Halogenated diarylurea compounds and application thereof in preparation of antiallergic drugs

A technology of halogenated diaryl urea and diaryl urea, which is applied in drug combination, allergic diseases, organic chemistry, etc., can solve the problems of unreported anti-allergic research, and achieve the enrichment of anti-allergic drug types, The effect of suppressing anaphylaxis

Inactive Publication Date: 2020-12-15
XI AN JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Diaryl urea compounds are widely used as herbicides and plant growth regulators in agriculture; they are often used as important inter...

Method used

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  • Halogenated diarylurea compounds and application thereof in preparation of antiallergic drugs
  • Halogenated diarylurea compounds and application thereof in preparation of antiallergic drugs
  • Halogenated diarylurea compounds and application thereof in preparation of antiallergic drugs

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Experimental program
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Embodiment 1

[0044] A class of halogenated halogenated diaryl urea compounds disclosed in the present invention is compound 10-20. The compound structural formula is shown in Table 1 above, and the structural analysis NMR data of compound 10-compound 20 are as follows:

[0045] Compound 10: Dissolve bis(trichloromethyl)carbonate (BTC) (0.25g, 0.83mmol) in 20mL of anhydrous dichloromethane under ice bath conditions and stir for 5min, slowly add 3-bromo-5- The dichloromethane solution of trifluoromethylaniline (0.5g, 2.08mmol) was stirred for 15min after the dropwise addition was completed, and the dichloromethane solution of triethylamine (0.25g, 2.50mmol) was continuously dropped into the cloudy solution. Stir for 15min, then add dropwise a dichloromethane solution of 3-bromo-5-trifluoromethylaniline (0.5g, 2.08mmol) and triethylamine (0.25g, 2.50mmol) to the reaction solution, and stir after the addition is complete 20min, the reaction solution was successively washed with saturated NaHCO...

Embodiment 2

[0057] 1. Experimental materials

[0058] Instrument: Automatic microplate reader was purchased from Bio-Rad (California, USA).

[0059] Cell line: KU812 was cultured in IMEM medium with 10% serum, plus 1:100 penicillin-streptomycin. The medium was half-replaced with fresh medium every other day to maintain the cells at 2 × 10 6 density of cells per milliliter.

[0060] Main reagents: TM buffer solution (composition (g / L): 6.954g NaCl, 0.353g KCl, 2.383g HEPES, 0.162g KH 2 PO 4 ,0.282g CaCl 2 , 0.143 MgSO 4 , 0.991g glucose, 1g bovine serum albumin. 0.1% Triton X-100 lysate; 1mmol / L β-hexosamine solution; 0.1mol / L Na 2 CO 3 / NaHCO 3 Stop solution (pH11.0).

[0061] 2. Experimental method

[0062] KU812 cells were seeded in 96-well plates at 30,000 cells / well and cultured overnight. After the 96-well plate was centrifuged at 1500rpm for 5 minutes, the original medium was discarded, and different drugs were added according to the preset groupings: 90 μL TM buffer was a...

Embodiment 3

[0070] 1. Experimental materials

[0071] Instrument: LCMS-8040 triple quadrupole liquid chromatography mass spectrometry (Shimadzu, Japan)

[0072] Cell line: KU812 was cultured in IMEM medium with 10% serum, plus 1:100 penicillin-streptomycin. The medium was half-replaced with fresh medium every other day to maintain the cells at 2 × 10 6 density of cells per milliliter.

[0073] Basic chromatographic conditions: chromatographic column: Venusil HILIC column (3μm, 2.1×150mm); mobile phase is acetonitrile (0.1% formic acid): 20mM ammonium formate water = 80:20; flow rate: 0.3mL / min; column temperature: 35°C.

[0074] 2. Experimental method

[0075] KU812 cells were seeded in 96-well plates at 30,000 cells / well and cultured overnight. The 96-well plate was centrifuged at 1500 rpm for 5 minutes, and the culture medium was discarded by suction. Add 50 μL of prepared drugs with a series of concentrations to the administration group; add 50 μL TM buffer to the blank group and ...

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Abstract

The invention discloses halogenated diarylurea compounds and application thereof in preparation of an antiallergic drug, and discloses for the first time that the halogenated diarylurea compounds caneffectively antagonize beta-aminohexylglycosidase release and histamine release of human basophilic granulocyte KU812 caused by C48/80, so as to inhibit anaphylactoid reaction. Therefore, when the halogenated diarylurea compounds are used as an anti-allergic preparation, the types of anti-allergic medicines are enriched, and more possible treatment schemes are provided for clinical anti-allergic treatment.

Description

technical field [0001] The invention belongs to the technical field of biomedicine, and in particular relates to a class of halogenated diaryl urea compounds and their application in the preparation of antiallergic drugs. Background technique [0002] Anaphylaxis refers to the process in which antigens or other small molecules directly activate mast cells and stimulate the body to produce allergic-like symptoms without the mediation of IgE and other immunoglobulins. When an allergen comes into contact with the body for the first time, allergic symptoms will appear. Because its clinical manifestations are similar to type I allergic reactions, it is called anaphylactoid reaction. Clinically, anaphylactoid reactions are often caused by drugs. When drugs stimulate human basophils, they can cause an increase in the intracellular calcium ion concentration and trigger a degranulation reaction. [0003] β-hexosaminidase release amount and histamine release amount detection experime...

Claims

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Application Information

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IPC IPC(8): A61K31/17A61P37/08C07C275/30
CPCA61K31/17A61P37/08C07C275/30
Inventor 贺怀贞王程王楠贺浪冲胡甜侯亚静
Owner XI AN JIAOTONG UNIV
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