Diarylethene structure similar compounds as well as preparation method and application thereof

A compound and vinyl technology, applied in the field of chemical total synthesis of natural product kalinin analogues, can solve the problems of in-depth research on the pharmacological effects of natural product kalinin, the limited number of analogues, etc.

Active Publication Date: 2014-08-20
MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] However, at present, domestic and foreign chemical research on pigeonil stilbene substances is still limited to the level of natural medicinal chemistry such as extraction, separation and structure identification of natural products, and the number of analogues with definite structures obtained is very limited
Moreover, limited by the source of the drug, it is difficult to carry out in-depth research on the pharmacological effects of the natural product lignanin.

Method used

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  • Diarylethene structure similar compounds as well as preparation method and application thereof
  • Diarylethene structure similar compounds as well as preparation method and application thereof
  • Diarylethene structure similar compounds as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0102] Preparation of methyl 2,4-dihydroxy-6-methylbenzoate (2)

[0103] Methyl acetoacetate (50g, 0.43mol) was dissolved in 300ml of ether, NaH (15.50g0.45mol, 70%) was added at room temperature, after the addition, the ether solution of diketene (37g, 0.45mol) was added dropwise at this temperature After the addition, react at room temperature for 3-4 hours, at which time the reaction system becomes yellow turbid liquid. The reaction was terminated, the reaction solution was added to 500 ml of ice-water mixture, the ether layer was separated, the water layer was extracted twice with 50 ml of ether, the ether layers were combined, washed with saturated brine, and dried overnight with anhydrous magnesium sulfate. Filtration, rotary evaporation to remove the ether, the residue was passed through a silica gel column with petroleum ether: ethyl acetate = 8:1 to obtain 35 g (45%) of white solid as the target product. 1 H-NMR(400M,DMSO-d 6 )δ(ppm): 10.66(s,1H),9.95(s,1H), 6.16(d,J=2.4...

Embodiment 2

[0105] Preparation of 2,4-Dimethoxy-6-methylbenzoic acid methyl ester (3)

[0106] Compound 2 (12g, 0.066mol) was dissolved in 50ml of acetone, potassium carbonate (27.3g, 0.198mol), methyl iodide (28g, 0.198mol) were added, and the reaction was heated to reflux for 3h. The reaction was stopped. The reaction solution was added to 100ml of water and acetic acid Extract with ethyl acetate (350 ml), combine the organic layers, and wash the organic layers with 10% sodium hydroxide solution, 10% hydrochloric acid, and saturated brine in sequence. The organic layer was dried with anhydrous magnesium sulfate. After filtration, the solvent was removed by rotary evaporation to obtain a colorless oil, which was recrystallized with petroleum ether / ethyl acetate to obtain 13.5 g (97%) of colorless crystals. 1 H-NMR(400M,CDCl 3 )δ(ppm): 6.31(s, 2H), 3.88(s, 3H), 3.80(s, 6H), 2.28(s, 3H)

Embodiment 3

[0108] Methyl 2-bromomethyl-4,6-dimethoxybenzoate (4)

[0109] Compound 3 (10g, 0.0476mol) was dissolved in 50ml of carbon tetrachloride, protected by nitrogen, heated to reflux, and a mixture of NBS (8.5g, 0.0476mol) + BPO (0.11g, 0.476mmol) was added in batches. After the addition, reflux Reaction for 1h. The reaction was stopped, cooled, filtered, and the filtrate was spin-dried to obtain a pale yellow solid, which was recrystallized from absolute ethanol to obtain 11.3 g (82%) of a white solid. 1 H-NMR(400M,CDCl 3 )δ(ppm): 6.74(s, 1H), 6.47(s, 1H), 4.66(s, 2H), 3.96(s, 3H), 3.93(s, 3H), 3.85(s, 3H).

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Abstract

The invention discloses a group of diarylethene structure similar compounds as well as a preparation method and application thereof. The provided compounds have a structure of a general formula I. Moreover, the invention further provides medicinal compositions containing the compounds serving as active ingredients. Researches discover that the compounds have pharmacological activities of resisting influenza viruses, Coxsackie B3 viruses, AIDS viruses, hepatitis B viruses, hepatitis C viruses and the like. Therefore, the invention further provides the application of the compounds and the medicinal compositions containing the compounds serving as active ingredients in preparation of anti-virus medicaments. The invention lays a foundation for deeply researching and developing the application of the compounds as clinical medicaments. The general formula I is as shown in the specification.

Description

Technical field [0001] The invention relates to a group of diarylethylene structurally similar compounds and a preparation method thereof, and also relates to the application of the compounds in anti-influenza virus infection, Coxsackie B3 virus, AIDS virus, hepatitis B virus, hepatitis C virus and other medicines. And pharmaceutical compositions containing such compounds as active components and applications thereof. The present invention also relates to a chemical total synthesis method of natural product xylin analogs. Background technique [0002] Cajanus cajan L. Millsp. is a plant belonging to the genus Cajanus cajan in the leguminous family. It is the sixth largest edible legume in the world and the only woody edible legume. Mainly distributed in Southeast Asia, India, Myanmar and my country's Yunnan, Sichuan, Jiangsu, Guangdong, Guangxi, Taiwan and Hainan. Pigeon pea plants have a wide range of medicinal values. The main effects of its seeds are the treatment of liver a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/30C07D233/64C07D207/337C07D263/32C07D307/54C07D213/64C07D213/69C07D207/36C07D307/58C07D277/34C07D263/38C07D277/24C07D207/333C07D213/80C07D405/06C07D401/06C07D417/06C07D213/803C07C69/94C07C67/30C07C27/02C07C65/28C07C41/18C07C43/23C07C227/16C07C227/18C07C229/60A61K31/625A61K31/618A61K31/603A61K31/426A61K31/4174A61K31/421A61K31/40A61K31/085A61K31/341A61K31/44A61K31/455A61K31/443A61K31/444A61K31/4439A61K31/606A61P31/12A61P31/16A61P31/18A61P31/20A61P31/14
CPCC07C43/23C07C65/28C07C69/94C07C229/60C07D207/333C07D207/337C07D207/36C07D213/64C07D213/69C07D213/80C07D213/803C07D233/64C07D263/32C07D263/38C07D277/24C07D277/30C07D277/34C07D307/54C07D307/58C07D401/06C07D405/06C07D417/06
Inventor 李卓荣郑光辉彭宗根李玉环岑山季兴跃金洁李健蕊孙文芳马玲
Owner MEDICINE & BIOENG INST OF CHINESE ACAD OF MEDICAL SCI
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