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N-substituted thiazolidone compound and application thereof

A technology of thiazolidinone and compound, applied in the field of medicinal chemistry, to achieve the effect of great development and application prospects

Pending Publication Date: 2022-02-18
HANGZHOU INST FOR ADVANCED STUDY UCAS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Searched by authoritative organizations, 2-phenylimino-N-(3-methoxypropyl)-5-(2,4,5-trimethoxybenzylidene)thiazolidinone and its aromatic hydrocarbon The application of receptor antagonists has not been reported in the literature

Method used

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  • N-substituted thiazolidone compound and application thereof
  • N-substituted thiazolidone compound and application thereof
  • N-substituted thiazolidone compound and application thereof

Examples

Experimental program
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preparation example Construction

[0026] The preparation method of the compound of the above formula (I) is to use phenyl isothiocyanate as the starting material, react with methoxypropylamine to generate substituted phenylthiourea, and then undergo a ring-closing reaction with ethyl chloroacetate to form The N-substituted thiazole heterocyclic ring is finally condensed with substituted benzaldehyde to obtain the final product, and the specific steps are shown in Example 1.

[0027] The N-substituted thiazolidinone compound of the present invention can be used as an aromatic hydrocarbon receptor antagonist, wherein the compound is 2-phenylimino-N-(3-methoxypropyl)-5-(2,4 ,5-trimethoxybenzylidene)thiazolidinone.

[0028] In order to better understand the essence of the present invention and the effects of the compounds described in the invention, the following combined with the experiments and results of the MPTO compound further elaborates its application as an aromatic hydrocarbon receptor antagonist in block...

Embodiment 1

[0037] The preparation of 2-phenylimino-N-(3-methoxypropyl)-5-(2,4,5-trimethoxybenzylidene)thiazolidinone, the synthetic route is shown in (Ⅱ):

[0038]

[0039] [1] Dissolve 6.75g (50mmol) of phenyl isothiocyanate in 25mL of methanol solution, add 5.34g (60mmol) of 3-methoxypropylamine, and heat to 80°C under reflux with stirring, the mixture becomes clear, and the reaction 12 After one hour, thin-layer chromatography (TLC) monitors reaction, and after reaction finishes, mixture is cooled to room temperature, and viscous oily liquid appears, extracts with ethyl acetate, and extracting solution is with 10% hydrochloric acid solution, sodium chloride saturated solution, The deionized water was washed successively, and the solvent was distilled off from the extract under reduced pressure to obtain N-(3-methoxypropyl)phenylthiourea.

[0040] [2] Dissolve 1.34g (6.0mmol) of N-(3-methoxypropyl)phenylthiourea and 2.48g (30mmol) of anhydrous sodium acetate in 20mL of ethanol, and ...

Embodiment 2

[0045] 2-phenylimino-N-(3-methoxypropyl)-5-(2,4,5-trimethoxybenzylidene)thiazolidinone compound inhibits CYP1A1 gene expression caused by TCDD (1nmol) raised.

[0046] 1. Dilute HepaWT cells at 1×10 4 / mL density to inoculate cell culture dishes with a diameter of 60 mm. After 24h, first add 2-phenylimino-N-(3-methoxypropyl)-5-(2,4,5-trimethoxybenzylidene)thiazolidinone (10μmol), CH223191 (10μmol , classic AhR small molecule inhibitor) were added to two petri dishes respectively, 1nmol of TCDD was added after 1 hour, DMSO was added to the other two petri dishes as a negative control and TCDD (1nmol) was used as a positive control. %CO 2 Under the conditions of the role of 24h.

[0047] 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 centrifu...

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Abstract

The invention discloses an N-substituted thiazolidinone compound, and particularly relates to 2-phenylimino-N-(3-methoxy propyl)-5-(2, 4, 5-trimethoxy benzylidene) thiazolidinone and application of the 2-phenylimino-N-(3-methoxy propyl)-5-(2, 4, 5-trimethoxy benzylidene) thiazolidinone as a blocking agent of an aromatic hydrocarbon receptor signal channel. According to the invention, experiments prove that the compound can effectively inhibit the up-regulation of gene and protein expression of a metabolic enzyme CYP1A1 of an exogenous material related to a downstream target gene of an aromatic hydrocarbon receptor in mouse liver cancer cells caused by TCDD at the concentration of 10 [mu]M, so that it is prompted that the compound takes an aromatic hydrocarbon receptor as a target, can effectively block the activation of an aromatic hydrocarbon receptor signal channel, reduces the damage of multi-aromatic ring pollutants to an organism through the aromatic hydrocarbon receptor signal channel, and has wide clinical application prospects and economic development values.

Description

technical field [0001] The invention belongs to the field of medicinal chemistry, and relates to an N-substituted thiazolidinone compound and its application, in particular to 2-phenylimino-N-(3-methoxypropyl)-5-(2,4,5- Trimethoxybenzylidene)thiazolidinones and their use as aryl hydrocarbon receptor antagonists. Background technique [0002] Dioxin-like compounds are persistent organic pollutants ubiquitous in the environment, with the characteristics of semi-volatility, bioaccumulation, persistence and toxicity. It is mainly produced in the process of industrial production and waste incineration. Due to its stable chemical structure and high fat solubility, it is widely distributed in natural environments such as air, soil and water. Food chain enrichment is the main way for this kind of compound to exist in the human body, which seriously endangers human health and has attracted worldwide attention. The research on its toxic effect and mechanism of toxicity is the focus o...

Claims

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Application Information

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IPC IPC(8): C07D277/54A61P39/02A61P43/00
CPCC07D277/54A61P39/02A61P43/00
Inventor 刘寅唐利娟赵斌谢群慧徐丽闫兵
Owner HANGZHOU INST FOR ADVANCED STUDY UCAS
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