hydrochloric acid solution. Weigh 11.4g (150mmol) of ammonium thiocyanate and dissolve it in 50mL of hydrochloric acid solution, add 12.4mL (100mmol) of 4-trifluoromethylaniline, and heat to 85°C under stirring conditions, the mixture becomes clear. After 12 hours of reaction, TLC Monitor the reaction. After the reaction, the mixture was cooled to room temperature. A viscous oily liquid appeared, extracted with ethyl acetate, and the extract was washed with 10% hydrochloric acid solution, saturated sodium chloride solution, and water in sequence, and the extract was evaporated under reduced pressure. solvent to obtain 4-trifluoromethylphenylthiourea.

[0024] Add 0.906mL (6.0mmol) of 4-trifluoromethylphenylthiourea and 2479mg (30mmol) of anhydrous sodium acetate into 20mL of ethanol. Under stirring conditions, add 1...

Embodiment 2

[0030] Example 2: 2-(4-trifluoromethylphenylimino)-5-(2-naphthylmethylene)thiazolidin-4-one compound causes CYP1A1 gene expression up-regulation verification

[0031] 1. Inoculate HepaWT cells into a cell culture dish with a diameter of 60mm at a density of 1×105mL-1. After 24h, the cells were mixed with 2-(4-trifluoromethylanilino)-5-(2-naphthylmethylene)-1,3-thiazol-4-one (10μM), DMSO (0.1% , negative control), TCDD (1nM, positive control) at 37°C with 5% CO2 for 24h.

[0032]2. Extraction of RNA: Collect the cells, discard the medium, and rinse twice with preheated PBS solution. Add an appropriate amount of lysis buffer to lyse the cells, and pipette slowly several times. The lysate was transferred to a spin column placed in a 2 mL collection tube and centrifuged at 13000 rpm for 1 min. Discard the supernatant, and put the spin column into a new 2mL collection tube.

[0033] Add 700 μL of Wash Buffer 1 (absolute ethanol has been added) to the spin column, and centrifuge...

Embodiment 3

[0056] Example 3: Verification that 2-(4-trifluoromethylphenylimino)-5-(2-naphthylmethylene)thiazolidin-4-one compound causes up-regulation of CYP1A1 protein expression

[0057] 1. Dilute HepaWT cells at 1×10 5 mL -1 The density was inoculated into cell culture dishes with a diameter of 60 mm. After 24 h, the cells were mixed with 2-(4-trifluoromethylanilino)-5-(2-naphthylmethylene)-1,3-thiazolidin-4-one (10 μM), DMSO (5 %, negative control), TCDD (1nM, positive control) at 37°C containing 5% CO 2 Under the conditions of the role of 24h.

[0058] Discard the culture medium in the dish, and wash three times with 4°C pre-cooled PBS. After discarding the PBS, place the dish on ice and add 4 mL of PBS. Cells were scraped off with a cell scraper. The remaining cells were observed under a microscope. Suck the PBS into a sterile 15mL centrifuge tube with a sterile hose, and centrifuge at 1000rpm for 5min at 4°C. Centrifuge, remove the supernatant, and obtain a cell pellet. A...

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Abstract

The invention discloses a thiazole heterocyclic compound. The thiazole heterocyclic compound is 2-(4-trifluoromethyl-phenylimino)-5-(2-naphthyl) methylene-thiazolidin-4-one compound, which is referred as TNTO and has a chemical structure as shown in a general formula (I). The invention further discloses an application of the compound as an aromatic hydrocarbon receptor stimulant. Experiments prove that the thiazole heterocyclic compound under the concentration of 10 muM can remarkably up-regulate the gene, protein expression of the related exogenous substance metabolic enzyme CYP1A1 of the downstream target gene of the aromatic hydrocarbon receptor in the mouse liver cancer cells, the compound is prompted to be an agonist of an aromatic hydrocarbon receptor, and is expected to become a potential medicine which takes the aromatic hydrocarbon receptor as the tumor target, and has wide clinical application prospect and economic development value.

Description

technical field [0001] The invention relates to a thiazole-containing heterocyclic compound and its application, in particular to a 2-(4-trifluoromethylbenimino)-5-(2-naphthylmethylene)thiazolidine-4- A ketone compound and its application as an aromatic hydrocarbon receptor agonist belong to the field of medicinal chemistry. Background technique [0002] The aryl hydrocarbon receptor (AhR) is a member of the basic helix-loop-helix (bHLH) supersubfamily bHLH-PAS (Bhlh-PER-ARNT-SIM). The only receptor that can be activated by ligands. Evolutionary analysis shows that the AhR gene exists in mammals, amphibians, reptiles and birds. It also exists in various tissues and cells such as liver, lung, kidney, placenta, tonsil, and B lymphocytes of the human body. As a ligand-activated transcription factor, AhR mainly regulates the expression of cytochrome P-450 enzyme family phase I (CYP1) and some phase II metabolic enzymes, and participates in the metabolic process of some drugs ...

Claims

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Application Information

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IPC IPC(8): C07D277/54A61P35/00
CPCC07D277/54
Inventor 闫兵苗潇元赵斌张嵩岩周宏钰王深清刘寅
Owner SHANDONG UNIV
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