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3-phenyl-7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition

A technology of glupapentin and its derivatives, which is applied in the field of biomedicine and can solve problems such as structure-activity relationship optimization of compound systems that have not been reported in the literature.

Active Publication Date: 2019-05-07
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 research on the activity of the AmurensinH compound itself has been publicly reported by our research group, but the structure-activity relationship research on the structure optimization and anti-inflammatory activity of the compound system has not been reported in the literature so far.

Method used

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  • 3-phenyl-7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition
  • 3-phenyl-7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition
  • 3-phenyl-7,8-dehydrogenated vitis amurensis vine pentosidine derivatives as well as preparation method and pharmaceutical composition thereof and application of derivatives and pharmaceutical composition

Examples

Experimental program
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Effect test

specific Embodiment approach

[0128] 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 specifically describe the present invention, and should not be construed as limiting the present invention.

[0129] The synthetic route of compound intermediate 1b in the embodiment:

[0130]

Embodiment 1

[0132] 3-(3,5-Dimethoxyphenyl)-6-methoxy-4-benzofurancarboxylic acid (1)

[0133] The synthetic route of compound 1:

[0134]

[0135] Compound 1b (10.0g, 29.2mmol) was added to 150mL THF, MeOH and H 2 In the mixed solution of O (1:1:1, v / v / v), stir to dissolve it, and add 1.17g of NaOH. The reaction mixture was heated to reflux for 12 h, and the reaction raw materials were hydrolyzed completely. Most of the solvent was distilled off the reaction solution under reduced pressure at 42°C, and 1 mol / L HCl solution was added dropwise until no white precipitate was precipitated. The reaction mixture was suction-filtered, washed with distilled water, and dried to obtain compound 1 (9.48 g, 98.9%) as a white powdery solid.

[0136] Compound 1: white powder. 1 H NMR (500MHz, acetone-d 6 )δ7.89(s,1H),7.37(d,J=2.0Hz,1H),7.31(d,J=2.0Hz,1H),6.54(d,J=2.0Hz,2H),6.43(t, J=2.0Hz,1H), 3.94(s,3H),3.78(s,6H); 13 C NMR (125MHz, acetone-d 6 ):δ168.07,161.41,158.52, 158.15,144.22,135.64,...

Embodiment 2

[0146] 3-(3,5-Dimethoxyphenyl)-6-methoxy-4-benzofurancarboxylic acid acetic anhydride (2)

[0147] Synthesized according to method B, the alcohol compound added was 4-acetamidophenoxyethyl ester (70.6 mg, 0.36 mmol), using petroleum ether: acetone (2:1) as a developing solvent, prepared and separated on a silica gel plate to obtain the target product, Yield 79.9%. The physicochemical parameters of compound 2 are as follows:

[0148] Compound 2: off-white solid, yield=39.1%. 1 H NMR (500MHz, acetone-d 6 ):δ7.89(s,1H),7.38(d,J=2.0Hz,1H),7.24(d,J=2.0Hz,1H),6.50(s,3H),3.93(s,3H),3.81 (s,6H),3.30(s,3H); 13 C NMR (125MHz, acetone-d 6 ):δ168.04,161.79(3×C), 158.61,157.97,144.10,135.80,127.09,123.82,118.81,113.72,107.15(2×C),100.17, 100.09,56.44,55.68(2×C),51. (+)-ESI m / z:393[M+Na] + ,409[M+K] + .

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Abstract

The invention discloses a novel class of 3-phenyl-7,8-dehydrogenated vitis amurensis vine pentosidine (amurensin H) derivatives with anti-inflammatory activity and anti-inflammatory activity thereof.Specifically, the invention relates to the 3-aryl-4 substituted benzofuran derivatives with a novel structure represented by a general formula (I) shown in the description or a medically-acceptable salt of the derivatives. The invention discloses an application of the derivative monomers or the pharmaceutical composition of the derivatives in clinical treatment of inflammatory related diseases.

Description

technical field [0001] The present invention relates to the field of biomedicine, in particular to a class of 3-phenyl-7,8-dehydroglupapentin (Amurensin H) derivatives with a benzofuran structure or medically acceptable salts thereof, containing these derivatives The pharmaceutical composition of the drug and its application in the clinical treatment of inflammatory related diseases. 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 developm...

Claims

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Application Information

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IPC IPC(8): C07D307/80C07D405/12C07D405/14A61K31/343A61K31/404A61P29/00A61P37/00A61P19/02A61P19/06A61P17/06A61P37/02A61P11/00A61P17/00A61P17/02A61P1/00A61P37/08A61P1/04A61P9/10A61P1/02A61P31/00A61P1/16A61P35/00A23L33/10
Inventor 姚春所林明宝侯琦白金叶石建功张纪法范燕楠滕彬豪
Owner INST OF MATERIA MEDICA AN INST OF THE CHINESE ACAD OF MEDICAL SCI
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