2,3-diarylindene derivatives, and preparation method, pharmaceutical compositions and application thereof

A technology of derivatives and aryl indene, applied in the direction of drug combination, preparation of carbon-based compounds, preparation of organic compounds, etc., can solve the problems of lack of samples, low content, few synthesis and activity research reports, etc.

Pending Publication Date: 2022-02-22
INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The content of this type of compound is low in nature, and the samples are scarce. At present, there are not many reports on the synthesis and activity of this type of compound.

Method used

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  • 2,3-diarylindene derivatives, and preparation method, pharmaceutical compositions and application thereof
  • 2,3-diarylindene derivatives, and preparation method, pharmaceutical compositions and application thereof
  • 2,3-diarylindene derivatives, and preparation method, pharmaceutical compositions and application thereof

Examples

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specific Embodiment approach

[0113] In order to further clarify the present invention, a series of examples are given below, these examples are completely illustrative, they are only used to describe the present invention in detail, and should not be construed as limiting the present invention.

[0114] The synthetic route of intermediate compound 1a in the embodiment:

[0115]

Embodiment 1

[0117] 2-(3,5-dimethoxymethoxyphenyl)-3-(3-methoxy-4-methoxymethoxyphenyl)-4,6-dimethoxymethoxy-1H- Inden-1-one (1)

[0118] The synthetic route of compound 1:

[0119]

[0120] Compound 1a (5g, 9.0 12.0mmol) was dissolved in 10ml of toluene, followed by adding compound 1g (8.8g, 24.0mmol), palladium acetate (112.5mg, 0.4 0.5mmol), xphos (333.2mg, 0.7mmol) and tert-butanol Sodium (1.73g, 18mmol). React in a sealed bottle at 120° C. for 3 h, TLC detection shows that the reaction is complete, and the reaction is stopped. The reaction solution was cooled to room temperature, diluted with 50ml of water, filtered with diatomaceous earth, extracted with ethyl acetate, the organic phases were combined, washed three times with saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain 200-300 mesh silica gel column chromatography, eluting with petroleum ether: dichloromethane: acetone (...

Embodiment 2

[0123] 2-(3,5-dihydroxyphenyl)-3-(3-methoxy-4-hydroxyphenyl)-4,6-dihydroxy-1H-inden-1-one (2)

[0124] Synthetic routes of compounds 2 and 3:

[0125]

[0126] Compound 1 (100 mg, 0.163 mmol) was dissolved in 10 ml of methanol, 25 N concentrated hydrochloric acid was added, and reacted at room temperature for 10 h. TLC detection showed that the reaction was complete. Adjust the pH of the reaction solution to neutral with saturated sodium bicarbonate solution, add 20ml of water to dilute, extract with ethyl acetate, combine the organic phases, wash with saturated sodium chloride solution, dry over anhydrous magnesium sulfate, filter under reduced pressure, and decompress the filtrate concentrate. The resulting solid was chromatographed on a 200-300 mesh silica gel column and eluted with dichloromethane:methanol (10:1) to give colorless oily liquids 2 (19 mg, 30%) and 3 (9 mg, 12%).

[0127] Compound 2: black solid: 1 H NMR (400MHz, Acetone-d 6 )δ: 8.90-7.87 (5H), 7.06 (d...

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Abstract

The invention belongs to the field of biological medicine, and relates to 2,3-diarylindene derivatives as well as a preparation method, pharmaceutical compositions and application thereof, in particular to the 2,3-diaryl indene derivatives as shown in general formulas (I) and (II) and pharmaceutically acceptable salts thereof, and application of the compound monomers or the pharmaceutical compositions of the derivatives in preparation of medicines for treating inflammation and immunity related diseases.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a class of 2,3-diaryl indene derivatives or their medically acceptable salts, pharmaceutical compositions containing these derivatives and their effects on inflammation and / or inflammation-immunity application in disease treatment. Background technique [0002] Inflammation is the basis of human diseases, and it is a key link in the pathological process of diseases. However, the current anti-inflammatory drugs, such as corticosteroids and non-steroidal anti-inflammatory drugs, still have many problems in clinical application, such as easy to cause gastrointestinal discomfort, bleeding, increase the occurrence of heart disease or systemic coagulation disorders, etc. Risk of Adverse Reactions. Therefore, finding safer and more effective anti-inflammatory drugs is still an important task in the current research and development of anti-inflammatory drugs. [0003] The developmen...

Claims

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Application Information

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IPC IPC(8): C07C49/755C07C69/21C07C43/21C07C43/30A61P29/00C07C45/68C07C45/64C07C67/08C07C41/16C07C41/48A61K31/122A61K31/09A61K31/222A61P19/02A61P19/06A61P37/06A61P11/00A61P17/06A61P17/00A61P1/00A61P1/04A61P25/28A61P35/00A61P9/00A61P1/02A61P13/12A61P11/06A61P1/16
CPCC07C49/755C07C69/21C07C43/21C07C43/30A61P29/00A61P19/02A61P19/06A61P37/06A61P11/00A61P17/06A61P17/00A61P1/00A61P1/04A61P25/28A61P35/00A61P9/00A61P1/02A61P13/12A61P11/06A61P1/16C07C2602/08
Inventor 姚春所林明宝侯琦杨庆云石建功范旖瑶商昌辉袁继巧
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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