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Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS

A polyhydroxy stilbene and compound technology, which is applied in the preparation of polyhydroxy stilbene compounds and the use of SARS virus-inhibiting drugs, can solve the problems of not detecting that SARS-CoV has an effect and the like

Inactive Publication Date: 2006-02-22
DALIAN UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, SANP did not detect an effect on SARS-CoV

Method used

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  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS
  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS
  • Polyhydroxy stilbenes compound preparation and uses as drugs for suppressing SARS

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0109] (E)-2-[2-(3,5-dihydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine; (also known as: (E)-4,6-dimethyl base-3',5,5'-trihydroxystilbene-2-nitrogen)

[0110] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), 2.5g (0.016mol) of triethyl phosphite, a small amount of tetrabutylammonium iodide, stir, heat in an oil bath to 100-110°C, and react for 3-6h. The reactant was distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red sticky matter in the bottle was directly used for the next reaction.

[0111] Synthesis of (E)-2-[2-(3,5-dimethoxyphenyl) vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate solution obtained in the previous step reaction In 50 mL of dry tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, quickly add NaH powder (0.025 mol) under stirring, and stir for 30 min. With stirring, ...

Embodiment 2

[0114] (E)-2-[2-(4-hydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine (also known as: (E)-4,6-dimethyl-4, 5'-dihydroxystilbene-2-nitrogen)

[0115] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), triethyl phosphite 2.5g (0.016mol), a small amount of tetrabutylammonium iodide, stirred, heated in an oil bath to 100-110°C, and reacted for 3-6h. The reactant was distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red sticky matter in the bottle was directly used for the next reaction.

[0116] Synthesis of (E)-2-[2-(4-methoxyphenyl)vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate obtained in the previous step reaction was dissolved in 50 mL and dried In tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, add NaH powder (0.025mol) rapidly under stirring, and stir for 30min. With stirring, 30 mL...

Embodiment 3

[0119] (E)-2-[2-(2,5-dihydroxyphenyl)vinyl]-3,5-dimethyl-4-hydroxypyridine (also known as: (E)-4,6-dimethyl -2,5,5'-trihydroxystilbene-2-nitrogen)

[0120] Synthesis of 3,5-dimethyl-4-methoxypyridine-2-methylphosphonate: 2-chloromethyl-3,5-dimethyl-4-methoxypyridine was added to a 50mL three-neck flask (0.01mol), triethyl phosphite 2.5g (0.016mol), a small amount of tetrabutylammonium iodide, stirred, heated to 100-110°C in an oil bath, and reacted for 3-6h. The reactants were distilled under reduced pressure below 90°C to remove excess triethyl phosphite, and the remaining light orange-red viscous in the bottle was directly used for the next reaction.

[0121]Synthesis of (E)-2-[2-(2,5-dimethoxyphenyl) vinyl]-3,5-dimethyl-4-methoxypyridine: the phosphonate solution obtained in the previous step reaction In 50 mL of dry tetrahydrofuran (THF), cool in an ice-salt bath to below 0°C, quickly add NaH powder (0.025 mol) under stirring, and stir for 30 min. With stirring, 30 mL o...

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PUM

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Abstract

The invention provides a group of polyhydroxy stilbene compounds, their preparing process and use for suppressing and eradicating SARS coronavirus. The preparing process comprises, preparing phosphonic ester by reacting multi-alkyl substituted chloro (bromo) methoxyl or pyridine compounds with triethyl phosphate, then reacting phosphonate ester compound with multi-alkyl (oxy) phenylpyridine methyl aldehyde to obtain multi-alkyl (oxy) stilbene compounds. Finally acting with boron tribromide to obtain polyhydroxy stilbene compounds with substituent groups.

Description

technical field [0001] The invention relates to a new class of medicinal polyhydroxystilbene compounds, a preparation method and application thereof. This new compound is used for inhibiting and killing SARS coronavirus. Background technique [0002] Stilbene compounds are a general term for a class of compounds with a stilbene core. In nature, polyhydroxystilbene compounds exist in many Chinese herbal medicines such as veratrum, rhubarb, tiger stick, and Shouwu, and are neutralized in foods such as grapes, peanuts, and mulberries. , Improving immunity and many other physiological activities. [0003] In WO 02 / 057219 patent, a class of stilbene compounds are disclosed as regulators of T cells, neutrophils, macrophages and corresponding cytokines for the treatment of immune, inflammatory and autoimmune diseases. In the structure disclosed in the WO02 / 057219 patent, only one benzene ring contains alkoxy or hydroxyl substituents at the 3 and 5 positions, the other benzene ri...

Claims

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Application Information

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IPC IPC(8): C07D213/06C07D213/28C07D213/62C07C39/21C07C37/00C07C43/253A61K31/44A61K31/075A61K31/05A61K9/20A61K9/00A61P31/14A61P11/00
Inventor 赵伟杰李泽琳孟庆伟温瑞兴王世盛曾毅李悦青
Owner DALIAN UNIV OF TECH
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