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5-(4-Hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone and its application

A kind of methoxybenzylidene, nitroaniline technology, applied in the field of medicinal chemistry, to achieve the effect of great development and application prospects

Active Publication Date: 2019-08-09
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Searched by authoritative organizations, 5-(4-hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino) thiazolidinone and its activity as an aromatic hydrocarbon receptor agonist The application has not been reported in the literature

Method used

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  • 5-(4-Hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone and its application
  • 5-(4-Hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone and its application
  • 5-(4-Hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: Synthesis of 5-(4-hydroxyl-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone

[0023] [1] by HCl:H 2 The ratio of O (1:4) is dubbed hydrochloric acid solution. Weigh 11.4g (150mmol) of ammonium thiocyanate and dissolve it in 50mL of hydrochloric acid solution, add 13.8g (100mmol) of 2-nitroaniline, and heat to 85°C under stirring conditions, the mixture becomes clear, after 12 hours of reaction, TLC monitors the reaction , after the reaction, the mixture was cooled to room temperature, a viscous oily liquid appeared, extracted with ethyl acetate, the extract was washed with 10% hydrochloric acid solution, saturated sodium chloride solution, and water successively, the extract was evaporated under reduced pressure to remove the solvent, 2-Nitrophenylthiourea is obtained.

[0024] [2] Add 1180mg (6.0mmol) of 2-nitrophenylthiourea and 2479mg (30mmol) of anhydrous sodium acetate to 20mL ethanol. Under stirring conditions, add 1.28mL (12mmol) of ethyl c...

Embodiment 2

[0030] Example 2: 5-(4-hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone compound causes CYP1A1 gene expression up-regulation verification

[0031] 1. Dilute HepaWT cells at 1×10 5 mL -1The density was inoculated into cell culture dishes with a diameter of 60 mm. After 24h, the cells were mixed with 5-(4-hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone, DMSO (negative control), TCDD ( positive control) at 37°C with 5% CO 2 Under the conditions of the role of 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 13,000 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 (with absolute ethanol added) to th...

Embodiment 3

[0055] Example 3: 5-(4-Hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone compound causes up-regulation of CYP1A1 protein expression

[0056] 1. Collection of protein in cells

[0057] HepaWT cells were divided into 1×10 5 mL -1 The density was inoculated into cell culture dishes with a diameter of 60 mm. After 24h, the cells were mixed with 5-(4-hydroxy-3-methoxybenzylidene)-2-(2-nitrophenylimino)thiazolidinone, DMSO (negative control), TCDD ( positive control) at 37°C with 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 1000g for 5min at 4°C. Centrifuge, remove the supernatant, and obtain a cell pellet. A...

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Abstract

The invention discloses a compound 5-(4-hydroxyl-3-methoxyl benzylidene)-2-(2-nitryl phenylimino) thiazolidone, HMNT for short, and an application thereof in an aromatic hydrocarbon receptor stimulant, wherein the chemical structure is as shown in a formula (I). Experiments verify that the compound disclosed by the invention effectively causes up-regulation of genetic expression and protein expression of a metabolic enzyme CYP1A1 of a related allogenic material of a downstream target gene of an aromatic hydrocarbon receptor in a mouse hepatoma carcinoma cell at the concentration of 10 mu M and prompts that the compound is the aromatic hydrocarbon receptor stimulant, is expected to become a potential drug by taking the aromatic hydrocarbon receptor as a tumor treating target, and is wide in clinical application prospect.

Description

technical field [0001] The invention relates to a thiazole-containing heterocyclic compound and its application, in particular to 5-(4-hydroxy-3-methoxybenzylidene)-2-(2-nitrobenzimido)thiazolidinone Its application as an aromatic hydrocarbon receptor agonist belongs 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. AhR exists in various tissues and cells 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 and poisons. At the same time, AhR also has many endogenous functions, such as regulating ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/54A61P35/00
CPCC07D277/54
Inventor 闫兵董梦琦赵斌张嵩岩周宏钰刘寅王深清
Owner SHANDONG UNIV
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